Skip to main content

Persistent Polyhalogenated Compounds: Biochemistry, Toxicology, Medical Applications, and Associated Environmental Issues

  • Chapter
Biochemistry of the Elemental Halogens and Inorganic Halides

Part of the book series: Biochemistry of the Elements ((BOTE,volume 9A+B))

Abstract

This chapter will focus on several classes of halogenated compounds that have had widespread practical applications in industry and commerce. Because many of these compounds are chemically and thermally very stable, their extensive use has evoked serious concerns over potential longterm harmful effects to the environment. Indeed, many of these compounds have proven to be quite toxic, and environmental concerns are increased by their bioaccumulation in the food chain. Research designed to elucidate mechanisms of toxicity has helped define environmental issues and has produced significant biochemical data not only on the toxicology of the compounds of concern, but also on cellular mechanisms of the organisms involved, including humans. The environmental impact of certain halogenated compounds makes this topic a matter of extreme relevance, and inclusion of this subject in this volume clearly is appropriate. Biochemistry, toxicity, and potential environmental impact of several classes of halogenated insecticides will be considered first. This will be followed by a review of the problems associated with the toxicity of polyhalogenated hydrocarbons and related phenols, dioxins, and dibenzofurans. The development of halogenated volatile anesthetics and the use of perfluorinated aliphatic hydrocarbons as artificial oxygen carriers will be reviewed briefly. The biochemistry of simple halogenated aliphatic compounds, such as chloroform and carbon tetrachloride, is related in large part to metabolic activation to toxic species and will be discussed in Chapter 9.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Ali, S. F., Hong, J.-S., Wilson, J. E., Lamb, J. C., Moore, J. A., Mason, G. A., and Bondy, S. C., 1982. Subchronic dietary exposure of rats to chlordecone (KeponeR) modifies levels of hypothalamic ß-endorphine, Neurotoxicology 3: 119–124.

    PubMed  CAS  Google Scholar 

  • Bastomsky, C. H., 1977. Enhanced thyroxine metabolism and high uptake goiters in rats after a single dose of 2,3,7,8-tetrachloro-p-dioxin, Endocrinology 101: 292–296.

    PubMed  CAS  Google Scholar 

  • Bickel, M. H., and Muehlebach, S., 1980. Pharmacokinetics and ecodisposition of polyhalogenated hydrocarbons: Aspects and concepts, Drug Metab. Rev. 11: 149–190.

    PubMed  CAS  Google Scholar 

  • Birnbaum, L. S., Weber, H., Harris, M. W., Lamb, J. C., IV, and McKinney, J. D., 1985. Toxic interaction of specific polychlorinated biphenyls and 2,3,7,8-tetrachlorodibenzo-pdioxin: Increased incidence of cleft palate in mice, Toxicol. Appl. Pharmacol. 77: 292–302.

    PubMed  CAS  Google Scholar 

  • Bloomquist, J. R., and Soderlund, D. M., 1985. Neurotoxic insecticides inhibit GABAdependent chloride uptake by mouse brain vesicles, Biochem. Biophys. Res. Commun. 133: 37–43.

    PubMed  CAS  Google Scholar 

  • Bloomquist, J. R., Adams, P. M., and Soderlund, D. M., 1986. Inhibition of y-aminobutyric acid-stimulated chloride flux in mouse brain vesicles by polychlorocycloalkane and pyrethroid insecticides, Neurotoxicology 7: 11–20.

    PubMed  CAS  Google Scholar 

  • Bondy, S. C., and Hong, J. S., 1987. Modulation of adrenal ornithine decarboxylase by chlordecone, p, p’-DDT and permethrin, Neurotoxicology 8: 15–22.

    PubMed  CAS  Google Scholar 

  • Brinkman, U. A. Th., ad De Kok, A., 1980. Production, properties and usage, in Halogenated Biphenyls, Terphenyls, Naphthalenes, Dibenzodioxins and Related Products ( R. D. Kimbrough, ed.), Elsevier/North-Holland Biomedical Press, Amsterdam, pp. 1–40.

    Google Scholar 

  • Brooks, G. T., 1986. Insecticide metabolism and selective toxicity, Xenobiotica 16: 989–1002.

