Drosophila melanogaster CYP6A8, an insect P450 that catalyzes lauric acid (ω-1)-hydroxylation

Biochemical and Biophysical Research Communications

Volumn 325, Issue 4, 2004, Pages 1495-1502

  Helvig, Christian ^a   Tijet, Nathalie ^a   Feyereisen, René ^b   Walker, F Ann ^a   Restifo, Linda L ^a  

^a UNIVERSITY OF ARIZONA   (United States)

^b CEMAGREF   (France)

Author keywords

Cytochrome P450; Development; Drosophila melanogaster; Fatty acids; HPLC; Hydroxylation; Insecticides; Lauric acid

Indexed keywords

ALDRIN; CYTOCHROME P450; HEPTACHLOR; LAURIC ACID;

ARTICLE; CONTROLLED STUDY; DROSOPHILA MELANOGASTER; ENZYME ACTIVITY; GENE IDENTIFICATION; GENETIC CODE; GENOME; NONHUMAN; PRIORITY JOURNAL; PROTEIN ANALYSIS; SACCHAROMYCES CEREVISIAE;

ALDRIN; ALKANE 1-MONOOXYGENASE; ANIMALS; CATALYSIS; CYTOCHROME P-450 ENZYME SYSTEM; DROSOPHILA MELANOGASTER; LAURIC ACIDS; MIXED FUNCTION OXYGENASES;

DROSOPHILA MELANOGASTER; INSECTA; MELANOGASTER; SACCHAROMYCES; SACCHAROMYCES CEREVISIAE;

EID: 8844252431     PISSN: 0006291X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbrc.2004.10.194     Document Type: Article

References (65)

