Urea and amide-based inhibitors of the juvenile hormone epoxide hydrolase of the tobacco hornworm (Manduca sexta: Sphingidae)

Insect Biochemistry and Molecular Biology

Volumn 32, Issue 12, 2002, Pages 1741-1756

  Severson, Tonya F ^a   Goodrow, Marvin H ^a,b   Morisseau, Christophe ^a   Dowdy, Deanna L ^a   Hammock, Bruce D ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UC Davis ^*  (United States)

Author keywords

Amide; Carbamates; Inhibitors; Juvenile hormone epoxide hydrolase; Kinetics; Manduca sexta; Metabolism; Structure activity relationships (SAR); Urea

Indexed keywords

AMIDE; EPOXIDE HYDROLASE; JUVENILE HORMONE EPOXIDE HYDROLASE; UREA;

ANIMAL; ARTICLE; DRUG ANTAGONISM; ENZYME SPECIFICITY; ENZYMOLOGY; KINETICS; LEPIDOPTERA; METABOLISM;

AMIDES; ANIMALS; EPOXIDE HYDROLASES; KINETICS; MANDUCA; SUBSTRATE SPECIFICITY; UREA;

MAMMALIA; MANDUCA SEXTA; NICOTIANA TABACUM; SPHINGIDAE;

EID: 0036891429     PISSN: 09651748     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0965-1748(02)00115-7     Document Type: Article

References (43)