    PubMed  CAS  Google Scholar 

  • Chae, K., and McKinney, J. D., 1988. Molecular complexes of thyroid hormone tyrosyl rings with aromatic donors. Possible relationship to receptor protein interactions, J. Med. Chem. 31: 357–362.

    PubMed  CAS  Google Scholar 

  • Chen, P. H., Tilson, H. A., Marbury, G. D., Karboum, F., and Hong, J. S., 1985. Effect of chlordecone (Kepone) on the rat brain concentration of 3-methoxy-4-hydroxyphenyl glycol: Evidence for a possible involvement of the norepinephrine system in chlordeconeinduced tremor, Toxicol. Appl. Pharmacol. 77: 158–164.

    PubMed  CAS  Google Scholar 

  • Christ, D. D., Satoh, H., Kenna, J. G., and Pohl, L. R., 1988. Potential metabolic basis for enflurane hepatitis and the apparent cross-sensitization between enflurane and halothane, Drug Metab. Dispos. 16: 135–140.

    PubMed  CAS  Google Scholar 

  • Clark, L. C., Jr., and Gollan, F., 1966. Survival of mammals breathing organic liquids equilibrated with oxygen at atmospheric pressure, Science 152: 1755–1756.

    PubMed  CAS  Google Scholar 

  • Clark, L. C., Jr., and Moore, R. E., 1982. Basic and experimental aspects of oxygen transport by highly fluorinated organic compounds, in Biomedicinal Aspects of Fluorine Chemistry ( R. Filler and Y. Kobayashi, eds.), Kodansha Ltd., Tokyo, and Elsevier Biomedical Press, Amsterdam, pp. 213–226.

    Google Scholar 

  • Clark, L. C., Jr., Wesseler, E. P., Kaplan, S., Emory, C., Moore, R., and Denson, D., 1976. Intravenous infusion of cis-trans perfluorodecalin emulsions in the Rhesus monkey, in Biochemistry Involving Carbon-Fluorine Bonds (R. Filler, ed.), ACS Symposium Series 28, American Chemical Society, Washington, D.C., pp. 135–170.

    Google Scholar 

  • Coats, J. R., Metcalf, R. L., and Kapoor, I. P., 1977. Effective DDT analogues with altered aliphatic moieties. Isobutanes and chloropropanes, J. Agric. Food Chem. 25: 859–868.

    PubMed  CAS  Google Scholar 

  • Cole, L. M., and Casida, J. E., 1986. Polychlorocycloalkane insecticide-induced convulsions in mice in relation to disruption of the GABA-regulated chloride ionophore, Life Sci. 39: 1855–1862.

    PubMed  CAS  Google Scholar 

  • Costa, L. G., 1987a. Toxicology of pesticides: a brief history, in Toxicology of Pesticides: Experimental, Clinical and Regulatory Perspectives ( L. G. Costa, C. L. Galli, and S. D. Murphy, eds.), Spinger-Verlag, Berlin, pp. 1–10.

    Google Scholar 

  • Costa, L. G., 1987b. Interaction of insecticides with the nervous system, in Toxicology of Pesticides: Experimental, Clinical and Regulatory Perspectives ( L. G. Costa, C. L. Galli, and S. D. Murphy, eds.), Springer-Verlag, Berlin, pp. 77–91.

    Google Scholar 

  • Denson, D. D., Uyeno, E. T., Simon, R. L., Jr., and Peters, H. M., 1976. Preparation and physiological evaluation of some new fluorinated volatile anesthetics, in Biochemistry Involving Carbon-Fluorine Bonds (R. Filler, ed.), ACS Symposium Series 28, American Chemical Society, Washington, D.C., pp. 190–208.

    Google Scholar 

  • Desaiah, D.,1982. Biochemical mechanisms of chlordecone neurotoxicity: A review, Neurotoxicology 3: 103–110.

    Google Scholar 

  • Dobkin, A. B., 1979a. Anesthetic history, in Development of New Volatile Inhalation Anaesthetics (A. B. Dobkin, ed. ), Elsevier/North-Holland Press, pp. 1–4.