1. D. Werck-Reichhart, and R. Feyereisen Cytochromes P450: a success story Genome Biol. 1 2000 3003.1 3003.9 (Reviews)
2. F.P. Guengerich Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity Chem. Res. Toxicol. 6 2001 611 650
3. K. Inouye, and T. Sakaki Enzymatic studies on the key enzymes of vitamin D metabolism; 1 alpha-hydroxylase (CYP27B1) and 24-hydroxylase (CYP24) Biotechnol. Annu. Rev. 7 2001 179 194
4. D.W. Nebert, and D.W. Russell Clinical importance of the cytochromes P450 Lancet 360 2002 1155 1162
5. A.O. Oyekan, K. McAward, and J.C. McGiff Renal functional effects of endothelins: dependency on cytochrome P450-derived arachidonate metabolites Biol. Res. 31 1998 209 215
6. J.H. Capdevila, and J.R. Falck The CYP P450 arachidonic acid monooxygenases: from cell signaling to blood pressure regulation Biochem. Biophys. Res. Commun. 285 2001 571 576
7. J.H. Capdevila, R.C. Harris, and J.R. Falck Microsomal cytochrome P450 and eicosanoid metabolism Cell. Mol. Life Sci. 59 2002 780 789
8. Y. Kikuta, E. Kusunose, and M. Kusunose Prostaglandin and leukotriene omega-hydroxylases Prostaglandins Other Lipid Mediat. 68-69 2002 345 362
9. R. Feyereisen Insect P450 enzymes Annu. Rev. Entomol. 44 1999 507 533
10. B.C. Dunkov, V.M. Guzov, G. Mocelin, F. Shotkoski, A. Brun, M. Amichot, R.H. Ffrench-Constant, and R. Feyereisen The D. melanogaster cytochrome P450 gene Cyp6a2: structure, localization, heterologous expression, and induction by phenobarbital DNA Cell Biol. 16 1997 1345 1356
11. C. Saner, B. Weibel, F.E. Wurgler, and C. Sengstag Metabolism of promutagens catalyzed by Drosophila melanogaster CYP6A2 enzyme in Saccharomyces cerevisiae Environ. Mol. Mutagen. 27 1996 46 58
12. M. Amichot, S. Tares, A. Brun-Barale, L. Arthaud, J.M. Bride, and J.B. Berge Point mutations associated with insecticide resistance in the Drosophila cytochrome P450 Cyp6a2 enable DDT metabolism Eur. J. Biochem. 271 2004 1250 1257
13. J.-S. He, and A.J. Fulco A barbiturate-regulated protein binding to a common sequence in the cytochrome P450 genes of rodents and bacteria J. Biol. Chem. 266 1991 7864 7869
14. G.C. Shaw, and A.J. Fulco Inhibition by barbiturates of the binding of Bm3R1 repressor to its operator site on the barbiturate-inducible cytochrome P450BM-3 gene of Bacillus megaterium J. Biol. Chem. 268 1993 2997 3004
15. L.C. Waters, A.C. Zelhof, B.J. Shaw, and L.-Y. Ch'ang Possible involvement of the long terminal repeat of transposable element 17.6 in regulating expression of an insecticide resistance-associated P450 gene in Drosophila Proc. Natl. Acad. Sci. USA 89 1992 4855 4859
16. M. Amichot, A. Brun, A. Cuany, C. Helvig, J.P. Salaun, F. Durst, and J.B. Berge Expression study of CYP genes in Drosophila strains resistant or sensitive to insecticides M.-C. Lechner Cytochrome P450. Biochemistry Biophysics and Molecular Biology 1994 John Libbey Eurotext Paris 689 692
17. A. Brun, A. Cuany, T. Le Mouel, J. Berge, and M. Amichot Inducibility of the Drosophila melanogaster cytochrome P450 gene, CYP6A2, by phenobarbital in insecticide susceptible or resistant strains Insect Biochem. Mol. Biol. 26 1996 697 703
18. S.M. Dombrowski, R. Krishnan, M. Witte, S. Maitra, C. Diesing, L.C. Waters, and R. Ganguly Constitutive and barbital-induced expression of the Cyp6a2 allele of a high producer strain of CYP6A2 in the genetic background of a low producer strain Gene 221 1998 69 77
19. V.M. Chavez, G. Marques, J.P. Delbecque, K. Kobayashi, M. Hollingsworth, J. Burr, J.E. Natzle, and M.B. O'Connor The Drosophila disembodied gene controls late embryonic morphogenesis and codes for a cytochrome P450 enzyme that regulates embryonic ecdysone levels Development 127 2000 4115 4126
20. L.I. Gilbert Halloween genes encode P450 enzymes that mediate steroid hormone biosynthesis in Drosophila melanogaster Mol. Cell. Endocrinol. 215 2004 1 10
