Applications of Carboxylesterase Activity in Environmental Monitoring and Toxicity Identification Evaluations (TIEs)

  • Craig E. Wheelock
  • Bryn M. Phillips
  • Brian S. Anderson
  • Jeff L. Miller
  • Mike J. Miller
  • Bruce D. Hammock
Part of the Reviews of Environmental Contamination and Toxicology book series (RECT, volume 195)

The purpose of this review is to examine uses of carboxylesterase activity in environmental monitoring with a specific emphasis on pyrethroid insecticides. The chapter begins with an overview of the enzyme class, including general structure, function, catalytic mechanism, and substrate specificity. This section serves to introduce carboxylesterases, their biological significance, and their role in metabolism and detoxification reactions. Following this section, an in-depth analysis of different reports of applications of carboxylesterase activity in environmental monitoring is presented on an organism-specific basis. From an environmental standpoint, one of the most important carboxylesterase-mediated reactions is the hydrolysis and subsequent detoxification of pyrethroid insecticides. This reaction is one of the main detoxification pathways for pyrethroids in numerous organisms ranging from worms to fish to humans and is also an important pathway for the development of insect resistance to pyrethroid-associated toxicity. Accordingly, this class of insecticide is reviewed in more detail, with emphasis on toxicity and physical properties. The high hydrophobicity of pyrethroids is specifically addressed with a discussion of the effects of surface adsorption upon the observed toxicity in aquatic testing systems. A particular point is that changing agricultural practices combined with new legislation are causing a shift in insecticide usage patterns from organophosphates (OPs) and carbamates to pyrethroids. The effects of this shift are complex and potentially far reaching, especially the environmental consequences. In particular, the extreme toxicity of pyrethroids to many aquatic organisms, combined with their hydrophobicity, has resulted in concern regarding their potential environmental effects. This concern is exacerbated by the fact that current Toxicity Identification Evaluation (TIE) protocols devised for the identification of insecticides (and other environmental contaminants) in aqueous and sediment samples do not identify pyrethroid-associated toxicity with complete certainty. To address this shortfall, the use of carboxylesterase activity to hydrolyze pyrethroids in aquatic toxicity testing has been proposed as a simple, mechanistically based method to selectively identify pyrethroidassociated toxicity. This chapter reviews TIE protocols and the role of carboxylesterase activity in the development of TIE methods. A series of case studies are presented in which carboxylesterase activity was employed to identify pyrethroid-associated toxicity. Additional methods for the selective detection of pyrethroid-associated toxicity are also examined, including the use of temperature differentials and piperonyl butoxide (PBO). The strengths and weaknesses of the carboxylesterase-addition technique are also analyzed, with a number of distinct recommendations made for future development. Taken together, this review provides a detailed analysis of multiple applications of carboxylesterase to environmental monitoring and strongly advocates for further work on this enzyme system.


Esterase Activity United States Environmental Protection Agency Interstitial Water Fathead Minnow Pyrethroid Insecticide 
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  1. Abdel-Aal YAI, Hammock BD (1986) Transition state analogs as ligands for affinity purification of juvenile hormone esterase. Science 233:1073–1075.Google Scholar
  2. Abernathy CO, Casida JE (1973) Pyrethroid insecticides: esterase cleavage in relation to selective toxicity. Science 179:1235–1236.Google Scholar
  3. Adams MS, Stauber JL (2004) Development of a whole-sediment toxicity test using a benthic marine microalga. Environ Toxicol Chem 23:1957–1968.Google Scholar
  4. Ahmad M, Arif MI, Ahmad Z, Denholm I (2002) Cotton whitefly (Bemisia tabaci) resistance to organophosphate and pyrethroid insecticides in Pakistan. Pestic Manag Sci 58:203–208.Google Scholar
  5. Ahmad S, Forgash AJ (1976a) Nonoxidative enzymes in the metabolism of insecticides. Drug Metab Rev 5:141–164.Google Scholar
  6. Ahmad S, Forgash AJ (1976b) Nonoxidative enzymes in the metabolism of insecticides. Ann Clin Biochem 13:141–164.Google Scholar
  7. Al-Ghais SM, Ahmad S, Ali B (2000) Differential inhibition of xenobiotic-metabolizing carboxylesterases by organotins in marine fish. Ecotoxicol Environ Saf 46:258–264.Google Scholar
  8. Aldridge WN (1953a) Serum esterases 1. Two types of esterase (A and B) hydrolysing p-nitrophenyl acetate, propionate and butyrate, and a method for their determination. Biochem J 53:110–117.Google Scholar
  9. Aldridge WN (1953b) Serum esterases 2. An enzyme hydrolysing diethyl p-nitrophenyl phosphate (E600) and its identity with the A-esterase of mammalian sera. Biochem J 53:117–124.Google Scholar
  10. Aldridge WN (1990) An assessment of the toxicological properties of pyrethroids and their neurotoxicity. Crit Rev Toxicol 21:89–104.Google Scholar
  11. Aldridge WN (1993) The esterases: perspectives and problems. Chem Biol Interact 87:5–13.Google Scholar
  12. Amweg EL, Weston DP (2007) Whole sediment toxicity identification evaluation tools for pyrethroid insecticides: I. Piperonyl butoxide addition. Environ Toxicol Chem 26:2389–2396.Google Scholar
  13. Amweg EL, Weston DP, Ureda NM (2005) Use and toxicity of pyrethroid pesticides in the Central Valley, CA, U.S. Environ Toxicol Chem 24:966–972.Google Scholar
  14. Amweg EL, Weston DP, You J, Lydy MJ (2006) Pyrethroid insecticides and sediment toxicity in urban creeks from California and Tennessee. Environ Sci Technol 40:1700–1706.Google Scholar
  15. Anderson BS, Hunt JW, Phillips BM, Fairey R, Oakden J, Puckett HM, Stephenson M, Tjeerdema RS, Long ER, Wilson CJ, Lyons M (2001) Sediment quality in Los Angeles Harbor: a triad assessment. Environ Toxicol Chem 20:359–370.Google Scholar
  16. Anderson BS, de Vlaming V, Larson K, Deanovic LA, Birosik S, Smith DJ, Hunt JW, Phillips BM, Tjeerdema RS (2002) Causes of ambient toxicity in the Calleguas Creek watershed of southern California. Environ Monit Assess 78:131–151.Google Scholar
  17. Anderson BS, Hunt JW, Phillips BM, Nicely PA, de Vlaming V, Connor V, Richard N, Tjeerdema RS (2003) Integrated assessment of the impacts of agricultural drainwater in the Salinas River (California, USA). Environ Pollut 124:523–532.Google Scholar
  18. Anderson BS, Phillips BM, Hunt JW, Connor V, Richard N, Tjeerdema RS (2006a) Identifying primary stressors impacting macroinvertebrates in the Salinas River (California, USA): relative effects of pesticides and suspended particles. Environ Pollut 141:402–408.Google Scholar
  19. Anderson BS, Phillips BM, Hunt JW, Huntley SA, Worcester K, Richard N, Tjeerdema RS (2006b) Evidence of pesticide impacts in the Santa Maria River watershed (California, U.S.). Environ Toxicol Chem 25:1160–1170.Google Scholar
  20. Anderson BS, Lowe S, Hunt JW, Phillips BM, Voorhees JP, Clark SL, Tjeerdema RS (2007) Relative sensitivities of toxicity test protocols with the amphipods Eohaustorius estuarius and Ampelisca abdita. Ecotoxicol Environ Saf 69:24–31.Google Scholar
  21. Anderson BS, Phillips BM, Hunt JW, Voorhees JP, Clark SL, Mekebri A, Crane D, Tjeerdema RS (in press-b) Recent advances in sediment toxicity identification evaluations emphasizing pyrethroid pesticides. In: Gan J-G, Hendley P, Spurlock F, Weston D (eds) Synthetic Pyrethroids: Occurence and Behavior in Aquatic Environments. American Chemical Society, Washington, DC, in press.Google Scholar
  22. Anderson BS, Hunt JW, Phillips BM, Tjeerdema RS (2007) Navigating the TMDL Process: Sediment Toxicity. Water Environment Research Foundation, Report number 02-WSM-2.Google Scholar
  23. Ankley GT, Dierkes JR, Jensen DA, Peterson GS (1991) Piperonyl butoxide as a tool in aquatic toxicological research with organophosphate insecticides. Ecotoxicol Environ Saf 21:266–274.Google Scholar
  24. Arufe MI, Arellano JM, Garcia L, Albendin G, Sarasquete C (2007) Cholinesterase activity in gilthead seabream (Sparus aurata) larvae: characterization and sensitivity to the organophosphate azinphosmethyl. Aquat Toxicol 84:328–336.Google Scholar
  25. Attademo AM, Peltzer PM, Lajmanovich RC, Cabagna M, Fiorenza G (2007) Plasma B-esterase and glutathione S-transferase activity in the toad Chaunus schneideri (Amphibia, Anura) inhabiting rice agroecosystems of Argentina. Ecotoxicology 16:533–539.Google Scholar
  26. Babczyńska A, Wilczek G, Migula P (2006) Effects of dimethoate on spiders from metal pollution gradient. Sci Total Environ 370:352–359.Google Scholar
  27. Bacey J, Starner K, Spurlock F (2003) Preliminary Results of Study #214: Monitoring the Occurrence and Concentration of Esfenvalerate and Permethrin Pyrethroids. Department of Pesticide Regulation, Sacramento, CA.Google Scholar
  28. Bacey J, Spurlock F, Starner K, Feng H, Hsu J, White J, Tran DM (2005) Residues and toxicity of esfenvalerate and permethrin in water and sediment, in tributaries of the Sacramento and San Joaquin rivers, California, USA. Bull Environ Contam Toxicol 74:864–871.Google Scholar
