Skip to main content
SpringerLink
Log in

Soluble epoxide hydrolase

  • Chapter
Class 3 Hydrolases

Part of the book series: Springer Handbook of Enzymes ((HDBKENZYMES,volume S5))

  • 720 Accesses

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 259.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
Price excludes VAT (USA)
  • Durable hardcover 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

  1. Wixtrom, R.N.; Hammock, B.D.: Membrane-bound and soluble-fraction epoxide hydrolases. Biochem. Pharmacol. Toxicol., 1, 1–93 (1985)

    CAS  Google Scholar 

  2. Waechter, F.; Merdes, M.; Bieri, F.; Stäubli, W.; Bentley, P.: Purification and characterization of a soluble epoxide hydrolase from rabbit liver. Eur. J. Biochem., 125, 457–461 (1982)

    Article  PubMed  CAS  Google Scholar 

  3. Wang, P.; Meijer, J.; Guengerich, F.P.: Purification of human liver cytosolic epoxide hydrolase and comparison to the microsomal enzyme. Biochemistry, 21, 5769–5776 (1982)

    Article  PubMed  CAS  Google Scholar 

  4. Gill, S.S.: Purification of mouse liver cytosolic epoxide hydrolase. Biochem. Biophys. Res. Commun., 112, 763–769 (1983)

    Article  PubMed  CAS  Google Scholar 

  5. Meijer, J.; Depierre, J.W.: Properties of cytosolic epoxide hydrolase purified from the liver of untreated and clofibrate-treated mice. Purification procedure and physiochemical characterization of the pure enzymes. Eur. J. Biochem., 148, 421–430 (1985)

    Article  PubMed  CAS  Google Scholar 

  6. Prestwich, G.D.; Hammock, B.D.: Rapid purification of cytosolic epoxide hydrolase from normal and clofibrate-treated animals by affinity chromatography. Proc. Natl. Acad. Sci. USA, 82, 1663–1667 (1985)

    Article  PubMed  CAS  Google Scholar 

  7. Meijer, J.; Depierre, J.W.: Properties of cytosolic epoxide hydrolase purified from the liver of untreated and clofibrate-treated mice. Characterization of optimal assay conditions, substrate specificity and effects of modulators on the catalytic activity. Eur. J. Biochem., 150, 7–16 (1985)

    Article  PubMed  CAS  Google Scholar 

  8. Hammock, B.D.; Prestwich, G.D.; Loury, D.N.; Cheung, P.Y.K.; Eng, W.S.; Park, S.K.; Moody, D.E.; Silva, M.H.; Wixtrom, R.N.: Comparison of crude and affinity purified cytosolic epoxide hydrolases from hepatic tissue of control and clofibrate-fed mice. Arch. Biochem. Biophys., 244, 292–309 (1986)

    Article  PubMed  CAS  Google Scholar 

  9. Meijer, J.; DePierre, J.W.: Cytosolic epoxide hydrolase. Chem. Biol. Interact., 64, 207–249 (1988)

    Article  PubMed  CAS  Google Scholar 

  10. Wixtrom, R.N.; Silva, M.H.; Hammock, B.D.: Affinity purification of cytosolic epoxide hydrolase using derivatized epoxy-activated Sepharose gels. Anal. Biochem., 169, 71–80 (1988)

    Article  PubMed  CAS  Google Scholar 

  11. Schladt, L.; Hartman, R.; Woerner, W.; Thomas, H.; Oesch, F.; Purification and characterization of rat-liver cytosolic epoxide hydrolase. Eur. J. Biochem., 176, 31–37 (1988)

    Article  PubMed  CAS  Google Scholar 

  12. Schladt, L.; Thomas, H.; Hartmann, R.; Oesch, F.: Human liver cytosolic epoxide hydrolases. Eur. J. Biochem., 176, 715–723 (1988)

    Article  PubMed  CAS  Google Scholar 

  13. Miki, I.; Shimizu, T.; Seyama, Y.; Kitamura, S.; Yamaguchi, K.; Sano, H.; Ueno, H.; Hiratsuka, A.; Watanabe, T.: Enzymic conversion of 11,12-leukotriene A4 to 11,12-dihydroxy-5, 14-cis-7,9-trans-eicosatetraenoic acid. Purification of an epoxide hydrolase from the guinea pig liver cytosol. J. Biol. Chem., 264, 5799–5805 (1989)

    PubMed  CAS  Google Scholar 

  14. Arand, M.; Wagner, H.; Oesch, F.: Asp333, Asp495, and His523 form the catalytic triad of rat soluble epoxide hydrolase. J. Biol. Chem., 271, 4223–4229 (1996)