    Google Scholar 

  • Dobkin, A. B., 1979b. Enflurane (Ethrane), in Development of New Volatile Inhalation Anaesthetics ( A. B. Dobkin, ed.), Elsevier/North-Holland Press, Amsterdam, pp. 155–228.

    Google Scholar 

  • Dobkin, A. B., 1979c. Forane (isoflurane, compound 469), in Development of New Volatile Inhalation Anaesthetics (A. B. Dobkin, ed. ), Elsevier/North-Holland Press, pp. 229–264.

    Google Scholar 

  • Dubois, J. M., and Bergman, C., 1977. Asymmetrical currents and sodium currents in Ranvier nodes exposed to DDT, Nature 266: 741–742.

    PubMed  CAS  Google Scholar 

  • Evers, A. S., Berkowitz, B. A., and d’Avignon, D. A., 1987. Correlation between the anaesthetic effect of halothane and saturable binding in brain, Nature 328: 157–160.

    PubMed  CAS  Google Scholar 

  • Evers, A. S., Haycock, J. C., and d’Avignon, D. A., 1988. The potency of fluorinated ether anesthetics correlates with their 19F spin-spin relaxation times in brain tissue, Biochem. Biophys. Res. Commun. 151: 1039–1045.

    PubMed  CAS  Google Scholar 

  • Faithfull, N. S., 1987. Fluorocarbons, current status and future applications, Anaesthesia 42: 234–242.

    PubMed  CAS  Google Scholar 

  • Firestone, D., 1984. Chlorinated aromatic compounds and related dioxins and furans: Production, uses, and environmental exposure, in Banbury Report 18. Biological Mechanisms of Dioxin Action (A. Poland and R. D. Kimbrough, eds.), Cold Spring Harbor Laboratory, pp. 3–16.

    Google Scholar 

  • Forman, S. A., Verkman, A. S., Dix, J. A., and Solomon, A. K., 1985. n-Alkanols and halothane inhibit red cell anion transport and increase band 3 conformational change rate, Biochemistry 24: 4859–4866.

    Google Scholar 

  • Fukuta, T. R., 1976. Physicochemical aspects of insecticidal action, in Insect Biochemistry and Physiology ( C. F. Wilkenson, ed.), Plenum, New York, pp. 397–428.

    Google Scholar 

  • Gandolfi, O., Cheney, D. L., Hong, J. S., and Costa, E., 1984. On the neurotoxicity of chlordecone: A role for y-aminobutyric acid and serotonin, Brain Res. 303: 117–123.

    PubMed  CAS  Google Scholar 

  • Gelman, S., and Van Dyke, R., 1988. Mechanism of halothane-induced hepatotoxicity: Another step on a long road, Anesthesiology 68: 479–482.

    PubMed  CAS  Google Scholar 

  • Geyer, R. P., 1975. “Bloodless” rats through the use of artificial blood substitutes, Fed. Proc. 34:1499–1505.

    Google Scholar 

  • Goldstein, J. A., 1980. Structure-activity relationships for the biochemical effects and the relationships to toxicity, in Halogenated Biphenyls, Terphenyls, Naphthalenes, Dibenzodioxins and Related Products ( R. D. Kimbrough, ed.), Elsevier/North-Holland, Biomedical Press, Amsterdam, pp. 151–190.

    Google Scholar 

  • Hammond, B., Katzenellenbogen, B. S., Krauthammer, N., and McConnell, J., 1979. Estrogenic activity of the insecticide chlordecone (Kepone) and interaction with uterine estrogen receptors, Proc. Natl. Acad. Sci. USA 76: 6641–6645.

    PubMed  CAS  Google Scholar 

  • Hardy, R. N., Lowe, K. C., and McNaughton, D. C., 1983. Acute responses during blood substitution in the conscious rat, J. Physiol. 338: 451–461.

    PubMed  CAS  Google Scholar 

  • Hart, M. M., Reagan, R. L., and Adamson, R. H., 1973. The effects of isomers of DDD on the ACTH-induced steroid output, histology and ultrastructure of the dog adrenal cortex, Toxicol. Appl. Pharmacol. 24: 101–113.