21. R. Niwa, T. Matsuda, T. Yoshiyama, T. Namiki, K. Mita, Y. Fujimoto, and H. Kataoka CYP306A1, a cytochrome P450 enzyme, is essential for ecdysteroid biosynthesis in the prothoracic glands of Bombyx and Drosophila J. Biol. Chem. 279 2004 35942 35949
22. J.T. Warren, A. Petryk, G. Marques, J.P. Parvy, T. Shinoda, K. Itoyama, J. Kobayashi, M. Jarcho, Y. Li, M.B. O'Connor, C. Dauphin-Villemant, and L.I. Gilbert Phantom encodes the 25-hydroxylase of Drosophila melanogaster and Bombyx mori: a P450 enzyme critical in ecdysone biosynthesis Insect Biochem. Mol. Biol. 34 2004 991 1010
23. A. Petryk, J.T. Warren, G. Marques, M.P. Jarcho, L.I. Gilbert, J. Kahler, J.P. Parvy, Y. Li, C. Dauphin-Villemant, and M.B. O'Connor Shade is the Drosophila P450 enzyme that mediates the hydroxylation of ecdysone to the steroid insect molting hormone 20-hydroxyecdysone Proc. Natl. Acad. Sci. USA 100 2003 13773 13778
24. J.T. Warren, A. Petryk, G. Marques, M. Jarcho, J.P. Parvy, C. Dauphin-Villemant, M.B. O'Connor, and L.I. Gilbert Molecular and biochemical characterization of two P450 enzymes in the ecdysteroidogenic pathway of Drosophila melanogaster Proc. Natl. Acad. Sci. USA 99 2002 11043 11048
25. M.D. Adams, S.E. Celniker, R.A. Holt, C.A. Evans, J.D. Gocayne, P.G. Amanatides, S.E. Scherer, P.W. Li, R.A. Hoskins, R.F. Galle, R.A. George, S.E. Lewis, S. Richards, M. Ashburner, S.N. Henderson, G.G. Sutton, J.R. Wortman, M.D. Yandell, Q. Zhang, L.X. Chen, R.C. Brandon, Y.H. Rogers, R.G. Blazej, M. Champe, B.D. Pfeiffer, K.H. Wan, C. Doyle, E.G. Baxter, G. Helt, C.R. Nelson, G.L. Gabor, J.F. Abril, A. Agbayani, H.J. An, C. Andrews-Pfannkoch, D. Baldwin, R.M. Ballew, A. Basu, J. Baxendale, L. Bayraktaroglu, E.M. Beasley, K.Y. Beeson, P.V. Benos, B.P. Berman, D. Bhandari, S. Bolshakov, D. Borkova, M.R. Botchan, J. Bouck, P. Brokstein, P. Brottier, K.C. Burtis, D.A. Busam, H. Butler, E. Cadieu, A. Center, I. Chandra, J.M. Cherry, S. Cawley, C. Dahlke, L.B. Davenport, P. Davies, B. de Pablos, A. Delcher, Z. Deng, A.D. Mays, I. Dew, S.M. Dietz, K. Dodson, L.E. Doup, M. Downes, S. Dugan-Rocha, B.C. Dunkov, P. Dunn, K.J. Durbin, C.C. Evangelista, C. Ferraz, S. Ferriera, W. Fleischmann, C. Fosler, A.E. Gabrielian, N.S. Garg, W.M. Gelbart, K. Glasser, A. Glodek, F. Gong, J.H. Gorrell, Z. Gu, P. Guan, M. Harris, N.L. Harris, D. Harvey, T.J. Heiman, J.R. Hernandez, J. Houck, D. Hostin, K.A. Houston, T.J. Howland, M.H. Wei, C. Ibegwam, M. Jalali, F. Kalush, G.H. Karpen, Z. Ke, J.A. Kennison, K.A. Ketchum, B.E. Kimmel, C.D. Kodira, C. Kraft, S. Kravitz, D. Kulp, Z. Lai, P. Lasko, Y. Lei, A.A. Levitsky, J. Li, Z. Li, Y. Liang, X. Lin, X. Liu, B. Mattei, T.C. McIntosh, M.P. McLeod, D. McPherson, G. Merkulov, N.V. Milshina, C. Mobarry, J. Morris, A. Moshrefi, S.M. Mount, M. Moy, B. Murphy, L. Murphy, D.M. Muzny, D.L. Nelson, D.R. Nelson, K.A. Nelson, K. Nixon, D.R. Nusskern, J.M. Pacleb, M. Palazzolo, G.S. Pittman, S. Pan, J. Pollard, V. Puri, M.G. Reese, K. Reinert, K. Remington, R.D. Saunders, F. Scheeler, H. Shen, B.C. Shue, I. Siden-Kiamos, M. Simpson, M.P. Skupski, T. Smith, E. Spier, A.C. Spradling, M. Stapleton, R. Strong, E. Sun, R. Svirskas, C. Tector, R. Turner, E. Venter, A.H. Wang, X. Wang, Z.Y. Wang, D.A. Wassarman, G.M. Weinstock, J. Weissenbach, S.M. Williams, T. Woodage, K.C. Worley, D. Wu, S. Yang, Q.A. Yao, J. Ye, R.F. Yeh, J.S. Zaveri, M. Zhan, G. Zhang, Q. Zhao, L. Zheng, X.H. Zheng, F.N. Zhong, W. Zhong, X. Zhou, S. Zhu, X. Zhu, H.O. Smith, R.A. Gibbs, E.W. Myers, G.M. Rubin, and J.C. Venter The genome sequence of Drosophila melanogaster Science 287 2000 2185 2195
26. N. Tijet, C. Helvig, and R. Feyereisen The cytochrome P450 gene superfamily in Drosophila melanogaster: annotation, intron-exon organization and phylogeny Gene 262 2001 189 198
27. S. Maitra, S.M. Dombrowski, L.C. Waters, and R. Ganguly Three second chromosome-linked clustered Cyp6 genes show differential constitutive and barbital-induced expression in DDT-resistant and susceptible strains of Drosophila melanogaster Gene 180 1996 165 171