1. Argiriadi, M.A., Morisseau, C., Goodrow, M.H., Dowdy, D.L., Hammock, B.D., Christianson, D.W., 2000. Binding of alkylurea inhibitors to epoxide hydrolase implicates active site tyrosines in substrate activation. J. Biol. Chem. 275, 15265-15270.
2. Argiriadi, M.A., Morisseau, C., Hammock, B.D., Christianson, D.W., 1999. Detoxification environmental mutagens and carcinogens: Structure, mechanism, and evolution of liver epoxide hydrolase. Proc. Natl Acad. Sci. USA 96, 10637-10642.
3. Armstrong, R.N., 1999. Kinetic and chemical mechanism of epoxide hydrolase. Drug Metab. Rev. 31, 71-86.
4. Armstrong, R.N., Cassidy, C.S., 2000. New structural and chemical insight into the catalytic mechanism of epoxide hydrolases. Drug. Metab. Rev. 32, 327-338.
5. Borhan, B., Mebrahtu, T., Nazarian, S., Kurth, M.J., Hammock, B.D., 1995. Improved radiolabeled substrates for soluble epoxide hydrolases. Anal. Biochem. 231, 188-200.
6. Brooks, G.T., 1973. Insect epoxide hydrase inhibition by juvenile hormone analogues and metabolic inhibitors. Nature 245, 382-384.
7. Campbell, P.M., Healy, M.J., Oakeshott, J.G., 1992. Characterization of juvenile hormone esterase in Drosophila melanogaster. Insect Biochem. Mol. Biol. 22, 665-677.
8. Casas, J., Harshman, L.G., Hammock, B.D., 1991a. Epoxide hydrolase activity on juvenile hormone in Manduca sexta. Insect Biochem. 21, 17-26.
9. Casas, J., Harshman, L.G., Messeguer, A., Kuwano, E., Hammock, B.D., 1991b. In vitro metabolism of juvenile hormone III and juvenile hormone III bisepoxide by Drosophila melanogaster and mammalian cytosolic epoxide hydrolase. Arch. Biochem. Biophys. 286, 153-158.
10. De Kort, C.A.D., Granger, N.A., 1981. Regulation of the juvenile hormone titer. Ann. Rev. Entomol. 26, 1-28.
11. De Kort, C.A.D., Granger, N.A., 1996. Regulation of JH titers: The relevance of degradative enzymes and binding proteins. Arch. Insect Biochem. Physiol. 33, 1-26.
12. Debernard, S., Morisseau, C., Severson, T.F., Feng, L., Wojtasek, H., Prestwich, G.D., Hammock, B.D., 1998. Expression and characterization of the recombinant juvenile hormone epoxide hydrolase (JHEH) from Manduca sexta. Insect Biochem. Mol. Biol. 28, 409-419.
13. Dietze, E.C., Kuwano, E., Casas, J., 1991. Inhibition of cytosolic epoxide hydrolase by trans-3-phenylglycidols. Biochem. Pharmacol. 42, 1163-1175.
14. Halarnkar, P.P., Schooley, D.A., 1990. Reversed-phase liquid chromatographic esparation of juvenile hormone and its metabolites, and its application for an in vivo juvenile hormone catabolism study in Manduca sexta. Anal. Biochem. 188, 394-397.
15. Hammock, B.D., 1985. Regulation of juvenile hormone titer: Degradation. In: Kerkut, G.A., Gilbert, L.I. (Eds.), Comprehensive Insect Physiology, Biochemistry and Pharmacology. Pergamon Press, Oxford, pp. 431-472.
16. Hammock, B.D., Mumby, S.M., Lee, P.W., 1977. Mechanisms of resistance to the juvenoid methoprene in the house fly Musca domestica L. Pestic. Biochem. Phys. 7, 261-272.
17. Hammock, B.D., Nowock, J., Goodman, W., Stamoudis, V., Gilbert, L.I., 1975. The influence of hemolymph-binding protein on juvenile hormone stability and distribution in Manduca sexta fat body and imaginal discs in vivo. Mol. Cell Endocrinol. 3, 167-184.
18. Hammock, B.D., Roe, R.M., 1985. Analysis of juvenile hormone esterase activity. In: Law, J.H., Rilling, H.C. (Eds.), Methods in Enzymology: Steroids and Isoprenoids. Academic Press, New York, pp. 487-494.
19. Jesudason, P., Anspaugh, D.D., Roe, R.M., 1992. Juvenile hormone metabolism in the plasma, integument, midgut, fat body, and brain during the last instar of the tobacco hornworm, Manduca sexta. Arch. Insect Biochem. Physiol. 20, 87-105.
20. Kramer, K.J., Sanburg, L.L., Kezdy, F.J., Law, J.H., 1974. The juvenile hormone binding protein in the hemolymph of Manduca sexta Johannson (Lepidoptera: Sphingidae). Proc. Natl Acad. Sci. USA 71, 493-497.
21. Lassiter, M.T., Apperson, C.S., Roe, R.M., 1995. Juvenile hormone metabolism during the fourth stadium and pupal stage of the southern house mosquito, Culex quinquefasciatus Say. J. Insect Physiol. 41, 869-876.
