Substrate specificity for the epoxidation of terpenoids and active site topology of house fly cytochrome P450 6A1

Chemical Research in Toxicology

Volumn 10, Issue 2, 1997, Pages 156-164

  Andersen, John F ^a   Walding, Jennifer K ^a   Evans, Philip H ^a   Bowers, William S ^a   Feyereisen, René ^a  

^a UNIVERSITY OF ARIZONA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; TERPENOID;

ARTICLE; ENZYME ACTIVE SITE; ENZYME SPECIFICITY; ENZYME SUBSTRATE; EPOXIDATION; ESCHERICHIA COLI; HOUSE FLY; NONHUMAN; PROTEIN EXPRESSION; STEREOCHEMISTRY;

ANIMALS; BINDING SITES; CATALYSIS; CYTOCHROME P-450 ENZYME SYSTEM; EPOXY COMPOUNDS; FATTY ACIDS, UNSATURATED; HOUSEFLIES; ISOMERISM; OXIDATION-REDUCTION; SUBSTRATE SPECIFICITY; TERPENES;

ESCHERICHIA COLI; INSECTA; MUSCA DOMESTICA;

EID: 0031042230     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9601162     Document Type: Article

References (44)

1. Carino, F., Koener, J. F., Plapp, F. W., Jr., and Feyereisen, R. (1992) Expression of the cytochrome P450 gene CYP6A1 in the house fly, Musca domestica. ACS Symp. Ser. 505, 31-40.
2. Cariño, F. A., Koener, J. F., Plapp, F. W., Jr., and Feyereisen, R. (1994) Constitutive overexpression of the cytochrome P450 gene CYP6A1 in a house fly strain with metabolic resistance to insecticides. Insect Biochem. Mol. Biol. 24, 411-418.
3. Andersen, J. F., Utermohlen, J. G., and Feyereisen, R. (1994) Expression of house fly CYP6A1 and NADPH-cytochrome P450 reductase in E. coli and reconstitution of an insecticide-metabolizing P450 system. Biochemistry 33, 2171-2177.
4. Plapp, F. W., Jr., and Vinson, S. B. (1973) Juvenile hormone analogs: toxicity and resistance in the housefly. Pestic. Biochem. Physiol. 5, 233-241.
5. Hammock, B. D., and Quistad, G. B. (1981) Metabolism and mode of action of juvenile hormone, juvenoids and other insect growth regulators. In Progress in Pesticide Biochemistry (Hutson, D. H., and Roberts, T. R., Eds.) Vol. 1, pp 1-83, John Wiley and Sons, New York.
6. Forman, B. M., Goode, E., Chen, J., Oro, A. E., Bradley, D. J., Perlmann, T., Noonan, D. J., Burka, L. T., McMorris, T. Lamph, W. W., Evans, R. M., and Weinberger, C. (1995) Identification of a nuclear receptor that is activated by farnesol metabolites. Cell 81, 687-693.
7. Harmon, M. A., Boehm, M. F., Heyman, R. A., and Mangelsdorf, D. J. (1995) Activation of mammalian retinoid X receptors by the insect growth regulator methoprene. Proc. Natl. Acad. Sci. U.S.A. 92, 6157-6160.
8. Koener, J. F., Cariño, F. A., and Feyereisen, R. (1993) The cDNA and deduced protein sequence of house fly NADPH-cytochrome P450 reductase. Insect Biochem. Mol. Biol. 23, 439-447.
9. Omura, T., and Sato, R. (1964) The carbon monoxide-binding pigment of liver microsomes I. Evidence for its hemeprotein nature. J. Biol. Chem. 239, 2370-2378.
10. Anderson, R. J., Henrick, C. A., Siddall, J. B., and Zurfluh, R. (1972) Stereoselective synthesis of the racemic C-17 juvenile hormone of Cecropia. J. Am. Chem. Soc. 94, 5379-5386.
11. Nilles, G. P., Zabik, M. J., Connin, R. V., and Schuetz, R. D. (1973) Synthesis of bioactive compounds: Juvenile hormone mimetics affecting insect diapause. J. Agric. Food Chem. 21, 342-347.