    Article  PubMed  CAS  Google Scholar 

  15. Pinot, F.; Grant, D.F.; Beetham, J.K.; Parker, A.G.; Borhan, B.; Landt, S.; Jones, A.D.; Hammock, B.D.: Molecular and biochemical evidence for the involvement of the Asp-333-His-523 pair in the catalytic mechanism of soluble epoxide hydrolase. J. Biol. Chem., 270, 7968–7974 (1995)

    Article  PubMed  CAS  Google Scholar 

  16. Blee, F.; Schuber, F.: Occurence of fatty acid epoxide hydrolases in soybean (Glycine max). Biochem. J., 282, 711–714 (1992)

    PubMed  CAS  Google Scholar 

  17. Morisseau, C.; Archelas, A.; Guitton, C.; Faucher, D.; Furstoss, R.; Baratti, J.C.: Purification and characterization of a highly enantioselective epoxide hydrolase from Aspergillus niger. Eur. J. Biochem., 263, 386–395 (1999)

    Article  PubMed  CAS  Google Scholar 

  18. Misawa, E.; Chan Kwo Chion, C.K.C.; Archer, I.V.; Woodland, M.P.; Zhou, N.Z.; Carter, S.F.; Widdowson, D.A.; Leak, D.J.: Characterisation of a catabolic epoxide hydrolase from a Corynebacterium sp.. Eur. J. Biochem., 253, 173–183 (1998)

    Article  PubMed  CAS  Google Scholar 

  19. Chang, C.; Gill, S.S.: Purification and characterization of an epoxide hydrolase from the peroxisomal fraction of mouse liver. Arch. Biochem. Biophys., 285, 276–284 (1991)

    Article  PubMed  CAS  Google Scholar 

  20. Halarnkar, P.P.; Nourooz-Zadeh, J.; Kuwano, E.; Jones, A.D.; Hammock, B.D.: Formation of cyclic products from the diepoxide of long-chain fatty esters by cytosolic epoxide hydrolase. Arch. Biochem. Biophys., 294, 586–593 (1992)

    Article  PubMed  CAS  Google Scholar 

  21. Nourooz-Zadeh, J.; Winder, B.S.; Dietze, E.C.; Giometti, C.S.; Tollaksen, S.L.; Hammock, B.D.: Biochemical characterization of a variant form of cytosolic epoxide hydrolase induced by parental exposure to N-ethyl-N-nitrosurea. Comp. Biochem. Physiol. C, 103, 207–214 (1992)

    Article  PubMed  CAS  Google Scholar 

  22. Dietze, E.C.; Magdalou, J.; Hammock, B.D.: Human and murine cytosolic epoxide hydrolase: Physical and structural properties. Int. J. Biochem., 22, 461–470 (1990)

    Article  PubMed  CAS  Google Scholar 

  23. Morisseau, C.; Beetham, J.K.; Pinot, F.; Debernard, S.; Newman, J.W.; Hammock, B.D.: Cress and potato soluble epoxide hydrolases: purification, biochemical characterization, and comparison to mammalian enzymes. Arch. Biochem. Biophys., 378, 321–332 (2000)

    Article  PubMed  CAS  Google Scholar 

  24. Thomas, H.; Schladt, L.; Doehmer, J.; Knehr, M.; Oesch, F.: Rat and human liver cytosolic epoxide hydrolases: evidence for multiple forms at the level of protein and mRNA. Environ. Health Perspect., 88, 49–55 (1990)

    Article  PubMed  CAS  Google Scholar 

  25. Summerer, S.; Hanano, A.; Utsumi, S.; Arand, M.; Schuber, F.; Blee, E.: Stereochemical features of the hydrolysis of 9,10-epoxystearic acid catalysed by plant and mammalian epoxide hydrolases. Biochem. J., 366, 471–480 (2002)

    Article  PubMed  CAS  Google Scholar 

  26. Rink, R.; Kingma, J.; Lutje Spelberg, J.H.; Janssen, D.B.: Tyrosine residues serve as proteon donor in the catalytic mechanism of epoxide hydrolase from Agrobacterium radiobacter. Biochemistry, 39, 5600–5613 (2000)

    Article  PubMed  CAS  Google Scholar 

  27. Gomez, G.A.; Morisseau, C.; Hammock, B.D.; Christianson, D.W.: Structure of human epoxide hydrolase reveals mechanistic inferences on bifunctional catalysis in epoxide and phosphate ester hydrolysis. Biochemistry, 43, 4716–4723 (2004)