  29. Bailey HC, Miller JL, Miller MJ, Dhaliwal BS (1995) Application of toxicity identification procedures to the echinoderm fertilization assay to identify toxicity in a municipal effluent. Environ Toxicol Chem 14:2181–2186.Google Scholar
  30. Bailey HC, Digiorgio C, Kroll K, Miller JL, Hinton DE, Starrett G (1996) Development of procedures for identifying pesticide toxicity in ambient waters: carbofuran, diazinon, chlorpyrifos. Environ Toxicol Chem 15:837–845.Google Scholar
  31. Bailey HC, Miller JL, Miller MJ, Wiborg LC, Deanovic LA, Shed T (1997) Joint acute toxicity of diazinon and chlorpyrifos to Ceriodaphnia dubia. Environ Toxicol Chem 16:2304–2308.Google Scholar
  32. Bailey HC, Deanovic LA, Reyes E, Kimball T, Larson K, Cortright K, Connor V, Hinton DE (2000) Diazinon and chlorpyrifos in urban waterways in Northern California, USA. Environ Toxicol Chem 19:82–87.Google Scholar
  33. Baker CMA, Manwell C, Labisky RF, Harper JA (1966) Molecular genetics of avian proteins. V. Egg, blood and tissue proteins of the ring necked pheasant Phasianius colchius. Comp Biochem Physiol 17:467–499.Google Scholar
  34. Barata C, Solayan A, Porte C (2004) Role of B-esterases in assessing toxicity of organophosphorus (chlorpyrifos, malathion) and carbamate (carbofuran) pesticides to Daphnia magna. Aquat Toxicol 66:125–139.Google Scholar
  35. Barata C, Damasio J, Angel López M, Kuster M, López de Alda M, Barceló D, Carmen Riva M, Raldúa D (2007) Combined use of biomarkers and in situ bioassays in Daphnia magna to monitor environmental hazards of pesticides in the field. Environ Toxicol Chem 26:370–379.Google Scholar
  36. Barron MG, Charron KA, Stott WT, Duvall SE (1999) Tissue carboxylesterase activity of rainbow trout. Environ Toxicol Chem 18:2506–2511.Google Scholar
  37. Bartkowiak DJ, Wilson BW (1995) Avian plasma carboxylesterase activity as a potential biomarker of organophosphate pesticide exposure. Environ Toxicol Chem 14:2149–2153.Google Scholar
  38. Basack SB, Oneto ML, Fuchs JS, Wood EJ, Kesten EM (1998) Esterases of Corbicula fluminea as biomarkers of exposure to organophosphorus pesticides. Bull Environ Contam Toxicol 61:569–576.Google Scholar
  39. Bencharit S, Morton CL, Howard-Williams EL, Danks MK, Potter PM, Redinbo MR (2002) Structural insights into CPT-11 activation by mammalian carboxylesterases. Nat Struct Biol 9:337–342.Google Scholar
  40. Bencharit S, Morton CL, Hyatt JL, Kuhn P, Danks MK, Potter PM, Redinbo MR (2003a) Crystal structure of human carboxylesterase 1 complexed with the Alzheimer’s drug tacrine: from binding promiscuity to selective inhibition. Chem Biol 10:341–349.Google Scholar
  41. Bencharit S, Morton CL, Xue Y, Potter PM, Redinbo MR (2003b) Structural basis of heroin and cocaine metabolism by a promiscuous human drug-processing enzyme. Nat Struct Biol 10:349–356.Google Scholar
  42. Bencharit S, Edwards CC, Morton CL, Howard-Williams EL, Kuhn P, Potter PM, Redinbo MR (2006) Multisite promiscuity in the processing of endogenous substrates by human carboxylesterase 1. J Mol Biol 363:201–214.Google Scholar
  43. Besser JM, Ingersoll CG, Leonard EN, Mount DR (1998) Effect of zeolite on toxicity of ammonia in freshwater sediments: implications for toxicity identification evaluation procedures. Environ Toxicol Chem 17:2310–2317.Google Scholar
  44. Blaise C, Ménard L (1998) A micro-algal solid-phase test to assess the toxic potential of freshwater sediments. Water Qual Res J Can 33:133–151.Google Scholar
  45. Bloomquist JR, Adams PM, Soderlund DM (1986) Inhibition of gamma-aminobutyric acid-stimulated chloride flux in mouse brain vesicles by polychlorocycloalkane and pyrethroid insecticides. Neurotoxicology 7:11–20.Google Scholar
  46. Bodor N, Buchwald P (2000) Soft drug design: general principles and recent applications. Med Res Rev 20:58–101.Google Scholar
  47. Bodor N, Buchwald P (2003) Retrometabolism-based drug design and targeting. In: Abraham D (ed) Burger’s Medicinal Chemistry and Drug Discovery, 6th Ed. Vol 2, Wiley, New York, pp 534–596.Google Scholar
  48. Bodor N, Buchwald P (2004) Designing safer (soft) drugs by avoiding the formation of toxic and oxidative metabolites. Mol Biotechnol 26:123–132.Google Scholar
  49. Bonacci S, Browne MA, Dissanayake A, Hagger JA, Corsi I, Focardi S, Galloway TS (2004) Esterase activities in the bivalve mollusc Adamussium colbecki as a biomarker for pollution monitoring in the Antarctic marine environment. Mar Pollut Bull 49:445–455.Google Scholar
  50. Bond J-A, Bradley BP (1997) Resistance to malathion in heat-shocked Daphnia magna. Environ Toxicol Chem 16:705–712.Google Scholar
  51. Bondarenko S, Putt A, Kavanaugh S, Poletika N, Gan J (2006) Time dependence of phase distribution of pyrethroid insecticides in sediment. Environ Toxicol Chem 25:3148–3154.Google Scholar
  52. Bornscheuer UT (2002) Microbial carboxyl esterases: classification, properties and application in biocatalysis. FEMS Microbiol Rev 26:73–81.Google Scholar
  53. Bradberry SM, Cage SA, Proudfoot AT, Vale JA (2005) Poisoning due to pyrethroids. Toxicol Rev 24:93–106.Google Scholar
  54. Bradbury SP, Coats JR (1989a) Toxicokinetics and toxicodynamics of pyrethroid insecticides in fish. Environ Toxicol Chem 8:373–380.Google Scholar
  55. Bradbury SP, Coats JR (1989b) Comparative toxicology of the pyrethroid insecticides. Rev Environ Contam Toxicol 108:133–177.Google Scholar
  56. Brodbeck U, Schweikert K, Gentinetta R, Rottenberg M (1979) Fluorinated aldehydes and ketones acting as quasi-substrate inhibitors of acetylcholinesterase. Biochim Biophys Acta 567:357–369.Google Scholar
  57. Brooks GT (1986) Insecticide metabolism and selective toxicity. Xenobiotica 16:989–1002.Google Scholar
  58. Burgess RM, Charles JB, Kuhn A, Ho KT, Patton LE, McGovern DG (1997) Development of a cation-exchange methodology for marine toxicity identification evaluation applications. Environ Toxicol Chem 16:1203–1211.Google Scholar
  59. Burgess RM, Cantwell MG, Pelletier MC, Ho KT, Serbst JR, Cook H, Kuhn A (2000) Development of a toxicity identification evaluation procedure for characterizing metal toxicity in marine sediments. Environ Toxicol Chem 19:982–991.Google Scholar
  60. Burgess RM, Pelletier MC, Ho KT, Serbst JR, Ryba SA, Kuhn A, Perron MM, Raczelowski P, Cantwell MG (2003) Removal of ammonia toxicity in marine sediment TIEs: a comparison of Ulva lactuca, zeolite and aeration methods. Mar Pollut Bull 46:607–618.Google Scholar
  61. Burgess RM, Perron MM, Cantwell MG, Ho KT, Serbst JR, Pelletier MC (2004) Use of zeolite for removing ammonia and ammonia-caused toxicity in marine toxicity identification evaluations. Arch Environ Contam Toxicol 47:440–447.Google Scholar
  62. Butte W, Kemper K (1999) A spectrophotometric assay for pyrethroid-cleaving enzymes in human serum. Toxicol Lett 107:4953.Google Scholar
  63. Byrne FJ, Gorman KJ, Cahill M, Denholm I, Devonshire AL (2000) The role of B-type esterases in conferring insecticide resistance in the tobacco whitefly, Bemisia tabaci (Genn). Pestic Manag Sci 56:867–874.Google Scholar
  64. Cahill M, Byrne FJ, German K, Denholm I, Devonshire AL (1995) Pyrethroid and organophosphate resistance in the Tobacco Whitefly Bemisia tabaci (Homoptera, Aleyrodidae). B Entomol Res 85:181–187.Google Scholar
  65. Casida JE (1970) Mixed-function oxidase involvement in the biochemistry of insecticide synergists. J Agric Food Chem 18:753–772.Google Scholar
  66. Casida JE (1973) Pyrethrum, the Natural Insecticide. Academic Press, New York.Google Scholar
  67. Casida JE (1980) Pyrethrum flowers and pyrethroid insecticides. Environ Health Perspect 34:189–202.Google Scholar
  68. Casida JE, Quistad GB (1995) Metabolism and synergism of pyrethrins. In: Casida JE, Quistad GB (eds) Pyrethrum Flowers: Production, Chemistry, Toxicology, and Uses, 1st Ed. Oxford University Press, New York, pp 258–276.Google Scholar
  69. Casida JE, Quistad GB (1998) Golden age of insecticide research: past, present, or future? Annu Rev Entomol 43:1–16.Google Scholar
  70. Casida JE, Quistad GB (2004) Organophosphate toxicology: safety aspects of nonacetylcholinesterase secondary targets. Chem Res Toxicol 17:983–998.Google Scholar
  71. Casida JE, Quistad GB (2005) Serine hydrolase targets of organophosphorus toxicants. Chem Biol Interact 157–158:277–283.Google Scholar
  72. Casida JE, Gammon DW, Glickman AH, Lawrence LJ (1983) Mechanisms of selective action of pyrethroid insecticides. Annu Rev Pharmacol Toxicol 23:413–438.Google Scholar
  73. Castellanos LC, Sanchez-Hernandez JC (2007) Earthworm biomarkers of pesticide contamination: current status and perspectives. J Pestic Sci 32:360–371.Google Scholar
  74. Chambers JE (1976) The relationship of esterases to organophosphorus insecticide tolerance in mosquitofish. Pestic Biochem Physiol 6:517–522.Google Scholar
  75. Chevre N, Gagne F, Blaise C (2003) Development of a biomarker-based index for assessing the ecotoxic potential of aquatic sites. Biomarkers 8:287–298.Google Scholar
  76. Chiang SW, Sun CN (1996) Purification and characterization of carboxylesterases of rice green leafhopper Nephotettix cincticeps Uhler. Pest Biochem Physiol 54:181–189.Google Scholar