12. Richard, D. S., Applebaum, S. W., Sliter, T. J., Baker, F. C., Schooley, D. A., Reuter, C. C., Henrich, V. C., and L. I. Gilbert, L. I. (1989) Juvenile hormone bisepoxide biosynthesis in vitro by the ring gland of Drosophila melanogaster: A putative juvenile hormone in the higher Diptera. Proc. Natl. Acad. Sci. U.S.A. 86, 1421-1425.
13. Feyereisen, R. (1985) Radiochemical assay for juvenile hormone III biosynthesis in vitro. Methods Enzymol. 111, 530-539.
14. Schooley, D. A. (1977) Analysis of the naturally occurring juvenile hormones - their isolation, identification, and titer determination at physiological levels. In Analytical biochemistry of insects. (Turner, R. B., Ed.) Elsevier Scientific Publishing, Amsterdam.
15. BM3). In-situ rearrangement of their phenyl-iron complexes. J. Biol. Chem. 267, 5614-5620.
16. Liedtke, R. J., and Djerassi, C. (1972) Mass spectrometry in structural and stereochemical problems. CCXVII. The electron impact induced behavior of terpenoid esters of the juvenile hormone class. J. Org. Chem. 37, 2111-2118.
17. Herlt, A. J., Rickards, R. W., Thomas, R. D., and East P. D. (1993) The absolute configuration of juvenile hormone III bisepoxide. J. Chem. Soc., Chem. Commun. 1497-1498.
18. Judy, K. J., Schooley, D. A., Dunham, L. L., Hall, M. S., Bergot, B. J., and Siddall, J. B. (1973) Isolation, structure and absolute configuration of a new natural insect juvenile hormone from Manduca sexta. Proc. Natl. Acad. Sci. U.S.A. 70, 1509-1513.
19. Feyereisen, R., Pratt, G. E., and Hamnett, A. F. (1981) Enzymic synthesis of juvenile hormone in locust corpora allata. Evidence for a microsomal cytochrome P-450 linked methyl farnesoate epoxidase. Eur. J. Biochem. 118, 231-238.
20. Andersen, J. F., Ceruso, M., Unnithan, G. C., Kuwano, E., Prestwich, G. D., and Feyereisen, R. (1995) Photoaffinity labeling of methyl farnesoate epoxidase in cockroach corpora allata. Insect Biochem. Mol. Biol. 25, 713-719.
21. Ajami, A. M., and Riddiford, L. M. (1973) Comparative metabolism of the cecropia juvenile hormone. J. Insect Physiol. 19, 635-645
22. Hammock, B. D., Mumby, S. M., and Lee, P. W. (1977) Mechanisms of resistance to the juvenoid methoprene in the house fly, Musca domestica. Pest. Biochem. Physiol. 7, 261-272.
23. Yu, S. J., and Terriere, L. C. (1978) Metabolism of juvenile hormone I by microsomal oxidase, esterase, and epoxide hydrolase of Musca domestica and some comparisons with Phormia regina and Sarcophage bullata. Pest Biochem. Physiol. 9, 237-246.
24. Fisher, C. W., and Mayer, R. T. (1982) Characterization of house fly microsomal mixed function oxidases: inhibition by juvenile hormone I and piperonyl butoxide. Toxicology 24, 15-31.
25. Feyereisen, R., Koener, J. F., Farnsworth, D. E., and Nebert, D. W. (1989) Isolation and sequence of cDNA encoding a cytochrome P-450 from an insecticide-resistant strain of the house fly Musca domestica. Proc. Natl. Acad. Sci. U.S.A. 86, 1465-1469.
26. Terriere, L. C., and Yu, S. J. (1973) Insect juvenile hormones: Induction of detoxifying enzymes in the housefly and detoxication by housefly enzymes. Pestic. Biochem. Physiol. 3, 96-107.
27. Yu, S. J., and Terriere, L. C. (1975) Microsomal metabolism of juvenile hormone analogs in the house fly, Musca domestica, L. Pestic. Biochem. Physiol. 5, 418-430.