    Article  PubMed  CAS  Google Scholar 

  28. Li, C.; Liu, Q.; Song, X.; Ding, D.; Ji, A.; Qu, Y.: Epoxide hydrolase-catalyzed resolution of ethyl 3-phenylglycidate using whole cells of Pseudomonas sp. Biotechnol. Lett., 25, 2113–2116 (2003)

    Article  PubMed  CAS  Google Scholar 

  29. Bellevik, S.; Zhang, J.; Meijer, J.: Brassica napus soluble epoxide hydrolase (BNSEH1). Eur. J. Biochem., 269, 5295–5302 (2002)

    Article  PubMed  CAS  Google Scholar 

  30. Nardini, M.; Rink, R.; Janssen, D.B.; Dijkstra, B.W.: Structure and mechanism of the epoxide hydrolase from Agrobacterium radiobacter AD1. J. Mol. Catal. B, 11, 1035–1042 (2001)

    Article  CAS  Google Scholar 

  31. Reetz, M.T.; Torre, C.; Eipper, A.; Lohmer, R.; Hermes, M.; Brunner, B.; Maichele, A.; Bocola, M.; Arand, M.; Cronin, A.; Genzel, Y.; Archelas, A.; Furstoss, R.: Enhancing the enantioselectivity of an epoxide hydrolase by directed evolution. Org. Lett., 6, 177–180 (2004)

    Article  PubMed  CAS  Google Scholar 

  32. Edqvvist, J.; Farbos, I.: A germination-specific epoxide hydrolase from Euphorbia lagascae. Planta, 216, 403–412 (2003)

    Google Scholar 

  33. Newman, J.W.; Morisseau, C.; Harris, T.R.; Hammock, B.D.: The soluble epoxide hydrolase encoded by EPXH2 is a bifunctional enzyme with novel lipid phosphate phosphatase activity. Proc. Natl. Acad. Sci. USA, 100, 1558–1563 (2003)

    Article  PubMed  CAS  Google Scholar 

  34. Bellevik, S.; Summerer, S.; Meijer, J.: Overexpression of Arabidopsis thaliana soluble epoxide hydrolase 1 in Pichia pastoris and characterisation of the recombinant enzyme. Protein Expr. Purif., 26, 65–70 (2002)

    Article  PubMed  CAS  Google Scholar 

  35. Zou, J.; Hallberg, B.M.; Bergfors, T.; Oesch, F.; Arand, M.; Mowbray, S.L.; Jones, T.A.: Structure of Aspergillus niger epoxide hydrolase at 1.8 A resolution: implications for the structure and function of the mammalian microsomal class of epoxide hydrolases. Structure Fold. Des., 8, 111–122 (2000)

    Article  PubMed  CAS  Google Scholar 

  36. Monfort, N.; Archelas, A.; Furstoss, R.: Enzymatic transformations. Part 55: Highly productive epoxide hydrolase catalyzed resolution of an azole antifungal key synthon. Tetrahedron, 60, 601–605 (2004)

    Article  CAS  Google Scholar 

  37. DuTeaux, S.B.; Newman, J.W.; Morisseau, C.; Fairbairn, E.A.; Jelks, K.; Hammock, B.D.; Miller, M.G.: Epoxide hydrolases in the rat epididymis: possible roles in xenobiotic and endogenous fatty acid metabolism. Toxicol. Sci., 78, 187–195 (2004)

    Article  PubMed  CAS  Google Scholar 

  38. Yu, Z.; Davis, B.B.; Morisseau, C.; Hammock, B.D.; Olson, J.L.; Kroetz, D.L.; Weiss, R.H.: Vascular localization of soluble epoxide hydrolase in the human kidney. Am. J. Physiol., 286, F720–726 (2004)

    Article  CAS  Google Scholar 

  39. Shin, J.-H.; Engidawork, E.; Delabar, J.-M.; Lubec, G.: Identification and characterization of soluble epoxide hydrolase in mouse brain by a robust protein biocehmical method. Amino Acids, 28, 63–69 (2005)

    Article  PubMed  CAS  Google Scholar 

  40. Jones, P.D.; Wolf, N.M.; Morisseau, C.; Whetstone, P.; Hock, B.; Hammock, B.D.: Fluorescent substrates for soluble epoxide hydrolase and application to inhibition studies. Anal. Biochem., 343, 66–75 (2005)

    Article  PubMed  CAS  Google Scholar 

  41. Morisseau, C.; Hammock, B.D.: Epoxide hydrolases: mechanisms, inhibitor designs, and biological roles. Annu. Rev. Pharmacol. Toxicol., 45, 311–333 (2005)