    PubMed  CAS  Google Scholar 

  • Hayes, W. J., Jr., 1982. Chlorinated hydrocarbon insecticides, in Pesticides Studied in Man (W. J. Hayes, ed.), Williams and Wilkins, Baltimore, pp. 172–283.

    Google Scholar 

  • Herr, D. W., Gallus, J. A., and Tilson, H. A., 1987. Pharmacological modification of tremor and enhanced acoustic startle by chlordecone and p, p’-DDT, Psychopharmacology (Berlin) 91: 320–325.

    CAS  Google Scholar 

  • Hille, B., 1977. Ionic channels of nerve: Questions for theoretical chemists, BioSystems 8: 195–199.

    PubMed  CAS  Google Scholar 

  • Holan, G., 1969. New halocyclopropane insecticides and the mode of action of DDT, Nature 221: 1025–1029.

    PubMed  CAS  Google Scholar 

  • Holan, G., 1971. Rational design of degradable insecticides, Nature 232: 644 647.

    Google Scholar 

  • Hong, J. S., Tilson, H. A., Uphouse, L. L., Gerhart, J., and Wilson, W. E., 1984. Effects of chlordecone exposure on brain neurotransmitters: Possible involvement of the serotonin system in chlordecone-elicited tremor, Toxicol. Appl. Pharmacol. 73: 336–344.

    PubMed  CAS  Google Scholar 

  • Hong, J. S., Herr, D. W., Hudson, P. M., and Tilson, H. A., 1986. Neurochemical effects of DDT in rat brain in vivo, Arch. Toxicol., Suppl. 9: 14–26.

    CAS  Google Scholar 

  • Hong, L. H., McKinney, J. D., and Luster, M. I., 1987. Modulation of 2,3,7,8tetrachlorodibenzo -p-dioxin (TCDD)-mediated myelotoxicity by thyroid hormones, Biochem. Pharmacol. 36: 1361–1365.

    PubMed  CAS  Google Scholar 

  • Hrdina, P. D., Singhal, R. L., Peters, D. A. V., and Ling, G. M., 1973. Some neurochemical alterations during acute DDT poisoning, Toxicol. Appl. Pharmacol. 25: 276–288.

    PubMed  CAS  Google Scholar 

  • Hudson, P. M., Chen, P. H., Tilson, H. A., and Hong, J. S., 1985. Effects of p, p’-DDT on the rat brain concentrations of biogenic amine and amino acid neurotransmitters and their association with p, p’-DDT induced tremor and hyperthermia, J. Neurochem. 45: 1349–1355.

    PubMed  CAS  Google Scholar 

  • Jensen, B. L., Caldwell, M. W., French, L. G., and Briggs, D. G., 1987. Toxicity, ultrastructural effects, and metabolic studies with 1-(o-chlorophenyl)-1-(p-chloropheny1)-2,2dichloroethane (o, p’-DDD) and its methyl analog in the guinea pig and rat, Toxicol. Appl. Pharmacol. 87: 1–9.

    PubMed  CAS  Google Scholar 

  • Jordon, J. E., Grice, T., Mishra, S. K., and Desaiah, D., 1981. Acute chlordecone toxicity in rats: A relationship between tremor and ATPase activities, Neurotoxicology 2: 355–364.

    Google Scholar 

  • Joy, R. M., 1982. Chlorinated hydrocarbon insecticides, in Pesticides and Neurological Diseases ( D. J. Ecobichon and R. M. Joy, eds.), CRC Press, Boca Raton, Florida, pp. 91–150.

    Google Scholar 

  • Kaddus, A. A., Ghiasuddin, S. M., Matsumura, F., Scott, J. G., and Tanaka, K., 1983. Difference in the picrotoxinin receptor between the cyclodiene-resistant and susceptible strains of the German cockroach, Pestic. Biochem. Physiol. 19: 157–166.

    Google Scholar 

  • Kimbrough, R. D., 1980. Environmental pollution of air, water and soil, in Halogenated Biphenyls, Terphenyls, Naphthalenes, Dibenzodioxins and Related Products (R. D. Kimbrough, ed.), Elsevier/North-Holland Biomedical Press, Amsterdam, pp. 77–80.