22. Linderman, R.J., Roe, R.M., Harris, S.V., Thompson, D.M., 2000. Inhibition of insect juvenile hormone epoxide hydrolase: Asymmetric synthesis and assay of glycidol-ester and epoxyester inhibitors of Trichoplusia ni epoxide hydrolase. Insect Biochem. Mol. Biol. 30, 767-774.
23. McGovern, S.L., Caselli, E., Grigorieff, N., Shoichet, B.K., 2002. A common mechanism underlying promiscuous inhibitors from virtual and high-throughput screening. J. Med. Chem. 45, 1712-1722.
24. Miyamoto, T., Silva, M., Hammock, B.D., 1987. Inhibition of epoxide hydrolases and glutathione S-transferases by 2-, 3-, and 4-substituted derivatives of 4′-phenylchalcone and its oxide. Arch. Biochem. Biophys. 254, 203-213.
25. Morisseau, C., Du, G., Newman, J.W., Hammock, B.D., 1998. Mechanism of mammalian soluble epoxide hydrolase inhibition by chalcone oxide derivatives. Arch. Biochem. Biophys. 356, 214-228.
26. Morisseau, C., Newman, J.W., Dowdy, D.L., Goodrow, M.H., Hammock, B.D., 2001. Inhibition of microsomal epoxide hydrolases by ureas, amides and amines. Chem. Res. Toxicol 14, 409-415.
27. Morisseau, C.H., Goodrow, M.H., Dowdy, D., Zheng, J., Greene, J.F., Sanborn, J.R., Hammock, B.D., 1999. Potent urea and carbamate inhibitors of soluble epoxide hydrolases. Proc. Natl Acad. Sci. USA 96, 8849-8854.
28. Mullin, C.A., Hammock, B.D., 1982. Chalcone oxides - Potent selective inhibitors of cytosolic epoxide hydrolase. Arch. Biochem. Biophys. 216, 423-439.
29. Mumby, S.M., Hammock, B.D., 1979. A partition assay for epoxide hydrases acting on insect juvenile hormone and an epoxide-containing juvenoid. Anal. Biochem. 92, 16-21.
30. Nijhout, H.F., 1994. Insect Hormones. Princeton University Press, Princeton, NJ.
31. Share, M.R., Venkatesh, K., Jesudason, P., Roe, R.M., 1988. Juvenile hormone metabolism during embryogenesis in the tobacco hornworm Manduca sexta (L.). Arch. Insect Biochem. Physiol. 8, 173-186.
32. Slade, M., Brooks, G.T., Hemarski, H.K., Wilkinson, C.F., 1975. Inhibition of the enzymatic hydration of the epoxide HEOM in insects. Pestic. Biochem. Physiol. 5, 35-46.
33. Slade, M., Zibitt, C.H., 1971. Metabolism of Cecropia juvenile hormone in Lepidopterans. In: Tahori, A.S. (Ed.), Chemical Releases in Insects. Gordon & Breach, pp. 45-58.
34. Slade, M., Zibitt, C.H., 1972. Metabolism of Cecropia juvenile hormone in insects and in mammals. In: Menn, J.J., Beroza, M. (Eds.), Insect Juvenile Hormones: Chemistry and Action. Academic Press, New York, pp. 155-176.
35. Sparks, T.C., Hammock, B.D., 1980. Comparative inhibition of the juvenile hormone esterases from Trichoplusia ni, Tenebrio molitor, Musca domestica. Pestic. Biochem. Physiol. 14, 290-302.
36. Sparks, T.C., Hammock, B.D., Riddiford, L.M., 1983. The haemolymph juvenile hormone esterase of Manduca sexta (L.) - Inhibition and regulation. Insect Biochem. 13, 529-541.
37. Touhara, K., Prestwich, G.D., 1993. Juvenile hormone epoxide hydrolase: Photoaffinity labeling, purification, and characterization from tobacco hornworm eggs. J. Biol. Chem. 268, 19604-19609.
38. Williamson, K.C., Morisseau, C., Hammock, B.D., 2000. Regio- and enantioselective hydrolysis of phenyloxiranes catalyzed by soluble epoxide hydrolase. Tetrahedron 11, 4451-4462.
39. Wing, K.D., Sparks, T.C., Lovell, V.M., Levinson, S.O., Hammock, B.D., 1981. The distribution of juvenile hormone esterase and its interrelationship with other proteins influencing juvenile hormone metabolism in the cabbage looper, Trichoplusia ni. Insect Biochem. 11, 473-485.
40. Wojtasek, H., Prestwich, G.D., 1996. An insect juvenile hormone-specific epoxide hydrolase is related to vertebrate microsomal epoxide hydrolase. Biochem. Biophys. Res. Co. 220, 323-329.
41. Yamada, T., Morisseau, C., Maxwell, J.E., Argiriadi, M.A., Christianson, D.W., Hammock, B.D., 2000. Biochemical evidence for the involvement of tyrosine in epoxide activation during the catalytic cycle of epoxide hydrolase. J. Biol. Chem. 275, 23082-23088.
42. 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., et al. 2000. Soluble epoxide hydrolase regulates hydrolysis of vasoactive epoxyeicosatrienoic acids. Circ. Res. 87, 992-998.
43. Zou, J., Hallberg, B.M., Bergfors, T., Oesch, F., Arand, M., Mowbray, S.L., Jones, T.A., 2000. 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 8, 111-122.