  77. Choi J, Hodgson E, Rose RL (2004) Inhibition of trans-permethrin hydrolysis in human liver fractions by chloropyrifos oxon and carbaryl. Drug Metab Drug Interact 20:233–246.Google Scholar
  78. Coats JR (1990) Mechanisms of toxic action and structure-activity relationships for organochlorine and synthetic pyrethroid insecticides. Environ Health Perspect 87:255–262.Google Scholar
  79. Coats JR, Symonik DM, Bradbury SP, Dyer SD, Timson LK, Atchison GJ (1989) Toxicology of synthetic pyrethroids in aquatic organisms: an overview. Environ Toxicol Chem 8:671–679.Google Scholar
  80. Coleman M, Hemingway J (2007) Insecticide resistance monitoring and evaluation in disease transmitting mosquitoes. J Pestic Sci 32:69–76.Google Scholar
  81. Cordi B, Fossi C, Depledge MH (1997) Temporal biomarker responses in wild passerine birds exposed to pesticide spray drift. Environ Toxicol Chem 16:2118–2124.Google Scholar
  82. Corsi I, Bonacci S, Santovito G, Chiantore M, Castagnolo L, Focardi S (2004) Cholinesterase activities in the Antarctic scallop Adamussium colbecki: tissue expression and effect of ZnCl2 exposure. Mar Environ Res 58:401–406.Google Scholar
  83. Cui F, Weill M, Berthomieu A, Raymond M, Qiao CL (2007) Characterization of novel esterases in insecticide-resistant mosquitoes. Insect Biochem Mol Biol 37:1131–1137.Google Scholar
  84. Curtis CF, Mnzava AE (2000) Comparison of house spraying and insecticide-treated nets for malaria control. Bull W H O 78:1389–1400.Google Scholar
  85. Cygler M, Schrag JD, Sussman JL, Harel M, Silman I, Gentry MK, Doctor BP (1993) Relationship between sequence conservation and three-dimensional structure in a large family of esterases, lipases, and related proteins. Protein Sci 2:366–382.Google Scholar
  86. Davies JH (1985) The pyrethroids: an historical introduction. In: Leahey JP (ed) The Pyrethroid Insecticides. Taylor & Francis, Philadelphia, pp 1–41.Google Scholar
  87. Day KE (1989) Acute, chronic and sublethal effects of synthetic pyrethroids on freshwater zooplankton. Environ Toxicol Chem 8:411–416.Google Scholar
  88. Denton D (2001) Integrated Toxicological and Hydrological Assessments of Diazinon and Esfenvalerate. PhD dissertation. University of California Davis, Davis.Google Scholar
  89. Denton DL, Wheelock CE, Murray S, Deanovic LA, Hammock BD, Hinton DE (2003) Joint acute toxicity of esfenvalerate and diazinon to fathead minnow (Pimephales promelas) larvae. Environ Toxicol Chem 22:336–341.Google Scholar
  90. Dettbarn WD, Yang ZP, Milatovic D (1999) Different role of carboxylesterases in toxicity and tolerance to paraoxon and DFP. Chem Biol Interact 119–120:445–454.Google Scholar
  91. de Vlaming V, Connor V, DeGiorgio C, Bailey HC, Deanovic LA, Hinton DE (2000) Application of whole effluent toxicity test procedures to ambient water quality assessment. Environ Toxicol Chem 19:42–62.Google Scholar
  92. Devonshire AL, Heidari R, Huang HZ, Hammock BD, Russell RJ, Oakeshott JG (2007) Hydrolysis of individual isomers of fluorogenic pyrethroid analogs by mutant carboxylesterases from Lucilia cuprina. Insect Biochem Mol Biol 37:891–902.Google Scholar
  93. Elliott M (1976) Properties and applications of pyrethroids. Environ Health Perspect 14:1–2.Google Scholar
  94. Elliott M, Janes NF, Jeffs KA, Needham PH, Sawicki RM (1965) New pyrethrin-like esters with high insecticidal activity. Nature (Lond) 207:938–940.Google Scholar
  95. Elliott M, Farnham AW, Janes NF, Needham PH, Pearson BC (1967) 5-Benzyl-3-furylmethyl chrysanthemate: a new potent insecticide. Nature (Lond) 213:493–494.Google Scholar
  96. Elliott M, Farnham AW, Janes NF, Needham PH, Pulman DA (1973a) Potent pyrethroid insecticides from modified cyclopropane acids. Nature (Lond) 244:456–457.Google Scholar
  97. Elliott M, Farnham AW, Janes NF, Needham PH, Pulman DA, Stevenson JH (1973b) A photostable pyrethroid. Nature (Lond) 246:169–170.Google Scholar
  98. Elliott M, Farnham AW, Janes NF, Needham PH, Pulman DA (1974) Synthetic insecticide with a new order of activity. Nature (Lond) 248:710–711.Google Scholar
  99. Elzen GW, Leonard BR, Graves JB, Burris E, Micinski S (1992) Resistance to pyrethroid, carbamate, and organophosphate insecticides in field populations of Tobacco Budworm (Lepidoptera, Noctuidae) in 1990. J Econ Entomol 85:2064–2072.Google Scholar
  100. Enan E, Matsumura F (1993) Activation of phosphoinositide/protein kinase C pathway in rat brain tissue by pyrethroids. Biochem Pharmacol 45:703–710.Google Scholar
  101. Enayati AA, Ranson H, Hemingway J (2005) Insect glutathione transferases and insecticide resistance. Insect Mol Biol 14:3–8.Google Scholar
  102. Epstein L, Bassein S, Zalom FG (2000) Almond and stone fruit growers reduce OP, increase pyrethroid use in dormant sprays. Calif Agric 54:14–19.Google Scholar
  103. Escartin E, Porte C (1997) The use of cholinesterase and carboxylesterase activities from Mytilus galloprovincialis in pollution monitoring. Environ Toxicol Chem 16:2090–2095.Google Scholar
  104. Ferrari A, Venturino A, Pechén de D’Angelo AM (2007) Effects of carbaryl and azinphos-methyl on juvenile rainbow trout (Oncorhynchus mykiss) detoxifying enzymes. Pestic Biochem Physiol 88:134–142.Google Scholar
  105. Fleming CD, Bencharit S, Edwards CC, Hyatt JL, Tsurkan L, Bai F, Fraga C, Morton CL, Howard-Williams EL, Potter PM, Redinbo MR (2005) Structural insights into drug processing by human carboxylesterase. 1: Tamoxifen, mevastatin, and inhibition by benzil. J Mol Biol 352:165–177.Google Scholar
  106. Fleming CD, Edwards CC, Kirby SD, Maxwell DM, Potter PM, Cerasoli DM, Redinbo MR (2007) Crystal structures of human carboxylesterase 1 in covalent complexes with the chemical warfare agents Soman and Tabun. Biochemistry 46:5063–5071.Google Scholar
  107. Forshaw PJ, Lister T, Ray DE (1993) Inhibition of a neuronal voltage-dependent chloride channel by the type II pyrethroid, deltamethrin. Neuropharmacology 32:105–111.Google Scholar
  108. Fossi MC, Leonzio C, Massi A, Lari L, Casini S (1992) Serum esterase inhibition in birds: a nondestructive biomarker to assess organophosphorus and carbamate contamination. Arch Environ Contam Toxicol 23:99–104.Google Scholar
  109. Fossi MC, Massi A, Leonzio C (1994) Blood esterase inhibition in birds as an index of organophosphorus contamination: field and laboratory studies. Ecotoxicology 3:11–20.Google Scholar
  110. Fossi MC, Sanchez-Hernandez JC, Diaz-Diaz R, Lari L, Garcia-Hernandez JE, Gaggi C (1995) The lizard Gallotia galloti as a bioindicator of organophosphorus contamination in the Canary Islands. Environ Pollut 87:289–294.Google Scholar
  111. Fossi MC, Lari L, Casini S (1996) Interspecies variation of “B” esterases in birds: the influence of size and feeding habits. Arch Environ Contam Toxicol 31:525532.Google Scholar
  112. Fourcy D, Jumel A, Heydorff M, Lagadic L (2002) Esterases as biomarkers in Nereis (Hediste) diversicolor exposed to temephos and Bacillus thuringiensis var. israelensis used for mosquito control in coastal wetlands of Morbihan (Brittany, France). Mar Environ Res 54:755–759.Google Scholar
  113. Fournier D, Bride JM, Poirie M, Berge JB, Plapp FW Jr (1992) Insect glutathione S-transferases. Biochemical characteristics of the major forms from houseflies susceptible and resistant to insecticides. J Biol Chem 267:1840–1845.Google Scholar
  114. Fujitani Y (1909) Chemistry and pharmacology of insect powder. Arch Exp Pathol Pharmacol 61:47–75.Google Scholar
  115. Fukuto TR (1990) Mechanism of action of organophosphorus and carbamate insecticides. Environ Health Perspect 87:245–254.Google Scholar
  116. Fulton MH, Key PB (2001) Acetylcholinesterase inhibition in estuarine fish and invertebrates as an indicator of organophosphorus insecticide exposure and effects. Environ Toxicol Chem 20:37–45.Google Scholar
  117. Galloway TS (2006) Biomarkers in environmental and human health risk assessment. Mar Pollut Bull 53:606–613.Google Scholar
  118. Galloway TS, Millward N, Browne MA, Depledge MH (2002) Rapid assessment of organophosphorous/carbamate exposure in the bivalve mollusc Mytilus edulis using combined esterase activities as biomarkers. Aquat Toxicol 61:169–180.Google Scholar
  119. Galloway TS, Brown RJ, Browne MA, Dissanayake A, Lowe D, Jones MB, Depledge MH (2004a) Ecosystem management bioindicators: the ECOMAN project: a multi-biomarker approach to ecosystem management. Mar Environ Res 58:233–237.Google Scholar
  120. Galloway TS, Brown RJ, Browne MA, Dissanayake A, Lowe D, Jones MB, Depledge MH (2004b) A multibiomarker approach to environmental assessment. Environ Sci Technol 38:1723–1731.Google Scholar
  121. Galloway TS, Brown RJ, Browne MA, Dissanayake A, Lowe D, Depledge MH, Jones MB (2006) The ECOMAN project: A novel approach to defining sustainable ecosystem function. Mar Pollut Bull 53:186–194.Google Scholar
  122. Gan J, Lee SJ, Liu WP, Haver DL, Kabashima JN (2005) Distribution and persisitence of pyrethroids in runoff sediments. J Environ Qual 34:836–841.Google Scholar
  123. Gaughan LC, Engel JL, Casida JE (1980) Pestcide interactions: effects of organophosphorus pesticides on the metabolism, toxicity, and persistence of selected pyrethroid insecticides. Pestic Biochem Physiol 14:81–85.Google Scholar
  124. Gershater M, Sharples K, Edwards R (2006) Carboxylesterase activities toward pesticide esters in crops and weeds. Phytochemistry 67:2561–2567.Google Scholar