28. Quistad, G. B., Staiger, L. E., and Schooley, D. A. (1975) Environmental degradation of the insect growth regulator methoprene. Pestic. Biochem. Physiol. 5, 233-241.
29. 14C]hydroprene (ethyl 3,7,11-trimethyl-2,4-dodecadienoate) by microsomal oxidases and esterases from three species of Diptera. J. Agric. Food Chem. 25, 1076-1080.
30. Oguri, K., Yamada, H., and Yoshimura, H. (1994) Regiochemistry of cytochrome P450 isozymes. Annu. Rev. Pharmacol. Toxicol. 34, 251-279.
31. Wilkinson, C. F., Hetnarski, K., Cantwell, G. P., and DiCarlo, F. J. (1974) Structure - activity relationships in the effects of 1-alkyl-imidazoles on microsomal oxidation in vitro and in vivo. Biochem. Pharmacol. 23, 2377-2386.
32. Fruetel, J. A., Mackman, R. L., Peterson, J. A., and Ortiz de Montellano, P. R. (1994) Relationship of active site topology to substrate specificity for cytochrome P450terp (CYP108). J. Biol. Chem. 269, 28815-28821.
33. Ravichandran, K. G., Bodupalli, S. S., Hasemann, C. A., Peterson, J. A., and Deisenhofer, J. (1993) Crystal structure of hemoprotein domain of P450BM-3, a prototype for microsomal P450's. Science 261, 731-736.
34. Hasemann, C. A., Ravichandran, K. G., Peterson, J. A., and Deisenhofer, J. (1994) Crystal structure and refinement of cytochrome P450terp at 2.3 Å resolution. J. Mol. Biol. 236, 1169-1185.
35. cam iron-phenyl complex. Biochemistry 29, 8119-8126.
36. Ortiz de Montellano, P. R., and Graham-Lorence, S. E. (1993) Structure of cytochrome P450: heme binding site and heme reactivity. In Cytochrome P450 (Schenkman, J. B., and Greim, H., Eds.) pp 169-181, Springer-Verlag, Berlin.
37. cam (CYP101) F87W and F87A mutants. Evidence for significant structural rearrangemnt without alteration of catalytic regiospecificity. J. Biol. Chem. 268, 269-275.
38. Tuck, S. F., Hiroya, K., Shimuzu, M., Hatano, M., and Ortiz de Montellano, P. R. (1993) The cytochrome P450 active site: Topology and perturbations caused by glutamic acid-318 and threonine-319 mutations. Biochemistry 32, 2548-2553.
39. scc) and evidence for interaction of tyrosine 94 with the side chain of cholesterol. Arch. Biochem. Biophys. 322, 189-197.
40. Schooley, D. A., and Baker F. C. (1985) Juvenile hormone biosynthesis. In Comprehensive Insect Physiology, Biochemistry and Pharmacology (Kerkut, G. A., and Gilbert, L. I., Eds.) Vol. 7, pp 363-389, Pergamon Press, Oxford, England.
41. Hammock, B. D. (1975) NADPH-dependent epoxidation of methyl farnesoate to juvenile hormone in the cockroach Blaberus giganteus. L. Life Sci. 17, 323-328.
42. Lefevere, K. S., Lacey, M. J., Smith, P. H., and Roberts, B. 1993) Identification and quantification of juvenile hormone biosynthesized by larval and adult Australian sheep blowfly Lucilia cuprina (Diptera: Calliphoridae). Insect Biochem. Mol. Biol. 23, 713-720.
43. Moshitsky, P., and Applebaum, S. W. (1995) Pathway and regulation of JH III bisepoxide biosynthesis in adult Drosophila melanogaster corpus allatum. Arch. Insect Biochem. Physiol. 30, 225-237.
44. Casas, J., Harshman, L. G., Messeguer, A., Kuwano, E., and Hammock, B. D. (1991) In vitro metabolism of juvenile hormone III and juvenile hormone III bisepoxide by Drosophila melanogaster and mammalian epoxide hydrolase. Arch. Biochem. Biophys. 286, 153-158.