28. G. Le Goff, S. Boundy, P.J. Daborn, J.L. Yen, L. Sofer, R. Lind, C. Sabourault, L. Madi-Ravazzi, and R.H. ffrench-Constant Microarray analysis of cytochrome P450 mediated insecticide resistance in Drosophila Insect Biochem. Mol. Biol. 33 2003 701 708
29. J.H. Pedra, L.M. McIntyre, M.E. Scharf, and B.R. Pittendrigh Genome-wide transcription profile of field- and laboratory-selected dichlorodiphenyltrichloroethane (DDT)-resistant Drosophila Proc. Natl. Acad. Sci. USA 101 2004 7034 7039
30. S. Maitra, S.M. Dombrowski, M. Basu, O. Raustol, L.C. Waters, and R. Ganguly Factors on the third chromosome affect the level of Cyp6a2 and Cyp6a8 expression in Drosophila melanogaster Gene 248 2000 147 156
31. F.A. Carino, J.F. Koener, F.W. Plapp Jr., and R. Feyereisen Constitutive overexpression of the cytochrome P450 gene CYP6A1 in a house fly strain with metabolic resistance to insecticides Insect Biochem. Mol. Biol. 24 1994 411 418
32. 5, P450 reductase and monooxygenase activities in LPR house flies, Musca domestica Biochem. Genet. 34 1996 133 148
33. Q. Liang, and A.J. Fulco Transcriptional regulation of the genes encoding cytochromes P450BM-1 and P450BM-3 in Bacillus megaterium by the binding of Bm3R1 repressor to Barbie box elements and operator sites J. Biol. Chem. 270 1995 18606 18614
34. S. Maitra, C. Price, and R. Ganguly Cyp6a8 of Drosophila melanogaster: gene structure, and sequence and functional analysis of the upstream DNA Insect Biochem. Mol. Biol. 32 2002 859 870
35. A. Cuany, M. Pralavorio, D. Pauron, J.B. Berge, D. Fournier, C. Blais, R. Lafont, J.P. Salaun, D. Weissbart, C. Larroque, and R. Lange Characterization of microsomal oxidative activities in a wild-type and in a DDT resistant strain of Drosophila melanogaster Pestic. Biochem. Physiol. 37 1990 293 302
36. A. Cuany, C. Helvig, M. Amichot, P. Pflieger, C. Mioskowski, J.P. Salaun, D. Pauron, C. Larroque, and J.B. Berge Fate of a terminal olefin with Drosophila microsomes and its inhibitory effects on some P-450 dependent activities Arch. Insect Biochem. Physiol. 28 1995 325 338
37. S.R. Elgin, and D.W. Miller Mass rearing of flies and mass production and harvesting of eggs M. Ashburner T.R.F. Wright The Genetics and Biology of Drosophila vol. 2A 1978 Academic Press New York 112 121
38. S.P. Bainbridge, and M. Bownes Staging the metamorphosis of Drosophila melanogaster J. Embryol. Exp. Morph. 66 1981 57 80
39. B.T. Hovemann, F. Sehlmeyer, and J. Malz Drosophila melanogaster NADPH-cytochrome P450 oxidoreductase: pronounced expression in antennae may be related to odorant clearance Gene 189 1997 213 219
40. S. Bauer, and J. Shiloach Maximal exponential growth rate and yield of E. coli obtainable in a bench-scale fermentor Biotechnol. Bioeng. 16 1974 933 941
41. C. Helvig, and J.H. Capdevila Biochemical characterization of rat P450 2C11 fused to rat or bacterial NADPH-P450 reductase domains Biochemistry 39 2000 5196 5205
42. M.B. Murataliev, A. Ariño, V.M. Guzov, and R. Feyereisen Kinetic mechanism of cytochrome P450 reductase from the house fly (Musca domestica) Insect Biochem. Mol. Biol. 29 1999 233 242
43. H. Towbin, T. Staehelin, and J. Gordon Electrophoretic transfer of proteins from polyacrylamide gels to nitrocellulose sheets: procedure and some applications Proc. Natl. Acad. Sci. USA 76 1979 4350 4354
44. R. Feyereisen, and D.R. Vincent Characterization of antibodies to housefly NADPH-cytochrome-P-450 reductase Insect Biochem. 14 1984 163 168
45. D. Pompon, B. Louerat, A. Bronine, and P. Urban Yeast expression of animal and plant P450s in optimized redox environments Methods Enzymol. 272 1996 51 64
46. D. Gietz, A. St Jean, R.A. Woods, and R.H. Schiestl Improved method for high efficiency transformation of intact yeast cells Nucleic Acids Res. 20 1992 1425
47. T. Omura, and R. Sato The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature J. Biol. Chem. 239 1964 2370 2378