  125. Glade MJ (1998) The Food Quality Protection Act of 1996. Nutrition 14:65–66.Google Scholar
  126. Glickman AH, Casida JE (1982) Species and structural variations affecting pyrethroid neurotoxicity. Neurobehav Toxicol Teratol 4:793–799.Google Scholar
  127. Glickman AH, Lech JJ (1981) Hydrolysis of permethrin, a pyrethroid insecticide, by rainbow trout and mouse tissues in vitro: a comparative study. Toxicol Appl Pharmacol 60:186–192.Google Scholar
  128. Glickman AH, Lech JJ (1982) Differential toxicity of trans-permethrin in rainbow trout and mice. II. Role of target organ sensitivity. Toxicol Appl Pharmacol 66:162–171.Google Scholar
  129. Glickman AH, Shono T, Casida JE, Lech JJ (1979) In vitro metabolism of permethrin isomers by carp and rainbow trout liver microsomes. J Agric Food Chem 27:1038–1041.Google Scholar
  130. Glickman AH, Weitman SD, Lech JJ (1982) Differential toxicity of trans-permethrin in rainbow trout and mice. I. Role of biotransformation. Toxicol Appl Pharmacol 66:153–161.Google Scholar
  131. Greenwood BM, Bojang K, Whitty CJ, Targett GA (2005) Malaria. Lancet 365:1487–1498.Google Scholar
  132. Gupta RC, Dettbarn WD (1993) Role of carboxylesterases in the prevention and potentiation of N-methylcarbamate toxicity. Chem-Biol Interact 87:295–303.Google Scholar
  133. Gupta RC, Kadel WL (1990) Toxic interaction of tetraisopropylpyrophosphoramide and propoxur: some insights into the mechanisms. Arch Environ Contam Toxicol 19:917–920.Google Scholar
  134. Hamers T, Molin KR, Koeman JH, Murk AJ (2000) A small-volume bioassay for quantification of the esterase inhibiting potency of mixtures of organophosphate and carbamate insecticides in rainwater: development and optimization. Toxicol Sci 58:60–67.Google Scholar
  135. Hamers T, van den Brink PJ, Mos L, van der Linden SC, Legler J, Koeman JH, Murk AJ (2003) Estrogenic and esterase-inhibiting potency in rainwater in relation to pesticide concentrations, sampling season and location. Environ Pollut 123:47–65.Google Scholar
  136. Hamm JT, Wilson BW, Hinton DE (2001) Increasing uptake and bioactivation with development positively modulate diazinon toxicity in early life stage medaka (Oryzias latipes). Toxicol Sci 61:304–313.Google Scholar
  137. Hannam ML, Hagger JA, Jones MB, Galloway TS (in press) Characterisation of esterases as potential biomarkers of pesticide exposure in the lugworm Arenicola marina (Annelida: Polychaeta). Environ Pollut in press.Google Scholar
  138. Harold JA, Ottea JA (2000) Characterization of esterases associated with profenofos resistance in the tobacco budworm, Heliothis virescens (F.). Arch Insect Biochem Physiol 45:47–59.Google Scholar
  139. He F, Wang S, Liu L, Chen S, Zhang Z, Sun J (1989) Clinical manifestations and diagnosis of acute pyrethroid poisoning. Arch Toxicol 63:54–58.Google Scholar
  140. Heikinheimo P, Goldman A, Jeffries C, Ollis DL (1999) Of barn owls and bankers: a lush variety of alpha/beta hydrolases. Structure Fold Descr 7:R141–146.Google Scholar
  141. Hemingway J, Karunaratne SH (1998) Mosquito carboxylesterases: a review of the molecular biology and biochemistry of a major insecticide resistance mechanism. Med Vet Entomol 12:1–12.Google Scholar
  142. Hicks LD, Hyatt JL, Moak T, Edwards CC, Tsurkan L, Wierdl M, Ferreira AM, Wadkins RM, Potter PM (2007) Analysis of the inhibition of mammalian carboxylesterases by novel fluorobenzoins and fluorobenzils. Bioorg Med Chem 15:3801–3817.Google Scholar
  143. Ho KT, Kuhn A, Pelletier MC, McGee F, Burgess RM, Serbst JR (2000) Sediment toxicity assessment: comparison of standard and new testing designs. Arch Environ Contam Toxicol 39:462–468.Google Scholar
  144. Ho KT, Kuhn A, Pelletier MC, Serbst JR, Cook H, Cantwell MG, Ryba SA, Perron MM, Lebo J, Huckins J, Petty J (2004) Use of powdered coconut charcoal as a toxicity identification and evaluation manipulation for organic toxicants in marine sediments. Environ Toxicol Chem 23:2124–2131.Google Scholar
  145. Hodgson E (1982) Production of pesticide metabolites by oxidative reactions. J Toxicol Clin Toxicol 19:609–621.Google Scholar
  146. Hosokawa M, Endo T, Fujisawa M, Hara S, Iwata N, Sato Y, Satoh T (1995) Interindividual variation in carboxylesterase levels in human liver microsomes. Drug Metab Dispos 23:1022–1027.Google Scholar
  147. Hosokawa M, Furihata T, Yaginuma Y, Yamamoto N, Koyano N, Fujii A, Nagahara Y, Satoh T, Chiba K (2007) Genomic structure and transcriptional regulation of the rat, mouse, and human carboxylesterase genes. Drug Metab Rev 39:1–15.Google Scholar
  148. Hotelier T, Renault L, Cousin X, Negre V, Marchot P, Chatonnet A (2004) ESTHER, the database of the alpha/beta-hydrolase fold superfamily of proteins. Nucleic Acids Res 32(database issue):D145–D147.Google Scholar
  149. Huang H, Ottea JA (2004) Development of pyrethroid substrates for esterases associated with pyrethroid resistance in the tobacco budworm, Heliothis virescens (F.). J Agric Food Chem 52:6539–6545.Google Scholar
  150. Huang H, Fleming CD, Nishi K, Redinbo MR, Hammock BD (2005) Stereoselective hydrolysis of pyrethroid-like fluorescent substrates by human and other mammalian liver carboxylesterases. Chem Res Toxicol 18:1371–1377.Google Scholar
  151. Huang H, Nishi K, Gee SJ, Hammock BD (2006) Evaluation of chiral alpha-cyanoesters as general fluorescent substrates for screening enantioselective esterases. J Agric Food Chem 54:694–699.Google Scholar
  152. Huang TL, Obih PO, Jaiswal R, Hartley WR, Thiyagarajah A (1997) Evaluation of liver and brain esterases in the spotted gar fish (Lepisosteus oculatus) as biomarkers of effect in the lower Mississippi River Basin. Bull Environ Contam Toxicol 58:688–695.Google Scholar
  153. Hunt JW, Anderson BS, Phillips BM, Tjeerdema RS, Taberski KM, Wilson CJ, Puckett HM, Stephenson M, Fairey R, Oakden J (2001) A large-scale categorization of sites in San Francisco Bay, USA, based on the sediment quality triad, toxicity identification evaluations, and gradient studies. Environ Toxicol Chem 20:1252–1265.Google Scholar
  154. Hunt JW, Anderson BS, Phillips BM, Nicely PN, Tjeerdema RS, Puckett HM, Stephenson M, Worcester K, De Vlaming V (2003) Ambient toxicity due to chlorpyrifos and diazinon in a central California coastal watershed. Environ Monit Assess 82:83–112.Google Scholar
  155. Hyatt JL, Stacy V, Wadkins RM, Yoon KJ, Wierdl M, Edwards CC, Zeller M, Hunter AD, Danks MK, Crundwell G, Potter PM (2005) Inhibition of carboxylesterases by benzil (diphenylethane-1, 2-dione) and heterocyclic analogues is dependent upon the aromaticity of the ring and the flexibility of the dione moiety. J Med Chem 48:5543–5550.Google Scholar
  156. Hyatt JL, Moak T, Hatfield MJ, Tsurkan L, Edwards CC, Wierdl M, Danks MK, Wadkins RM, Potter PM (2007) Selective inhibition of carboxylesterases by isatins, indole-2, 3-diones. J Med Chem 50:1876–1885.Google Scholar
  157. Hyne RV, Maher WA (2003) Invertebrate biomarkers: links to toxicosis that predict population decline. Ecotoxicol Environ Saf 54:366–374.Google Scholar
  158. Ileperuma NR, Marshall SD, Squire CJ, Baker HM, Oakeshott JG, Russell RJ, Plummer KM, Newcomb RD, Baker EN (2007) High-resolution crystal structure of plant carboxylesterase AeCXE1, from Actinidia eriantha, and its complex with a high-affinity inhibitor paraoxon. Biochemistry 46:1851–1859.Google Scholar
  159. Imai T (2006) Human carboxylesterase isozymes: catalytic properties and rational drug design. Drug Metab Pharmacokinet 21:173–185.Google Scholar
  160. Immaraju JA, Morse JG, Gaston LK (1990) Mechanisms of organophosphate, pyrethroid, and DDT resistance in Citrus Thrips (Thysanoptera, Thripidae). J Econ Entomol 83:1723–1732.Google Scholar
  161. James MO (1986) Overview of in vitro metabolism of drugs by aquatic species. Vet Hum Toxicol 28(suppl 1):2–8.Google Scholar
  162. Junge W, Krisch K (1975) The carboxylesterases/amidases of mammalian liver and their possible significance. Crit Rev Food Sci 371:434.Google Scholar
  163. Kakko I, Toimela T, Tähti H (2000) Piperonyl butoxide potentiates the synaptosome ATPase inhibiting effect of pyrethrin. Chemosphere 40:301–305.Google Scholar
  164. Kao L, Motoyama N, Dauterman W (1985) Multiple forms of esterases in mouse, rat, and rabbit liver, and their role in hydrolysis of organophosphate and pyrethroid insecticides. Pestic Biochem Physiol 23:66–73.Google Scholar
  165. Karpouzas DG, Singh BK (2006) Microbial degradation of organophosphorus xenobiotics: metabolic pathways and molecular basis. Adv Microb Physiol 51:119–1185.Google Scholar
  166. Katsuda Y (1999) Development of and future prospects for pyrethroid chemistry. Pestic Sci 55:775–782.Google Scholar
  167. Keizer J, D’Agostino G, Nagel R, Volpe T, Gnemi P, Vittozzi L (1995) Enzymological differences of AChE and diazinon hepatic metabolism: correlation of in vitro data with the selective toxicity of diazinon to fish species. Sci Total Environ 171:213–220.Google Scholar
  168. Kelley K, Starner K (2004) Preliminary Results for Study 219: Monitoring Surface Waters and Sediments of the Salinas and San Joaquin River Basins for Synthetic Pyrethroid Pesticides. Department of Pesticide Regulation, Sacramento, CA.Google Scholar
  169. Kingsbury N, Masters CJ (1972) Heterogeneity, molecular weight interrelationships and developmental genetics of the esterase isoenzymes of the rainbow trout. Biochim Biophys Acta 258:455–465.Google Scholar
  170. Kosian PA, West CW, Pasha MS, Cox JS, Mount DR, Huggett RJ, Ankley GT (1999) Use of nonpolar resin for reduction of fluoranthene bioavailability in sediment. Environ Toxicol Chem 18:201–206.Google Scholar
  171. Kulkarni AP, Hodgson E (1984) The metabolism of insecticides: the role of monooxygenase enzymes. Annu Rev Pharmacol Toxicol 24:19–42.Google Scholar
  172. Kuster E (2005) Cholin- and carboxyl-esterase activities in developing zebrafish embryos (Danio rerio) and their potential use for insecticide hazard assessment. Aquat Toxicol 75:76–85.Google Scholar
  173. Kuster E, Altenburger R (2006) Comparison of cholin- and carboxyl-esterase enzyme inhibition and visible effects in the zebra fish embryo bioassay under short-term paraoxon-methyl exposure. Biomarkers 11:341–354.Google Scholar
  174. LaForge FB, Barthel WF (1945) Constituents of pyrethrum flowers. XVIII. The structure and isomerism of pyrethrolone and cinerolone. J Org Chem 10:114–120.Google Scholar
  175. Lari L, Massi A, Fossi MC, Casini S, Leonzio C, Focardi S (1994) Evaluation of toxic effects of the organophosphorus insecticide azinphos-methyl in experimentally and naturally exposed birds. Arch Environ Contam Toxicol 26:234–239.Google Scholar
  176. Laskowski DA (2002) Physical and chemical properties of pyrethroids. Rev Environ Contam Toxicol 174:49–170.Google Scholar
  177. Lebo JA, Huckins JN, Petty JD, Ho KT (1999) Removal of organic contaminant toxicity from sediments: early work toward development of a toxicity identification evaluation (TIE) method. Chemosphere 39:389–406.Google Scholar
  178. Lebo JA, Huckins JN, Petty JD, Cranor WL, Ho KT (2003) Comparisons of coarse and fine versions of two carbons for reducing the bioavailabilities of sediment-bound hydrophobic organic contaminants. Chemosphere 50:1309–1317.Google Scholar
  179. Lee H-J, Shan G, Watanabe T, Stoutamire DW, Gee SJ, Hammock BD (2002) Enzyme-linked immunosorbent assay for the pyrethroid deltamethrin. J Agric Food Chem 50:5526–5532.Google Scholar
  180. Lee H-J, Shan G, Ahn K, Park E-K, Watanabe T, Gee SJ, Hammock BD (2004) Development of an enzyme-linked immunosorbent assay for the pyrethroid cypermethrin. J Agric Food Chem 52:1039–1043.Google Scholar
  181. Lee S, Gan J, Kabashima J (2002) Recovery of synthetic pyrethroids in water samples during storage and extraction. J Agric Food Chem 50:7194–7198.Google Scholar
  182. Leng G, Lewalter J, Rohrig B, Idel H (1999) The influence of individual susceptibility in pyrethroid exposure. Toxicol Lett 107:123–130.Google Scholar
  183. Li SN, Fan DF (1996) Correlation between biochemical parameters and susceptibility of freshwater fish to malathion. J Toxicol Environ Health 48:413–418.Google Scholar
  184. Li SN, Fan DF (1997) Activity of esterases from different tissues of freshwater fish and responses of their isoenzymes to inhibitors. J Toxicol Environ Health 51:149–157.Google Scholar
  185. Liu W, Gan JJ, Lee S, Kabashima JN (2004) Phase distribution of synthetic pyrethroids in runoff and stream water. Environ Toxicol Chem 23:7–11.Google Scholar
  186. Lydy MJ, Beldin J, Wheelock CE, Hammock BD, Denton DL (2004) Challenges in regulating pesticide mixtures. Ecology and Society 9:1. [online] Scholar
  187. Mak SK, Shan G, Lee H-J, Watanabe T, Stoutamire DW, Gee SJ, Hammock BD (2005) Development of a class selective immunoassay for the type II pyrethroid insecticides. Anal Chim Acta 534:109–120.Google Scholar
  188. Martin T, Ochou OG, Vaissayre M, Fournier D (2003) Organophosphorus insecticides synergize pyrethroids in the resistant strain of cotton bollworm, Helicoverpa armigera (Hubner) (Lepidoptera: Noctuidae) from West Africa. J Econ Entomol 96:468–474.Google Scholar
  189. Maund SJ, Hamer MJ, Lane MCG, Farrelly E, Rapley JH, Goggin UM, Gentle WE (2002) Partitioning, bioavailability, and toxicity of the pyrethroid insecticide cypermethrin in sediments. Environ Toxicol Chem 21:9–15.Google Scholar
  190. Maxwell DM (1992a) Detoxification of organophosphorus compounds by carboxylesterase. In: Chambers JE, Levi PE (eds) Organophosphates: Chemistry, Fate, and Effects. Academic Press, San Diego, pp 183–199.Google Scholar
  191. Maxwell DM (1992b) The specificity of carboxylesterase protection against the toxicity of organophosphate compounds. Toxicol Appl Pharmacol 114:306–312.Google Scholar
  192. Maxwell DM, Lieske CN, Brecht KM (1994) Oxime-induced reactivation of carboxylesterase inhibited by organophosphorus compounds. Chem Res Toxicol 7:428–433.Google Scholar
  193. Maxwell DM, Brecht KM (2001) Carboxylesterase: specificity and spontaneous reactivation of an endogenous scavenger for organophosphorus compounds. J Appl Toxicol 21(suppl 1):S103–S107.Google Scholar
  194. Mazzarri MB, Georghiou GP (1995) Characterization of resistance to organophosphate, carbamate, and pyrethroid insecticides in field populations of Aedes aegypti from Venezuela. J Am Mosquito Control Assoc 11:315–322.Google Scholar
  195. McAbee RD, Kang K, Stanich MA, Christiansen J, Wheelock CE, Inman A, Hammock BD, Cornel AJ (2004) Pyrethroid tolerance in Culex pipiens pipiens var. molestus from Marin County, California. Pestic Manag Sci 60:359–368.Google Scholar
  196. Mileson BE, Chambers JE, Chen WL, Dettbarn W, Ehrich M, Eldefrawi AT, Gaylor DW, Hamernik K, Hodgson E, Karczmar AG, Padilla S, Pope CN, Richardson RJ, Saunders DR, Sheets LP, Sultatos LG, Wallace KB (1998) Common mechanism of toxicity: a case study of organophosphorus pesticides. Toxicol Sci 41:8–20.Google Scholar
  197. Moore A, Waring CP (2001) The effects of a synthetic pyrethroid pesticide on some aspects of reproductions in Atlantic salmon (Salmo salar L.). Aquat Toxicol 52:1–12.Google Scholar
  198. Morisseau C, Hammock BD (2005) Epoxide hydrolases: mechanisms, inhibitor designs, and biological roles. Annu Rev Pharmacol Toxicol 45:311–333.Google Scholar
  199. MPSL (2006a) Toxicity Identification results: Region 5: DPCCR (541STC533) and WWNCR (541STC029), Surface Water Ambient Monitoring Program. Prepared by the University of California, Davis, for the Central Valley Regional Water Quality Control Board, Sacramento, CA.Google Scholar
  200. MPSL (2006b) Toxicity Identification Evaluation Results: Region 5: Grayson Drain—541STC030, Surface Water Ambient Monitoring Program. Prepared by the University of California, Davis, for the Central Valley Regional Water Quality Control Board, Sacramento, CA.Google Scholar
  201. Myers M, Richmond RC, Oakeshott JG (1988) On the origins of esterases. Mol Biol Evol 5:113–119.Google Scholar
  202. Narahashi T (1996) Neuronal ion channels as the target sites of insecticides. Pharmacol Toxicol 79:1–14.Google Scholar
  203. Newcomb RD, Campbell PM, Ollis DL, Cheah E, Russell RJ, Oakeshott JG (1997) A single amino acid substitution converts a carboxylesterase to an organophosphorus hydrolase and confers insecticide resistance on a blowfly. Proc Natl Acad Sci U S A 94:7464–7468.Google Scholar
  204. Newman JW, Morisseau C, Hammock BD (2005) Epoxide hydrolases: their roles and interactions with lipid metabolism. Prog Lipid Res 44:1–51.Google Scholar
  205. Oakeshott JG, Claudianos C, Russell RJ, Robin GC (1999) Carboxyl/cholinesterases: a case study of the evolution of a successful multigene family. BioEssays 21:1031–1042.Google Scholar
  206. Oakeshott JG, Devonshire AL, Claudianos C, Sutherland TD, Horne I, Campbell PM, Ollis DL, Russell RJ (2005) Comparing the organophosphorus and carbamate insecticide resistance mutations in cholin- and carboxyl-esterases. Chem Biol Interact 157–158:269–275.Google Scholar
  207. O’Connor TP (2002) National distribution of chemical concentrations in mussels and oysters in the USA. Mar Environ Res 53:117–143.Google Scholar
  208. Ohno N, Fujimoto K, Okuno Y, Mizutani T, Hirano M, Itaya N, Honda T, Yoshioka H (1976) 2-Arylalkanoates, a new group of synthetic pyrethroid esters not containing cyclopropanecarboxylates. Pestic Sci 7:241–246.Google Scholar
  209. Ollis DL, Cheah E, Cygler M, Dijkstra B, Frolow F, Franken SM, Harel M, Remington SJ, Silman I, Schrag J, Sussman JL, Verschueren KHG, Goldman A (1992) The α/β hydrolase fold. Protein Eng 5:197–211.Google Scholar
  210. O’Malley M (1997) Clinical evaluation of pesticide exposure and poisonings. Lancet 349:1161–1166.Google Scholar
  211. O’Neill AJ, Galloway TS, Browne MA, Dissanayake A, Depledge MH (2004) Evaluation of toxicity in tributaries of the Mersey estuary using the isopod Asellus aquaticus (L.). Mar Environ Res 58:327–331.Google Scholar
  212. Oros D, Werner I (2005) Pyrethroid Insecticides: An Analysis of Use Patterns, Distributions, Potential Toxicity and Fate in the Sacramento-San Joaquin Delta and Central Valley. White Paper for the Interagency Ecological Program. SFEI Contribution 415. San Francisco Estuary Institute, Oakland, CA.Google Scholar
  213. Ozretic B, Krajnovic-Ozretic M (1992) Esterase heterogeneity in mussel Mytilus galloprovincialis: effects of organophosphate and carbamate pesticides in vitro. Comp Biochem Physiol C 103:221–225.Google Scholar
  214. Pap L (2003) Pyrethroids. In: Plimmer JR, Gammon DW, Ragsdale NN (eds) Encyclopedia of Agrochemicals. Wiley, New York.