    Article  PubMed  CAS  Google Scholar 

  42. Zeldin, D.C.; Wei, S.; Falck, J.R.; Hammock, B.D.; Snapper, J.R.; Capdevila, J.H.: Metabolism of epoxyeicosatrienoic acids by cytosolic epoxide hydrolase: substrate structural determinants of asymmetric acatalysis. Arch. Biochem. Biophys., 316, 443–451 (1995)

    Article  PubMed  CAS  Google Scholar 

  43. Morisseau, C.; Du, G.; Newman, J.W.; Hammock, B.D.: Mechanism of mammalian soluble epoxide hydrolase inhibition by chalcone oxide derivatives. Arch. Biochem. Biophys., 356, 214–228 (1998)

    Article  PubMed  CAS  Google Scholar 

  44. Srivastava, P.K.; Sharma, V.K.; Kalonia, D.S.; Grant, D.F.: Polymorphisms in human soluble epoxide hydrolase: effects on enzyme activity, enzyme stability, and quarternary structure. Arch. Biochem. Biophys., 427, 164–169 (2004)

    Article  PubMed  CAS  Google Scholar 

  45. Arand, M.; Hemmer, H.; Duerk, H.; Barattis, J.; Archelas, A.; Furstoss, R.: Cloning and molecular characterization of a soluble epoxide hydrolase from Aspergillus niger that is related to mammalian microsomal epoxide hydrolase. Biochem. J., 344, 273–280 (1999)

    Article  PubMed  CAS  Google Scholar 

  46. Dietze, E.C.; Kuwano, E.; Casa, J.; Hammock, B.D.: Inhibition of cytosolic epoxide hydrolase by trans-3-phenylglycidols. Biochem. Pharmacol., 42, 1163–1175 (1991)

    Article  PubMed  CAS  Google Scholar 

  47. Tran, K.L.; Aronov, P.A.; Tanaka, H.; Newman, J.W.; Hammock, B.D.; Morisseau, C.: Lipid sulfates and sulfonates are allosteric competitive inhibitors of the N-terminal phosphatase activity of the mammalian soluble poxide hydrolase. Biochemistry, 44 12179–12187 (2005)

    Article  PubMed  CAS  Google Scholar 

  48. Lacourciere, G.M.; Armstrong, R.N.: Microsomal ans soluble epoxide hydrolases are members of the same family of C-X bond hydrolase enzymes. Chem. Res. Toxicol., 7, 121–124 (1994)

    Article  PubMed  CAS  Google Scholar 

  49. Yu, Z.; Xu, F.; Huse, L.M.; Morisseau, C.; Draper, A.J.; Newman, J.W.; Parker, C.; Graham, L., Engler, M.M.; Hammock, B.D.; Zeldin, D.C.; Kroetz, D.L.: Soluble expoxide hydrolase regulates hydrolysis of vasoactive epoxyeicosatrienoic acids. Circ. Res., 87, 992–998 (2000)

    PubMed  CAS  Google Scholar 

  50. Dietze, E.C.; Stephens J.; Magdalou, J.; Bender, D.M.; Moyer, M.; Fowler, B.; Hammock, B.D.: Inhibition of human and murine cytosolic epoxide hydrolase by group-selective reagents. Comp. Biochem. Physiol. B, 104, 299–308 (1993)

    Article  PubMed  CAS  Google Scholar 

  51. Arahira, M.; Nong, V.H.; Udaka, K.; Fukazawa, C.: Purification, molecular cloning and ethylene-inducible expression of a soluble-type epoxide hydrolase from soybean (Glycine max [L.] Merr.). Eur. J. Biochem., 267, 2649–2657 (2000)

    Article  PubMed  CAS  Google Scholar 

  52. Sellers, K.W.; Sun, C.; Diez-Freire, C.; Waki, H.; Morisseau, C.; Falck, J.R.; Hammock, B.D.; Paton, J.F.; Raizada, M.K.: Novel mechanism of brain soluble epoxide hydrolase-mediated blood pressure regulation in the spontaneously hypertensive rat. FASEB J., 19, 626–628 (2005)

    PubMed  CAS  Google Scholar 

  53. Mullen, R.T.; Trelease, R.N.; Duerk, H.; Arand, M.; Hammock, B.D.; Oesch, F.; Grnat, D.F.: Differential subcellular localization of endogenous and transfected soluble epoxide hydrolase in mammalian cells: evidence for isozyme variants. FEBS Lett., 445 301–305 (1999)