48. J.F. Andersen, J.G. Utermohlen, and R. Feyereisen Expression of house fly CYP6A1 and NADPH-cytochrome P450 reductase in Escherichia coli and reconstitution of an insecticide-metabolizing P450 system Biochemistry 33 1994 2171 2177
49. T.D. Sutherland, G.C. Unnithan, J.F. Andersen, P.H. Evans, M.B. Murataliev, L.Z. Szabo, E.A. Mash, W.S. Bowers, and R. Feyereisen A cytochrome P450 terpenoid hydroxylase linked to the suppression of insect juvenile hormone synthesis Proc. Natl. Acad. Sci. USA 95 1998 12884 12889
50. C. Helvig, J.F. Koener, G.C. Unnithan, and R. Feyereisen CYP15A1, the cytochrome P450 that catalyzes epoxidation of methyl farnesoate to juvenile hormone III in cockroach corpora allata Proc. Natl. Acad. Sci. USA 101 2004 4024 4029
51. M.B. Murataliev, and R. Feyereisen Interaction of NADP(H) with oxidized and reduced P450 reductase during catalysis. Studies with nucleotide analogs Biochemistry 39 2000 5066 5074
52. I. Benveniste, B. Gabriac, and F. Durst Purification and characterization of the NADPH-cytochrome P-450 (cytochrome c) reductase from higher-plant microsomal fraction Biochem. J. 235 1986 365 373
53. R. Feyereisen, and F. Durst Development of microsomal cytochrome P-450 monooxygenases during the last larval instar of the locust, Locusta migratoria: correlation with the hemolymph 20-hydroxyecdysone titer Mol. Cell. Endocrinol. 20 1980 157 169
54. M.J.J. Ronis, E. Hodgson, and W.C. Dauterman Characterization of multiple forms of cytochrome-P-450 from an insecticide resistant strain of house-fly (Musca-domestica) Pestic. Biochem. Physiol. 32 1988 74 90
55. S.E. Clarke, C.J. Brealey, and G.G. Gibson Cytochrome-P-450 in the housefly-induction, substrate-specificity and comparison to 3 rat hepatic isoenzymes Xenobiotica 19 1989 1175 1180
56. R.L. Rose, F. Gould, P.E. Levi, and E. Hodgson Differences in cytochrome-P450 activities in tobacco budworm larvae as influenced by resistance to host plant allelochemicals and induction Comp. Biochem. Physiol. B Biochem. Mol. Biol. 99 1991 535 540
57. N. Tijet, C. Helvig, F. Pinot, R. Le Bouquin, A. Lesot, F. Durst, J.P. Salaun, and I. Benveniste Functional expression in yeast and characterization of a clofibrate-inducible plant cytochrome P-450 (CYP94A1) involved in cutin monomers synthesis Biochem. J. 332 1998 583 589
58. N. Forthoffer, C. Helvig, N. Dillon, I. Benveniste, A. Zimmerlin, F. Tardif, and J.P. Salaun Induction and inactivation of a cytochrome P450 conferring herbicide resistance in wheat seedlings Eur. J. Drug Metab. Pharmacokinet. 26 2001 9 16
59. P.R. Green, and B.W. Geer Changes in the fatty acid composition of Drosophila melanogaster during development and ageing Arch. Int. Physiol. Biochim. 87 1979 485 491
60. R.H. Ffrench-Constant, N. Anthony, K. Aronstein, T. Rocheleau, and G. Stilwell Cyclodiene insecticide resistance: from molecular to population genetics Annu. Rev. Entomol. 45 2000 449 466
61. I. Lesscharve, D. Langlois, and P. Etiévant Volatile compounds in strawberry jam: influence of cooking on volatiles J. Food Sci. 56 1991 1393 1398
62. A. López-Villalobos, P.F. Dodds, and R. Hornung Changes in fatty acid composition during development of tissues of coconut (Cocos nucifera L.) embryos in the intact nut and in vitro J. Exp. Botany 52 2001 933 942
63. T. Duncan, G. Kutty, G.J. Chader, and B. Wiggert A glycoprotein binding retinoids and fatty acids is present in Drosophila Arch. Biochem. Biophys. 312 1994 158 166
64. K. Shim, W.L. Picking, R.K. Kutty, C.F. Thomas, B.N. Wiggert, and W.S. Stark Control of Drosophila retinoid and fatty acid binding glycoprotein expression by retinoids and retinoic acid: northern, western and immunocytochemical analyses Exp. Eye Res. 65 1997 717 727
65. H. Imaishi, Y. Matsumoto, U. Ishitobi, and H. Ohkawa Encoding of a cytochrome P450-dependent lauric acid monooxygenase by CYP703A1 specifically expressed in the floral buds of Petunia hybrida Biosci. Biotechnol. Biochem. 63 1999 2082 2090