    Google Scholar 

  • Kimbrough, R. D., 1984. Skin lesions in animals and humans: A brief overview, in Banbury Report 18. Biological Mechanisms of Dioxin Action (A. Poland and R. D. Kimbrough, eds.), Cold Spring Harbor Laboratory, pp. 357–363.

    Google Scholar 

  • Knutson, J. C., and Poland, A., 1982. Response of murine epidermis to 2,3,7,8-tetrachlorodibenzo-p-dioxin: Interaction of the Ah and hr loci, Cell 30: 225–234.

    PubMed  CAS  Google Scholar 

  • Komulainen, H., and Bondy, S. C., 1987. Modulation of levels of free calcium within synaptosomes by organochlorine insecticides, J. Pharmacol. Exp. Ther. 241: 575–581.

    PubMed  CAS  Google Scholar 

  • Korach, K. S., Sarver, P., Chae, K., McLachlan, J. A., and McKinney, J. D., 1988. Estrogen receptor-binding activity of polychlorinated hydroxybiphenyls: Conformationally restricted structural probes, Mol. Pharmacol. 33: 120–126.

    PubMed  CAS  Google Scholar 

  • Kress, H. G., Eckhardt-Wallasch, H., Tas, P. W. L., and Koschel, K., 1987. Volatile anesthetics depress the depolarization-induced cytoplasmic calcium rise in PC 12 cells, FEBS Lett. 221:28–32.

    Google Scholar 

  • Kupfer, D., 1975. Effects of pesticides and related compounds on steroid metabolism and functions, CRC Crit. Rev. Toxicol. 4: 83–124.

    PubMed  CAS  Google Scholar 

  • Lawrence, L. J., and Casida, J. E., 1984. Interactions of lindane, toxaphene and cyclodienes with brain-specific t-butylbicyclophosphorothionate receptor, Life Sci. 35: 171–178.

    PubMed  CAS  Google Scholar 

  • Lowe, K. C., 1987. Perfluorocarbons as oxygen-transport fluids, Comp. Biochem. Physiol. 87A: 825–838.

    CAS  Google Scholar 

  • Lowe, K. C., and McNaughton, D. C., 1985. Intravascular fluid composition following blood replacement with fluosol-DA in the rat, Br. J. Pharmacol. 84: 116 P.

    Google Scholar 

  • Lowe, K. C., and McNaughton, D. C., 1986. Changes in plasma enzyme concentrations in response to blood substitution with perfluorocarbon emulsion in the conscious rat, Experientia 42: 1228–1231.

    PubMed  CAS  Google Scholar 

  • Marshall, J. S., and Tompkins, L. S., 1968. Effects of o, p’-DDD and similar compounds on thyroxine binding globulin, J. Clin. Endocrin. Metab. 28: 386–392.

    CAS  Google Scholar 

  • Matsumura, F., 1975. Toxicology of Insecticides, Plenum Press, New York, pp. 165–251. Matsumura, F., and Ghiasuddin, S. M., 1983. Evidence for similarities between cyclodiene type insecticides and picrotoxinin in their action mechanisms, J. Environ. Sci. B 18: 1–14.

    Google Scholar 

  • McBlain, W. A., 1987. The levo enantiomer of o, p’-DDT inhibits the binding of 17ß-estradiol to the estrogen receptor, Life Sci. 40: 215–221.

    PubMed  CAS  Google Scholar 

  • McKinney, J. D., 1985. The molecular basis of chemical toxicity, Environ. Health Perspect. 61: 5–10.

    PubMed  CAS  Google Scholar 

  • McKinney, J. D., Long, G. A., and Pedersen, L., 1984. PCB and dioxin binding to cytosol receptors: A theoretical model based on molecular parameters, Quant. Struct.-Act. Relat. 3: 99–105.

    CAS  Google Scholar 

  • McKinney, J. D., Darden, T., Lyerly, M. A., and Pedersen, L. G., 1985a. PCB and related compound binding to the Ah receptor(s). Theoretical model based on molecular parameters and molecular mechanics, Quant. Struct: Act. Relat. 4: 166–172.