    Article  PubMed  CAS  Google Scholar 

  54. Dietze, E.D.; Kuwano, E.; Hammock, B.D.: The interaction of cytosolic epoxide hydrolase with chiral epoxides. Int. J. Biochem., 25, 43–52 (1993)

    Article  PubMed  CAS  Google Scholar 

  55. Schiott, B.; Bruice, T.C.: Reaction mechanism of soluble epoxide hydrolase: insights from molecular dynamics simulations. J. Am. Chem. Soc., 124, 14558–14570 (2002)

    Article  PubMed  CAS  Google Scholar 

  56. Haeggstroem, J.; Meijer, J.; Radmark, O.: Leukotriene A4. Enzymatic conversion into 5,6-dihydroxy-7,9,11,14-eicosatetraenoic acid by mouse liver cytosolic epoxide hydrolase. J. Biol. Chem., 261, 6332–6337 (1986)

    CAS  Google Scholar 

  57. Enayetallah, A.E.; French, R.A.; Barber, M.; Grant, D.F.: Cell-specific subcellular localization of soluble epoxide hydrolase in human tissues. J. Histochem. Cytochem., 54, 329–335 (2006)

    Article  PubMed  CAS  Google Scholar 

  58. McElroy, N.R.; Jurs, P.C.: QSAR and classification of murine and human soluble epoxide hydrolase inhibition by urea-like compounds. J. Med. Chem., 46, 1066–1080 (2003)

    Article  PubMed  CAS  Google Scholar 

  59. Stapleton, A.; Beetham, J.K.; Pinot, F.; Garbarino, J.E.; Rockhold, D.R.; Friedman, M.; Hammock, B.D.; Belknap, W.R.: Cloning and expression of soluble epoxide hydrolase from potato. Plant J., 6, 251–258 (1994)

    Article  PubMed  CAS  Google Scholar 

  60. Harris, T.R.; Morisseau, C.; Walzem, R.L.; Ma, S.J.; Hammock, B.D.: The cloning and characterization of a soluble epoxide hydrolase in chicken. Poult. Sci., 85, 278–287 (2006)

    PubMed  CAS  Google Scholar 

  61. Cronin, A.; Mowbray, S.; Duerk, H.; Homburg, S.; Fleming, I.; Fisslthaler, B.; Oesch, F.; Arand, M.: The N-terminal domain of mammalian soluble epoxide hydrolase is a phosphatase. Proc. Natl. Acad. Sci. USA, 100, 1552–1557 (2003)

    Article  PubMed  CAS  Google Scholar 

  62. Schmelzer, K.R.; Kubala, L.; Newman, J.W.; Kim, I.-H.; Eiserich, J.P.; Hammock, B.D.: Soluble epoxide hydrolase is a therapeutic target for acute inflammation. Proc. Natl. Acad. Sci. USA, 102, 9772–9777 (2005)

    Article  PubMed  CAS  Google Scholar 

  63. Newman, J.W.; Morisseau, C.; Hammock, B.D.: Epoxide hydrolases: their roles and interactions with lipid metabolism. Prog. Lipid Res., 44, 1–51 (2005)

    Article  PubMed  CAS  Google Scholar 

  64. Gomez, G.A.; Morisseau, C.; Hammock, B.D.; Christianson, D.W.: Human soluble expoxide hydrolase: structural basis of inhibition by 4-(3-cyclohexylureido)-carboxylic acids. Protein Sci., 15, 58–64 (2006)

    Article  PubMed  CAS  Google Scholar 

  65. Ota, K.; Hammock, B.D.: Cytosolic and microsomal epoxide hydrolases: differential properties in mammalian liver. Science, 207, 1479–1480 (1980)

    Article  PubMed  CAS  Google Scholar 

  66. Draper, A.J.; Hammock, B.D.: Inhibition of soluble and microsomal epoxide hydrolase by zinc and other metals. Toxicol. Sci., 52, 26–32 (1999)

    Article  PubMed  CAS  Google Scholar 

Download references

Editor information

Editors and Affiliations

  1. Technical University Braunschweig Bioinformatics & Systems Biology, Langer Kamp 19b, 38106, Braunschweig, Germany

    Antje Chang

Rights and permissions

Reprints and permissions

Copyright information

© 2009 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

(2009). Soluble epoxide hydrolase. In: Chang, A. (eds) Class 3 Hydrolases. Springer Handbook of Enzymes, vol S5. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-85703-7_37

Download citation

Publish with us

Policies and ethics

Search

Navigation