  215. Parker ML, Goldstein MI (2000) Differential toxicities of organophosphate and carbamate insecticides in the nestling European starling (Sturnus vulgaris). Arch Environ Contam Toxicol 39:233–242.Google Scholar
  216. Pathiratne A, George SG (1998) Toxicity of malathion to Nile tilapia, Oreochromis niloticus and modulation by other environmental contaminants. Aquat Toxicol 43:261–271.Google Scholar
  217. Phillips BM, Anderson BS, Hunt JW, Nicely PA, Kosaka RA, Tjeerdema RS, de Vlaming V, Richard N (2004) In situ water and sediment toxicity in an agricultural watershed. Environ Toxicol Chem 23:435–442.Google Scholar
  218. Phillips BM, Anderson BA, Hunt JW, Huntley SA, Tjeerdema RS, Richard N, Worcester K (2006) Solid-phase sediment Toxicity Identification Evaluation in an agricultural stream. Environ Toxicol Chem 25:1671–1676.Google Scholar
  219. Phillips BM, Anderson BS, Hunt JW, Tjeerdema RS, Carpio-Obeso M, Connor V (2007) Causes of water column toxicity to Hyalella azteca in the New River, California USA. Environ Toxicol Chem 26:1074–1079.Google Scholar
  220. Pindel EV, Kedishvili NY, Abraham TL, Brzezinski MR, Zhang J, Dean RA, Borson WF (1997) Purification and cloning of a broad substrate specificity human liver carboxylesterase that catalyzes the hydrolysis of cocaine and heroin. J Biol Chem 272:14769–14775.Google Scholar
  221. Potter PM, Wadkins RM (2006) Carboxylesterases: detoxifying enzymes and targets for drug therapy. Curr Med Chem 13:1045–1054.Google Scholar
  222. Potter PM, Pawlik CA, Morton CL, Naeve CW, Danks MK (1998) Isolation and partial characterization of a cDNA encoding a rabbit liver carboxylesterase that activates the prodrug irinotecan (CPT-11). Cancer Res 58:2646–2651.Google Scholar
  223. Quinn DM (1987) Acetylcholinesterase: enzyme structure, reaction dynamics, and virtual transition states. Chem Rev 87:955–979.Google Scholar
  224. Quinn DM (1997) Esterases of the α/β hydrolase fold family. In: Guengerich F (ed) Biotransformation. Elsevier, Oxford, pp 243–264.Google Scholar
  225. Quinn DM (1999) Ester hydrolysis. In: Poulter C (ed) Enzymes, Enzyme Mechanisms, Proteins, and Aspects of NO Chemistry. Elsevier, Oxford, pp 101–137.Google Scholar
  226. Ray DE, Forshaw PJ (2000) Pyrethroid insecticides: poisoning syndromes, synergies, and therapy. J Toxicol Clin Toxicol 38:95–101.Google Scholar
  227. Redinbo MR, Potter PM (2005) Mammalian carboxylesterases: from drug targets to protein therapeutics. Drug Discov Today 10:313–325.Google Scholar
  228. Redinbo MR, Bencharit S, Potter PM (2003) Human carboxylesterase. 1: From drug metabolism to drug discovery. Biochem Soc Trans 31:620–624.Google Scholar
  229. Regel RH, Ferris JM, Ganf GG, Brookes JD (2002) Algal esterase activity as a biomeasure of environmental degradation in a freshwater creek. Aquat Toxicol 59:209–223.Google Scholar
  230. Rickwood CJ, Galloway TS (2004) Acetylcholinesterase inhibition as a biomarker of adverse effect. A study of Mytilus edulis exposed to the priority pollutant chlorfenvinphos. Aquat Toxicol 67:45–56.Google Scholar
  231. Riddles PW, Schnitzerling HJ, Davey PA (1983) Application of trans and cis isomers of p-nitrophenyl-(1R, S)-3-(2, 2-dichlorovinyl)-2, 2-dimethylcyclopropanecarboxylate to the assay of pyrethroid hydrolyzing esterases. Anal Biochem 132:105–109.Google Scholar
  232. Rosa E, Barata C, Damasio J, Bosch MP, Guerrero A (2006) Aquatic ecotoxicity of a pheromonal antagonist in Daphnia magna and Desmodesmus subspicatus. Aquat Toxicol 79:296–303.Google Scholar
  233. Roy C, Grolleau G, Chamoulaud S, Riviere JL (2005) Plasma B-esterase activities in European raptors. J Wildl Dis 41:184–208.Google Scholar
  234. Sanchez JC, Fossi MC, Focardi S (1997a) Serum “B” esterases as a nondestructive biomarker for monitoring the exposure of reptiles to organophosphorus insecticides. Ecotoxicol Environ Saf 38:45–52.Google Scholar
  235. Sanchez JC, Fossi MC, Focardi S (1997b) Serum B esterases as a nondestructive biomarker in the lizard Gallotia galloti experimentally treated with parathion. Environ Toxicol Chem 16:1954–1961.Google Scholar
  236. Sanchez-Hernandez JC (2006) Earthworm biomarkers in ecological risk assessment. Rev Environ Contam Toxicol 188:85–126.Google Scholar
  237. Sanchez-Hernandez JC, Fossi MC, Leonzio C, Focardi S (1998) Use of biochemical biomarkers as a screening tool to focus the chemical monitoring of organic pollutants in the Biobio River basin (Chile). Chemosphere 37:699–710.Google Scholar
  238. Sarkar A, Ray D, Shrivastava AN, Sarker S (2006) Molecular biomarkers: their significance and application in marine pollution monitoring. Ecotoxicology 15:333–340.Google Scholar
  239. Satoh T, Hosokawa M (1995) Molecular aspects of carboxylesterase isoforms in comparison with other esterases. Toxicol Lett 82–83:439–445.Google Scholar
  240. Satoh T, Hosokawa M (1998) The mammalian carboxylesterases: from molecules to functions. Annu Rev Pharmacol Toxicol 38:257–288.Google Scholar
  241. Satoh T, Hosokawa M (2000) Organophosphates and their impact on the global environment. Neurotoxicology 21:223–227.Google Scholar
  242. Satoh T, Hosokawa M (2006) Structure, function and regulation of carboxylesterases. Chem Biol Interact 162:195–211.Google Scholar
  243. Satoh T, Taylor P, Borsron WF, Sanghani SP, Hosokawa M, La Du BN (2002) Current progress on esterases: from molecular structure to function. Drug Metab Dispos 30:488–493.Google Scholar
  244. Schechter MS, Green N, LaForge FB (1949) Constituents of pyrethrum flowers. XXIII. Cinerolone and the synthesis of related cyclopentenolones. J Am Chem Soc 71:3165–3173.Google Scholar
  245. Schulz R (2004) Field studies on exposure, effects, and risk mitigation of aquatic nonpoint-source insecticide pollution: a review. J Environ Qual 33:419–448.Google Scholar
  246. Shan G, Stoutamire DW, Wengatz I, Gee SJ,. Hammock BD (1999) Development of an immunoassay for the pyrethroid insecticide esfenvalerate J Agric Food Chem 47:2145–2155.Google Scholar
  247. Shan G, Leeman WR, Stoutamire DW, Gee SJ, Chang DPY, Hammock BD (2000) Enzyme-linked immunosorbent assay for the pyrethroid permethrin J Agric Food Chem 48:4032–4040.Google Scholar
  248. Sharom MS, Solomon KR (1981) Adsorption and desorption of permethrin and other pesticides on glass and plastic materials used in bioassay procedures. Can J Fish Aquat Sci 38:199–204.Google Scholar
  249. Sheets LP, Doherty JD, Law MW, Reiter LW, Crofton KM (1994) Age-dependent differences in the susceptibility of rats to deltamethrin. Toxicol Appl Pharmacol 126:186–190.Google Scholar
  250. Shi D, Yang J, Yang D, LeCluyse EL, Black C, You L, Akhlaghi F, Yan B (2006) Anti-influenza prodrug oseltamivir is activated by carboxylesterase human carboxylesterase 1, and the activation is inhibited by antiplatelet agent clopidogrel. J Pharmacol Exp Ther 319:1477–1484.Google Scholar
  251. Simpson SL, Micevska T, Adams MS, Stone A, Maher WA (2007) Establishing cause-effect relationships in hydrocarbon-contaminated sediments using a sublethal response of the benthic marine alga, Entomoneis cf. punctulata. Environ Toxicol Chem 26:163–170.Google Scholar
  252. Singh BK, Walker A (2006) Microbial degradation of organophosphorus compounds. FEMS Microbiol Rev 30:428–471.Google Scholar
  253. Soderlund DM, Casida JE (1977) Stereospecificity of pyrethroid metabolism in mammals. In: Elliot M (ed) Synthetic Pyrethroids. American Chemical Society, Washington, DC, pp 173–185.Google Scholar
  254. Sogorb MA, Vilanova E (2002) Enzymes involved in the detoxification of organophosphorus, carbamate and pyrethroid insecticides through hydrolysis. Toxicol Let 128:215–228.Google Scholar
  255. Sogorb MA, Vilanova E, Carrera V (2004) Future applications of phosphotriesterases in the prophylaxis and treatment of organophosporus insecticide and nerve agent poisonings. Toxicol Lett 151:219–233.Google Scholar
  256. Solomon MG, Fitzgerald JD (1993) Orchard selection for resistance to a synthetic pyrethroid in organophosphate-resistant Typhlodromus-Pyri in the UK. Biocontrol Sci Technol 3:127–132.Google Scholar
  257. Spurlock F, Bacey J, Starner K, Gill S (2005) A probabilistic screening model for evaluating pyrethroid surface water monitoring data. Environ Monit Assess 109:161–179.Google Scholar
  258. Staudinger H, Ruzicka L (1924) Insektentotende stoffe. I-VI and VIII-X. Helv Chim Acta 7:177–458.Google Scholar
  259. Stok J, Huang H, Jones PJ, Wheelock CE, Morisseau C, Hammock BD (2004a) Identification, expression and purification of a pyrethroid hydrolyzing carboxylesterase from mouse liver microsomes. J Biol Chem 279:29863–29869.Google Scholar
  260. Stok JE, Goloshchapov A, Song C, Wheelock CE, Derbel MB, Morisseau C, Hammock BD (2004b) Investigation of the role of a second conserved serine in carboxylesterases via site-directed mutagenesis. Arch Biochem Biophys 430:247–255.Google Scholar
  261. Straus DL, Chambers JE (1995) Inhibition of acetylcholinesterase and aliesterases of fingerling channel catfish by chlorpyrifos, parathion, and S,S,S,-tributyl phosphorotrithioate (DEF). Aquat Toxicol 33:311–324.Google Scholar
  262. Sturm A, Wogram J, Segner H, Liess M (2000) Different sensitivity to organophosphates of acetylcholinesterase and butylcholinesterase from three-spined stickleback (Gasterosteus aculeatus) application in biomonitoring. Environ Toxicol Chem 19:1607–1615.Google Scholar
  263. Sutherland TD, Weir KM, Lacey MJ, Horne I, Russell RJ, Oakeshott JG (2002) Enrichment of a microbial culture capable of degrading endosulphate, the toxic metabolite of endosulfan. J Appl Microbiol 92:541–548.Google Scholar
  264. Sutherland TD, Horne I, Weir KM, Coppin CW, Williams MR, Selleck M, Russell RJ, Oakeshott JG (2004) Enzymatic bioremediation: from enzyme discovery to applications. Clin Exp Pharmacol Physiol 31:817–821.Google Scholar
  265. Sweeney RE, Maxwell DM (1999) A theoretical model of the competition between hydrolase and carboxylesterase in protection against organophosphorus poisoning. Math Biosci 160:175–190.Google Scholar
  266. Székács A, Bordás B, Hammock BD (1992) Transition state analog enzyme inhibitors: structure-activity relationships of trifluoromethyl ketones. In: Draber W, Fujita T (eds) Rational Approaches to Structure, Activity, and Ecotoxicology of Agrochemicals. CRC Press, Boca Raton, FL, pp 219–249.Google Scholar
  267. Talcott RE (1979) Hepatic and extrahepatic malathion carboxylesterases. Assay and localization in the rat. Toxicol Appl Pharmacol 47:145–150.Google Scholar
  268. Talcott RE, Denk H, Mallipudi NM (1979a) Malathion carboxylesterase activity in human liver and its inactivation by isomalathion. Toxicol Appl Pharmacol 49:373–376.Google Scholar
  269. Talcott RE, Mallipudi NM, Fukuto TR (1979b) Malathion carboxylesterase titer and its relationship to malathion toxicity. Toxicol Appl Pharmacol 50:501–504.Google Scholar
  270. Talcott RE, Mallipudi NM, Umetsu N, Fukuto TR (1979c) Inactivation of esterases by impurities isolated from technical malathion. Toxicol Appl Pharmacol 49:107–112.Google Scholar
  271. Tang BK, Kalow W (1995) Variable activation of lovastatin by hydrolytic enzymes in human plasma and liver. J Clin Pharmacol 47:449–451.Google Scholar
  272. TDC (2003) Insecticide Market Trends and Potential Water Quality Implications. San Francisco Estuary Project, San Mateo, CA.Google Scholar
  273. Teh SJ, Deng D, Werner I, Teh F, Hung SS (2005) Sublethal toxicity of orchard stormwater runoff in Sacramento splittail (Pogonichthys macrolepidotus) larvae. Mar Environ Res 59:203–216.Google Scholar
  274. Thompson HM (1993) Avian serum esterases: species and temporal variations and their possible consequences. Chem-Biol Interact 87:329–338.Google Scholar
  275. Thompson HM (1999) Esterases as markers of exposure to organophosphates and carbamates. Ecotoxicology 8:369–384.Google Scholar
  276. Thompson HM, Mackness MI, Walker CH, Hardy AR (1991a) Species differences in avian serum B esterases revealed by chromatofocusing and possible relationships of esterase activity to pesticide toxicity. Biochem Pharmacol 41:1235–1240.Google Scholar
  277. Thompson HM, Walker CH, Hardy AR (1991b) Changes in activity of avian serum esterases following exposure to organophosphorus insecticides. Arch Environ Contam Toxicol 20:514–518.Google Scholar
  278. Tippe A (1993) Are pyrethroids harmless? Evaluation of experimental data. Zentralbl Hyg Umweltmed 194:342–359.Google Scholar
  279. Tyler CR, Beresford N, van der Woning M, Sumpter JP, Thorpe K (2000) Metabolism and environmental degradation of pyrethroid insecticides produce compounds with endocrine activities. Environ Toxicol Chem 19:801–809.Google Scholar
  280. USEPA (1991) Methods for aquatic toxicity identification evaluations. Phase I Toxicity Characterization Procedures. EPA 600/6–91/003. Office of Research and Development, U.S. Environmental Protection Agency, Washington, DC.Google Scholar
  281. USEPA (1992) Toxicity identification evaluation: characterization of chronically toxic effluents, phase I. EPA-600/6–91/005F. Office of Research and Development, USEPA, Duluth, MN.Google Scholar
  282. USEPA (1993a) Methods for aquatic toxicity identification evaluations. Phase III Confirmation Procedures for Samples Exhibiting Acute and Chronic Toxicity. EPA 600/R-92/081. Office of Research and Development, USEPA, Washington, D.C.Google Scholar
  283. USEPA (1993b) Methods for aquatic toxicity identification evaluations. Phase II Toxicity Identification Procedures for Samples Exhibiting Acute and Chronic Toxicity. EPA 600/R-92/080. Office of Research and Development, USEPA, Washington, DC.Google Scholar
  284. USEPA (1996) Marine Toxicity Identification Evaluation (TIE): Phase I Guidance Document. EPA/600/R-95/054. Office of Research and Development, USEPA, Washington, DC.Google Scholar
  285. USEPA (2002) Methods for measuring acute toxicity of effluents and receiving water to freshwater and marine organisms. EPA-821-R-02–021. Office of Research and Development, USEPA, Washington, DC.Google Scholar
  286. USEPA (2004) Incidence and severity of sediment contamination in surface waters of the United States. National Sediment Quality Survey, 2nd Ed. EPA-823-R-04–007. Office of Science and Technology, Standards and Health Protection Division, USEPA, Washington, DC.Google Scholar
  287. USEPA (2007) Sediment Toxicity Identification Evaluation (TIE) Phases I, II, and III Guidance Document. EPA 600/R-07/080. Office of Research and Development, Washington, DC.Google Scholar
  288. Vijverberg HP, van den Bercken J (1990) Neurotoxicological effects and the mode of action of pyrethroid insecticides. Crit Rev Toxicol 21:105–126.Google Scholar
  289. Vioque-Fernandez A, de Almeida EA, Ballesteros J, Garcia-Barrera T, Gomez-Ariza JL, Lopez-Barea J (2007a) Donana National Park survey using crayfish (Procambarus clarkii) as bioindicator: esterase inhibition and pollutant levels. Toxicol Lett 168:260–268.Google Scholar
  290. Vioque-Fernandez A, de Almeida EA, Lopez-Barea J (2007b) Esterases as pesticide biomarkers in crayfish (Procambarus clarkii, Crustacea): tissue distribution, sensitivity to model compounds and recovery from inactivation. Comp Biochem Physiol C 145:404–412.Google Scholar
  291. Wadkins RM, Morton CL, Weeks JK, Oliver L, Wierdl M, Danks MK, Potter PM (2001) Structural constraints affect the metabolism of 7-ethyl-10-[4-(1-piperidino)-1-piperidino]carbonyloxycamptothecin (CPT-11) by carboxylesterases. Mol Pharmacol 60:355–362.Google Scholar
  292. Wadkins RM, Hyatt JL, Yoon KJ, Morton CL, Lee RE, Damodaran K, Beroza P, Danks MK, Potter PM (2004) Discovery of novel selective inhibitors of human intestinal carboxylesterase for the amelioration of irinotecan-induced diarrhea: synthesis, quantitative structure-activity relationship analysis, and biological activity. Mol Pharmacol 65:1336–1343.Google Scholar
  293. Wadkins RM, Hyatt JL, Wei X, Yoon KJ, Wierdl M, Edwards CC, Morton CL, Obenauer JC, Damodaran K, Beroza P, Danks MK, Potter PM (2005) Identification and characterization of novel benzil (diphenylethane-1, 2-dione) analogues as inhibitors of mammalian carboxylesterases. J Med Chem 48:2906–2915.Google Scholar
  294. Wagner JM (1997) Food Quality Protection Act: its impact on the pesticide industry. Qual Assur 5:279–283.Google Scholar
  295. Waller WT, Bailey HA, de Vlaming V, Ho KT, Hunt JW, Miller JL, Pillard DA, Rowland CD, Venables BJ (2005) Ambient water, interstitial water, and sediment. Society of Environmental Toxicology and Chemistry Press, Pensacola, FL, pp 93–114.Google Scholar
  296. Ware GW, Whitacre DM (2004) The Pesticide Book, 6th Ed. Meister, Willoughby, OH.Google Scholar
  297. Watanabe T, Shan G, Stoutamire DW, Gee SJ, Hammock BD (2001) Development of a class-specific immunoassay for the type I pyrethroid insecticides. Anal Chim Acta 444:119–129.Google Scholar
  298. Wengatz I, Stoutamire DW, Gee SJ, Hammock BD (1998) Development of an enzyme-linked immunosorbent assay for the detection of the pyrethroid insecticide fenpropathrin. J Agric Food Chem 46:2211–2221.Google Scholar
  299. Werner I, Deanovic LA, Connor V, de Vlaming V, Bailey HC, Hinton DE (2000) Insecticide-caused toxicity to Ceriodaphnia dubia (Cladocera) in the Sacramento-San Joaquin River Delta, California, USA. Environ Toxicol Chem 19:215–227.Google Scholar
  300. Werner I, Deanovic LA, Hinton DE, Henderson JD, de Oliveira GH, Wilson BW, Krueger W, Wallender WW, Oliver MN, Zalom FG (2002) Toxicity of stormwater runoff after dormant spray application of diazinon and esfenvalerate (Asana) in a French prune orchard, Glenn county, California, USA. Bull Environ Contam Toxicol 68:29–36.Google Scholar
  301. Werner I, Zalom FG, Oliver MN, Deanovic LA, Kimball TS, Henderson JD, Wilson BW, Krueger W, Wallender WW (2004) Toxicity of storm-water runoff after dormant spray application in a french prune orchard, Glenn County, California, USA: temporal patterns and the effect of ground covers. Environ Toxicol Chem 23:2719–2726.Google Scholar
  302. West CW, Kosian PA, Mount DR, Makynen EA, Pasha MS, Sibley PK, Ankley GT (2001) Amendment of sediments with a carbonaceous resin reduces bioavailability of polycyclic aromatic hydrocarbons. Environ Toxicol Chem 20:1104–1111.Google Scholar
  303. Weston D (2006) Temperature Dependence of Pyrethroid Toxicity: TIE Applications and Environmental Consequences. Society of Environmental Toxicological Chemistry, Montreal, Canada.Google Scholar
  304. Weston DP, Amweg EL (2007) Whole sediment toxicity identification evaluation tools for pyrethroid insecticides: II. Esterase addition. Environ Toxicol Chem 26:2397–2404.Google Scholar
  305. Weston DP, You J, Lydy MJ (2004) Distribution and toxicity of sediment-associated pesticides in the agriculture-dominated water bodies of California’s Central Valley. Environ Sci Technol 38:2752–2759.Google Scholar
  306. Weston DP, Holmes RW, You J, Lydy MJ (2005) Aquatic toxicity due to residential use of pyrethroid insecticides. Environ Sci Technol 39:9778–9784.Google Scholar
  307. Wheelock CE, Severson TF, Hammock BD (2001) Synthesis of new carboxylesterase inhibitors and evaluation of potency and water solubility. Chem Res Toxicol 14:1563–1572.Google Scholar
  308. Wheelock CE, Colvin ME, Uemura I, Olmstead MM, Nakagawa Y, Sanborn JR, Jones AD, Hammock BD (2002) Use of ab initio calculations to predict esterase inhibitor potency. J Med Chem 45:5576–5593.Google Scholar
  309. Wheelock CE, Wheelock ÅM, Zhang R, Stok JE, Le Valley SE, Green CE, Hammock BD (2003) Evaluation of α-cyanoesters as fluorescent substrates for examining interindividual variation in general and pyrethroid-selective esterases in human liver microsomes. Anal Biochem 315:208–222.Google Scholar
  310. Wheelock CE, Miller JL, Miller MG, Shan G, Gee SJ, Hammock BD (2004) Development of Toxicity Identification Evaluation (TIE) procedures for pyrethroid detection using esterase activity. Environ Toxicol Chem 23:2699–2708.Google Scholar
  311. Wheelock CE, Eder KJ, Werner I, Huang H, Jones PD, Brammell BF, Elskus AA, Hammock BD (2005a) Individual variability in esterase activity and CYP1A levels in Chinook salmon (Oncorhynchus tshawytscha) exposed to esfenvalerate and chlorpyrifos. Aquat Toxicol 74:172–192.Google Scholar
  312. Wheelock CE, Miller JL, Miller MJ, Phillips BM, Gee SJ, Tjeerdema RS, Hammock BD (2005b) Influence of container adsorption upon observed pyrethroid toxicity to Ceriodaphnia dubia and Hyalella azteca. Aquat Toxicol 74:47–52.Google Scholar
  313. Wheelock CE, Shan G, Ottea JA (2005c) Overview of carboxylesterases and their role in metabolism of insecticides. J Pestic Sci 30:75–83.Google Scholar
  314. Wheelock CE, Miller JL, Miller MJ, Phillips BM, Huntley SA, Gee SJ, Tjeerdema RS, Hammock BD (2006) Use of carboxylesterase activity to remove pyrethroid-associated toxicity to Ceriodaphnia dubia and Hyalella azteca in toxicity identification evaluations. Environ Toxicol Chem 25:973–984.Google Scholar
  315. Wheelock CE, Nishi K, Ying A, Jones PD, Colvin ME, Olmstead MM, Hammock BD (in press) Influence of sulfur oxidation state and steric bulk upon trifluoromethyl ketone (TFK) binding kinetics to carboxylesterases and fatty acid amide hydrolase (FAAH). Bioorg Med Chem in press.Google Scholar
  316. Williams FM (1985) Clinical significance of esterases in man. Clin Pharmacokinet 10:392–403.Google Scholar
  317. Wilson BW, Henderson JD (1992) Blood esterase determinations as markers of exposure. Rev Environ Contam Toxicol 128:55–69.Google Scholar
  318. Wogram J, Sturm A, Segner H, Liess M (2001) Effects of parathion on acetylcholinesterase, butyrylcholinesterase, and carboxylesterase in three-spined stickleback (Gasterosteus aculeatus) following short-term exposure. Environ Toxicol Chem 20:1528–1531.Google Scholar
  319. Wortberg M., Jones G, Kreissig SB, Rocke DM, Gee SJ, Hammock BD (1996) An approach to the construction of an immunoarray for differentiating and quantitating cross reacting analytes. Anal Chim Acta 319:291–303.Google Scholar
  320. Yamamoto R (1923) The insecticidal principle in Chrysanthemum cinerariaefolium. Part II and part III. On the constitution of pyrethronic acid. J Chem Soc Jpn 44:311–330.Google Scholar
  321. Yamamoto R (1925) On the insecticidal principle of insect powder. Inst Phys Chem Res Tokyo 3:195.Google Scholar
  322. Yang H, Carr PD, McLoughlin SY, Liu JW, Horne I, Qiu X, Jeffries CM, Russell RJ, Oakeshott JG, Ollis DL (2003) Evolution of an organophosphate-degrading enzyme: a comparison of natural and directed evolution. Protein Eng 16:135–145.Google Scholar
  323. Yang WC, Gan JY, Hunter W, Spurlock F (2006a) Effect of suspended solids on bioavailability of pyrethroid insecticides. Environ Toxicol Chem 25:1585–1591.Google Scholar
  324. Yang WC, Spurlock F, Liu WP, Gan JY (2006b) Effects of dissolved organic matter on permethrin bioavailability to Daphnia species. J Agric Food Chem 54:3967–3972.Google Scholar
  325. Yang WC, Spurlock F, Liu WP, Gan JY (2006c) Inhibition of aquatic toxicity of pyrethroid insecticides by suspended sediment. Environ Toxicol Chem 25:1913–1919.Google Scholar
  326. Yang ZP, Dettbarn WD (1998) Prevention of tolerance to the organophosphorus anticholinesterase paraoxon with carboxylesterase inhibitors. Biochem Pharmacol 55:1419–1426.Google Scholar
  327. Zhang J, Burnell JC, Dumaual N, Bosron WF (1999) Binding and hydrolysis of meperidine by human liver carboxylesterase hCE-1. J Pharmacol Exp Ther 290:314–318.Google Scholar
  328. Zhao GY, Rose RL, Hodgson E, Roe RM (1996) Biochemical mechanisms and diagnostic microassays for pyrethroid, carbamate, and organophosphate insecticide resistance/cross-resistance in the tobacco budworm, Heliothis virescens. Pestic Biochem Phys 56:183–195.Google Scholar

Copyright information

© Springer 2008

Authors and Affiliations

  • Craig E. Wheelock
    • 1
  • Bryn M. Phillips
    • 2
  • Brian S. Anderson
    • 2
  • Jeff L. Miller
    • 3
  • Mike J. Miller
    • 3
  • Bruce D. Hammock
    • 4
  1. 1.Division of Physiological Chemistry II, Department of Medical Biochemistry and BiophysicsKarolinska InstitutetStockholmSweden
  2. 2.Department of Environmental ToxicologyUniversity of California Davis, Marine Pollution Studies LaboratoryMontereyUSA
  3. 3.AQUA-Science, Inc.DavisUSA
  4. 4.Department of EntomologyUniversity of California DavisDavisUSA

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