    CAS  Google Scholar 

  • McKinney, J. D., Chae, K., McConnell, E. E., and Birnbaum, L. S., 1985b. Structure-induction versus structure-toxicity relationships for polychlorinated biphenyls and related aromatic hydrocarbons, Environ. Health Perspect. 60: 57–68.

    PubMed  CAS  Google Scholar 

  • McKinney, J. D., Chae, K., Oatley, S. J., and Blake, C. C. F., 1985c. Molecular interactions of toxic chlorinated dibenzo-p-dioxins and dibenzofurans with thyroxine binding prealbumin, J. Med. Chem. 28: 375–381.

    PubMed  CAS  Google Scholar 

  • McKinney, J. D., Fawkes, J., Jordan, S., Chae, K., Oatley, S., Coleman, R. E., and Briner, W., 1985d. 2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) as a potent and persistent thyroxine agonist: A mechanistic model for toxicity based on molecular reactivity, Environ. Health Perspect. 61: 41–53.

    Google Scholar 

  • McKinney, J. D., Fannin, R., Jordan, S., Chae, K., Rickenbacher, U., and Pedersen, L., 1987. Polychlorinated biphenyls and related compound interactions with specific binding sites for thyroxine in rat liver nuclear extracts, J. Med. Chem. 30: 79–86.

    PubMed  CAS  Google Scholar 

  • Miller, K. W., 1985. Specific and nonspecific actions of general anesthetic agents, in Effects of Anesthesia ( B. G. Covino, H. A. Fozzard, K. Rehder, and G. Strichartz, eds.), American Physiological Society, Bethesda, Maryland, pp. 29–37.

    Google Scholar 

  • Narahashi, T., and Haas, G. H., 1967. DDT: Interaction with nerve membrane conductance changes, Science 157: 1438–1440.

    PubMed  CAS  Google Scholar 

  • Narahashi, T., and Haas, G. H., 1968. Interaction of DDT with the components of lobster nerve membrane conductance, J. Gen. Physiol. 51: 177–198.

    PubMed  CAS  Google Scholar 

  • Narahashi, T., and Yamasaki, T., 1960. Mechanisms of increase in negative afterpotential by dicophanum (DDT) in the giant axons of the cockroach, J. Physiol. 152: 122–140.

    PubMed  CAS  Google Scholar 

  • Neal, R. A., Beatty, P. W., and Gasiewicz, T. A., 1979. Studies on the mechanisms of toxicity of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD), Ann. N.Y. Acad. Sci. 320: 204–213.

    PubMed  CAS  Google Scholar 

  • Nebert, D. W., Eisen, H. J., Negishi, M., Lang, M. A., and Hjelmeland, L. M., 1981. Genetic mechanisms controlling the induction of polysubstrate monooxygenase (P-450) activities, Annu. Rev. Pharmacol. Toxicol. 21: 431–462.

    PubMed  CAS  Google Scholar 

  • Nelson, J. A., 1974. Effects of dichlorodiphenyltrichloroethane (DDT) analogs and polychlorinated biphenyl (PCB) mixtures on 17ß-[3H]estradiol binding to rat uterine receptors, Biochem. Pharmacol. 23: 447–451.

    PubMed  CAS  Google Scholar 

  • Poland, A., and Glover, E., 1973. Chlorinated dibenzo-p-dioxins: Potent inducers of S-aminolevulinic acid synthetase and aryl hydrocarbon hydroxylase, Mol. Pharmacol. 9: 736–747.

    PubMed  CAS  Google Scholar 

  • Poland, A., and Glover, E., 1977. Chlorinated biphenyl induction of aryl hydrocarbon hydroxylase activity: A study of the structure-activity relationship, Mol. Pharmacol. 13: 924–938.

    PubMed  CAS  Google Scholar 

  • Poland, A., and Knutson, J. C., 1982. 2,3,7,8-Tetrachlorodibenzo-p-dioxin and related halogenated aromatic hydrocarbons: Examination of the mechanism of toxicity, Annu. Rev. Pharmacol. Toxicol. 22: 517–554.

    Google Scholar 

  • Poland, A., Glover, E., and Kende, A. S., 1976. Stereospecific, high affinity binding of 2,3,7,8tetrachlorodibenzo-p-dioxin by hepatic cytosol. Evidence that the binding species is receptor for aryl hydrocarbon hydroxylase, J. Biol. Chem. 251: 4936–4946.

    PubMed  CAS  Google Scholar 

  • Prokocimer, P. G., Maze, M., Vickery, R. G., Kraemer, F. B., Gandjei, R., and Hoffman, B. B., 1988. Mechanism of halothane-induced inhibition of isoproterenol-stimulated lipolysis in rat adipocytes, Mol. Pharmacol. 33: 338–343.

    CAS  Google Scholar 

  • Quraishi, M. S., 1977. Biochemical Insect Control, Its Impact on Economy, Environment, and Natural Selection, John Wiley & Sons, New York, pp. 98–123.

    Google Scholar 

  • Reggiani, G., 1980. Localized contamination with TCDD-Seveso, Missouri and other areas, in Halogenated Biphenyls, Terphenyls, Naphthalenes, Dibenzodioxins and Related Products ( R. D. Kimbrough, ed.), Elsevier/North-Holland Biomedical Press, Amsterdam, pp. 303–371.

    Google Scholar 

  • Riess, J. G., and Le Blanc, M., 1982. Solubility and transport phenomena in perfluorochemicals relevant to blood substitution and other biomedical applications, Pure Appl. Chem. 54: 2382–2406.

    Google Scholar 

  • Rozman, K., Rozman, T., and Greim, H., 1984. Effects of thyroidectomy and thyroxine on 2,3,7,8-tetrachloro-p-dioxin (TCDD) induced toxicity, Toxicol. Appl. Pharmacol. 72: 372–376.

    PubMed  CAS  Google Scholar 

  • Safe, S., Bandiera, S., Sawyer, T., Robertson, L., Safe, L., Parkinson, A., Thomas, P. E., Ryan, D. E., Reik, L. M., Levin, W., Denomme, M. A., and Fujita, T., 1985. PCBs: Structure-function relationships and mechanism of action, Environ. Health Perspect. 60: 47–56.

    PubMed  CAS  Google Scholar 

  • Satoh, H., Davies, H. W., Takemura, T., Gillette, J. R., Maeda, K., and Pohl, L. R., 1987. An immunochemical approach to investigating the mechanism of halothane-induced hepatotoxicity, Prog. Drug Metab. 10: 187–206.

    CAS  Google Scholar 

  • Schieble, T. M., Costa, A. K., Heffel, D. F., and Trudell, J. R., 1988. Comparative toxicity of halothane, isoflurane, hypoxia, and phenobarbital induction in monolayer cultures of rat hepatocytes, Anesthesiology 68: 485–494.

    PubMed  CAS  Google Scholar 

  • Selinsky, B. S., Perlman, M. E., and London, R. E., 1988. In vivo nuclear magnetic resonance studies of hepatic methoxyflurane metabolism. II. A reevaluation of hepatic metabolic pathways, Mol. Pharmacol. 33: 567–573.

    CAS  Google Scholar 

  • Stoelting, R. K., 1987. Pharmacology and Physiology in Anesthetic Practice, J. B. Lippincott Co., Philadelphia, pp. 35–68.

    Google Scholar 

  • Stryer, L., 1988. Biochemistry, 3rd ed., W. H. Freeman and Co., New York, p. 1011.

    Google Scholar 

  • Tilson, H. A., Emerich, D., and Bondy, S. C., 1986a. Inhibition of ornithine decarboxylase alters neurological responsiveness to a tremorigen, Brain Res. 379: 147–150.

    PubMed  CAS  Google Scholar 

  • Tilson, H. A., Hudson, P. M., and Hong, J. S., 1986b. 5,5-Diphenylhydantoin antagonizes the neurochemical and behavioral effects of p, p’-DDT but not of chlordecone, J. Neurochem. 47: 1870–1878.

    Google Scholar 

  • Urban, B. W., 1985. Modifications of excitable membranes by volatile and gaseous anesthetics, in Effects of Anesthesia ( B. G. Covino, H. A. Fozzard, K. Rehder, and G. Strichartz, eds.), American Physiological Society, Bethesda, Maryland, pp. 13–28.

    Google Scholar 

  • van den Bercken, J.,1970. The effect of DDT and dieldrin on myelinated nerve fibres, Eur. J. Pharmacol. 20:205–214.

    Google Scholar 

  • Van Poznak, A., 1979. Methoxyflurane (PenthraneR): Seeking its niche, in Development of New Volatile Inhalation Anaesthetics ( A. B. Dobkin, ed.), Elsevier/North-Holland Press, Amsterdam, pp. 113–153.

    Google Scholar 

  • Van Woert, M. H., Plaitakis, A., and Hwang, E. C., 1982. Neurotoxic effects of DDT [1,1,1trichloro-2,2-bis(p-chlorophenyl)ethane]: Role of serotonin, in Mechanisms of Action of Neurotoxic Substances ( K. N. Prasad and A. Vernadakis, eds.), Raven Press, New York, pp. 143–154.

    Google Scholar 

  • Vos, J. G., 1984. Dioxin-induced thymic atrophy and the suppression of thymus-dependent immunity, in Banbury Report 18. Biological Mechanisms of Dioxin Action (A. Poland and R. D. Kimbrough, eds.), Cold Spring Harbor Laboratory, pp. 401–410.

    Google Scholar 

  • Whitlock, J. P., Jr., and Galeazzi, D. R., 1984. 2,3,7,8-Tetrachlorodibenzo p-dioxin receptors in wild type and variant mouse hepatoma cells. Nuclear location and strength of nuclear binding, J. Biol. Chem. 259: 980–985.

    Google Scholar 

  • Wilson, S. L., and Fabian, L. W., 1979. Inhalation anaesthetics: Going, going, gone, in Development of New Volatile Inhalation Anaesthetics (A. B. Dobkin, ed.), Elsevier/NorthHolland Press, Amsterdam, pp. 5–57.

    Google Scholar 

  • Woolley, D. E., 1982. Neurotoxicity of DDT and possible mechanisms of action, in Mechanisms of Action of Neurotoxic Substances ( K. N. Prasad and A. Vernadakis, eds.), Raven Press, New York, pp. 95–141.

    Google Scholar 

  • Wu, C. H., Oxford, G. S., Narahashi, T., and Holan, G., 1980. Interaction of a DDT analogue with the sodium channel of lobster axon, J. Pharmacol. Exp. Ther. 212: 287–293.

    PubMed  CAS  Google Scholar 

  • Wyrwicz, A. M., Schofield, J. C., Tillman, P. C., Gordon, R. E., and Martin, P. A., 1983. Noninvasive observations of fluorinated anesthetics in rabbit brain by fluorine-19 nuclear magnetic resonance, Science 222: 428–430.

    PubMed  CAS  Google Scholar 

  • Wyrwicz, A. M., Conboy, C. B., Ryback, K. R., Nichols, B. G., and Eisele, P., 1987. In vivo F-NMR study of isoflurane elimination from brain, Biochim. Biophys. Acta 927: 86–91.

    PubMed  CAS  Google Scholar 

  • Yeager, J., and Munson, S., 1945. Physiological evidence of a site of action of DDT in an insect, Science 102: 305–307.

    PubMed  CAS  Google Scholar 

  • Yokoyama, K., Suyama, T., and Naito, R., 1982. Development of perfluorochemical (PFC) emulsions as an artificial blood substitute, in Biomedicinal Aspects of Fluorine Chemistry ( R. Filler and Y. Kobayashi, eds.), Kodansha Ltd., Tokyo, and Elsevier Biomedical Press, Amsterdam, pp. 191–212.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1991 Plenum Press, New York

About this chapter

Cite this chapter

Kirk, K.L. (1991). Persistent Polyhalogenated Compounds: Biochemistry, Toxicology, Medical Applications, and Associated Environmental Issues. In: Biochemistry of the Elemental Halogens and Inorganic Halides. Biochemistry of the Elements, vol 9A+B. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-5817-6_8

Download citation

  • DOI: https://doi.org/10.1007/978-1-4684-5817-6_8

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4684-5819-0

  • Online ISBN: 978-1-4684-5817-6

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics