Cytochromes P450 - A family of proteins and scientists-understanding their relationships

Drug Metabolism Reviews

Volumn 38, Issue 1-2, 2006, Pages 209-225

  Masters, Bettie Sue ^a,b   Marohnic, Christopher C ^a  

^a UNIVERSITY OF TEXAS HEALTH SCIENCE CENTER AT SAN ANTONIO   (United States)

^b Mays Cancer Center at UT Health San Antonio   (United States)

Author keywords

Antley Bixler syndrome; Arachidonic acid; CYP4A gene subfamily; CYPOR; CYPOR polymorphisms; Cytochrome b5; Eicosanoids; Fatty Acids; NADPH cytochrome P450 reductase; Prostaglandins

Indexed keywords

ARACHIDONIC ACID; CYTOCHROME B5; CYTOCHROME P450; CYTOCHROME P450 4A; DRUG; FATTY ACID; ICOSANOID; PROSTAGLANDIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE FERRIHEMOPROTEIN REDUCTASE; STEROID; UNSPECIFIC MONOOXYGENASE;

ANTLEY BIXLER SYNDROME; DRUG HYDROXYLATION; ELECTRON TRANSPORT; ENZYME ACTIVITY; GENETIC POLYMORPHISM; HYDROXYLATION; MUTATION; PROTEIN FAMILY; REVIEW;

ANIMALS; ARACHIDONIC ACID; CYTOCHROME P-450 ENZYME SYSTEM; ELECTRON TRANSPORT; FATTY ACIDS; HUMANS; MICROSOMES, LIVER; MUTATION; NADPH-FERRIHEMOPROTEIN REDUCTASE; PROSTAGLANDINS; STEROIDS;

EID: 33646681244     PISSN: 03602532     EISSN: 10979883     Source Type: Journal    
DOI: 10.1080/03602530600570065     Document Type: Review

References (98)

1. 1 and arachidonic acid. Arch. Biochem. Biophys. 393:329-338.
2. Aleck, K. A., Bartley, D. L. (1997). Multiple malformation syndrome following fluconazole use in pregnancy: report of an additional patient. Am. J. Med. Genet. 72:253-256.
3. Antley, R. M., Bixler, D. (1975). Trapezoidocephaly, midface hypoplasia and cartilage abnormalities with multiple synostoses and skeletal fractures. Birth Defects Orig. Art. Ser. XI(2):397-401.
4. Aoki, Y., Yoshihara, F., Kondoh, M., Nakamura, Y., Nakayama, N., Arisawa, M. (1993). Ro 0-1470 is a selective inhibitor of P-450 lanosterol C-14 demethylase of fungi. Antimicrob. Agents Chemother. 37:2662-2667.
5. Arlt, W., Walker, E. A., Draper, N., lvison, H. E., Ride, J. P., Hammer, F., Chalder, S. M., Borucka-Mankiewicz, M., Hauffa, B. P., Malunowicz, E. M., Stewart, P. M., Shackleton, C. H. (2004). Congenital adrenal hyperplasia caused by mutant P450 oxidoreductase and human androgen synthesis: analytical study. Lancet. 363:2128-2135.
6. 5 augments the 17,20-Lyase activity of human P450c17 without direct direct electron transfer. J. Biol. Chem. 273:3158-3165.
7. Auchus, R. J., Miller, W. L. (1999). Molecular modeling of human P450c17 (17a-hydroxylase/17,20-lyase): insights into reaction mechanisms and effects of mutations. Mol. Endocrinol. 13:1169-1182.
8. Black, S. D., French, J. S., Williams, C. H., Coon, M. J. (1979). Role of a hydrophobic polypeptide in the N-terminal region of NADPH-cytochrome P-450 reductase in complex formation with P-450LM. Biochem. Biophys. Res. Commun. 91:1528-1535.
9. 2. J. Biol. Chem. 256:9457-9465.
10. 5 and cytochrome P450 reductase. J. Biol. Chem. 273:17036-17049.
11. Capdevila, J., Parkhill, L., Chacos, N., Okita, R., Masters, B. S., Estabrook, R. W. (1981). The oxidative metabolism of arachidonic acid by purified cytochromes P-450. Biochem. Biophys. Res. Commun. 101:1357-1363.
12. Chitayat, D., Chun, K. (1999). Reply to the letter to the editor by Gripp et al. - 'not Antley-Bixler syndrome'. (Letter). Am. J. Med. Genet. 83:67-68.
13. Chun, K., Siegel-Bartelt, J., Chitayat, D., Phillips, J., Ray, P. N. (1988). FGFR2 mutation associated with clinical manifestations consistent with Antley-Bixler syndrome. Am. J. Med. Genet. 77:219-224.
14. 5 reduction. Arch. Biochem. Biophys. 143:37-45.
15. Cohen, B., Estabrook, R. W. (1971b). Microsomal electron transport reactions. II. The use of reduced triphosphopyridine nucleotide and/or reduced diphosphopyridine nucleotide for the oxidative N-demethylation of aminopyrine and other drug substrates. Arch. Biochem. Biophys. 143:46-53.
16. Cohen, B., Estabrook, R. W. (1971c). Microsomal electron transport reactions. III. Cooperative interactions between reduced diphosphopyridine nucleotide and reduced triphosphopyridine nucleotide linked reactions. Arch. Biochem. Biophys. 143:54-65.
17. Cooper, D. Y., Cannon, M. D., Schleyer, H., Rosenthal, O. (1977). Reductive titration of cytochrome P-450 in rat liver microsomes. J. Biol. Chem. 252:4755-4757.
18. Davydov, D. R., Kariakin, A. A., Petushkova, N. A., Peterson, J. A. (2000). Association of cytochromes P450 with their reductases: opposite sign of the electrostatic interactions in P450BM-3 as compared with the microsomal 2B4 system. Biochemistry 39:6489-6497.
19. DeLozier, C. D., Antley, R. M., Williams, R., Green, N., Heller, R. M., Bixler, D., Engel, E. (1980). The syndrome of multisynostotic osteodysgenesis with long-bone fractures. Am. J. Med. Genet. 7:391-403.
20. Devereux, T. R., Fouts, J. R. (1975). Effect of pregnancy or treatment with cetain steroids on N, N-dimethylaniline demethylation and N-oxidation by rabbit liver or lung microsomes. Drug Metab. Dispos. 3:254-258.
21. 5 reduction by NADPH-cytochrome P-450 reductase. J. Biol. Chem. 254:8976-8981.
22. Estabrook, R. W., Cooper, D. Y., Rosenthal, O. (1963). The light-reversible carbon monoxide inhibition of the steroid C-21 hydroxylation system of the adrenal cortex. Biochem. Zeit. 338:741-755.
23. Filler, R., Lew, K. J. (1981). Developmental onset of mixed-function oxidase activity in preimplantation mouse embryos. Proc. Natl. Acad. Sci. USA. 78:6991-6995.
24. Fisher, C. W., Shet, M. S., Estabrook, R. W. (1996). Construction of plasmids and expression in Escherichia coli of enzymatically active fusion proteins containing the heme-domain of a P450 linked to NADPH-P450 reductase. Methods Enzymol. 272:15-25.
25. Flück, C. E., Tajima, T., Pandy, A. V., Arlt, W., Okuhara, K., Verge, C. F., Jabs, E. W., Mendonça, B. B., Fujieda, K., Miller, W. L. (2004). Mutant P450 oxidoreductase causes disordered steroidogenesis with and without Antley-Bixler syndrome. Nat. Genet. 36:228-230.
26. Geller, D. H., Auchus, R. J., Mendonça, B. B., Miller, W. L. (1997). The genetic and functional basis of isolated 17,20-lyase deficiency. Nat. Genet. 17:201-205.
27. Gillette, J. R., Brodie, B. B., La Du, B. N. (1957). The oxidation of drugs by liver microsomes: on the role of TPNH and oxidase. J. Pharmacol. Exp. Ther. 119:532-540.
28. Glazer, R. I., Schenkman, J. B., Sartorelli, A. C. (1971). Immunochemical studies on the role of reduced nicotinamide adenine dinucleotide phosphate-cytochrome c reductase (P-450) reductase in drug oxidation. Mol. Pharmacol. 7:683-688.
29. Gonczy, P., Echeverri, C., Oegema, K., Coulson, A., Jones, S. J., Copley, R. R., Duperon, J., Oegema, J., Brehm, M., Cassin, E., Hannak, E., Kirkham, M., Pichler, S., Flohrs, K., Goessen, A., Leidel, S., Alleaume, A. M., Martin, C., Ozlu, N., Bork, P., Hyman, A. A. (2000). Functional genomic analysis of cell division in C. elegans using RNAi of genes on chromosome III. Nature 408:331-336.
30. rd ed. New York: Kluwer Academic/Plenum Publishers. pp. 377-530.
31. Hasemann, C. A., Kurumbail, R. G., Boddupalli, S. S., Peterson, J. A., Deisenhofer, J. (1995). Structure and function of cytochromes P450: a comparative analysis of three crystal structures. Structure 3:41-62.
32. Henderson, C. J., Otto, D. M., Carrie, D., Magnuson, M. A., McLaren, A. W., Rosewell, I., Wolf, C. R. (2003). Inactivation of the hepatic cytochrome P450 system by conditional deletion of hepatic cytochrome P450 reductase. J. Biol. Chem. 278:13480-13486.
33. 5 in hepatic microsomal mixed-function oxidation reactions. Arch. Biochem. Biophys. 143:66-79.
34. 5 in the cytochrome P-450-dependent oxygenase system. Arch. Biochem. Biophys. 228:600-608.
35. Hosny, G., Roman, L. J., Mostafa, M. H., Masters, B. S. S. (1999). Characterization of purified, E. coli-expressed cytochrome P450 4A5. Arch. Biochem. Biophys. 366:199-206.
36. Huang, N., Pandey, A. V., Agrawal, V., Reardon, W., Lapunzina, P. D., Mowat, D., Jabs, E. W., Vliet, G. V., Sack, J., Flück, C. E., Miller, W. L. (2005). Diversity and function of mutations in p450 oxidoreductase in patients with Antley-Bixler syndrome and disordered steroidogenesis. Am. J. Hum. Genet. 76:729-749.
37. Hubbard, P. A., Shen, A. L., Paschke, R., Kasper, C. B., Kim, J. J. (2001). NADPH-cytochrome P450 oxidoreductase. Structural basis for hydride and electron transfer. J. Biol. Chem. 276:29163-29170.
38. 5 in a reconstituted N-demethylase system containing cytochrome P450. Biochem. Biophys. Res. Commun. 75:420-426.
39. 2 in reconstituted phospholipid vesicles. Biochem. Biophys. Res. Commun. 97:582-586.
40. 5 in microsomes. Arch. Biochem. Biophys. 325:265-269.
41. Johnson, E. F., Walker, D. L., Griffin, K. J., Clark, J. E., Okita, R. T., Muerhoff, A. S., Masters, B. S. S. (1990). Cloning and expression of three rabbit kidney cDNAs encoding lauric acid ω-hydroxylases. Biochemistry 29:873-879.
42. + reductase: prototype for a structurally novel flavoenzyme family. Science 251:60-66.
43. Kasper, C. B. (1971). Biochemical distinctions between the nuclear and microsomal membranes from rat hepatocytes. J. Biol. Chem. 246:577-581.
44. 5 in the biosynthesis of androgens by human CYP17. Arch. Biochem. Biophys. 317:343-347.
45. Kelley, R. I., Kratz, L. E., Glaser, R. L., Netzloff, M. L., Wolf, L. M., Jabs, E. W. (2002). Abnormal sterol metabolism in a patient with Antley-Bixler syndrome and ambiguous genitalia. Am. J. Med. Genet. 110:95-102.
46. Kondo, S., Sakaki, T., Ohkawa, H., Inouye, K. (1999). Electrostatic interaction between cytochrome P450 and NADPH-P450 reductase: comparison of mixed and fused systems consisting of rat cytochrome P450 1A1 and yeast NADPH-P450 reductase. Biochem. Biophys. Res. Commun. 257:273-278.
47. Kupfer, D., Miranda, G. K., Navarro, J., Piccolo, D. E., Theoharides, A. D. (1979). Effect of inducers and inhibitors of monooxygenase on the hydroxylation of prostaglandins in the guinea pig. Evidence for several monooxygenases catalyzing ω- and (ω-1)-hydroxylation. J. Biol. Chem. 254:10405-10414.
48. Kupfer, D., Navarro, J., Miranda, G. K., Theoharides, A. D. (1980). Metabolism of prostaglandins and xenobiotics by adrenal microsomal monooxygenase in the guinea pig. Arch. Biochem. Biophys. 205:297-307.
49. 1 by liver microsomal monooxygenase. Characteristics of the enzyme system in the guinea pig. J. Biol. Chem. 253:2804-2811.
50. Kuriyama, Y., Omura, T., Siekevitz, P., Palade, G. (1969). Effects of phenobarbital on the synthesis and degradation of the protein components of rat liver microsomal membranes. J. Biol. Chem. 244:2017-2026.
51. La Du, B. N., Gaudette, L., Trousof, N., Brodie, B. B. (1955). Enzymatic dealkylation of aminopyrine (Pyramidon) and other alkylamines. J. Biol. Chem. 214:741-752.
52. 5 reductase complex efficiently drives the entire sterol 14-demethylation (CYP51) reaction. FEBS Lett. 462:283-288.
53. 5. Biochem. J. 321:857-863.
54. 5: endocrinological and mechanistic implications. Biochem. J. 308:901-908.
55. 5. Arch. Biochem. Biophys. 268:152-160.
56. Loughran, P. A., Roman, L. J., Aitken, A. E., Miller, R. T., Masters, B. S. S. (2000). Identification of unique amino acids that modulate CYP4A7 activity. Biochemistry 39:15110-15120.
57. 5 effects vary with substrate. Arch. Biochem. Biophys. 385:311-321.
58. Lu, A. Y. H., Coon, M. J. (1968). Role of hemoprotein P-450 in fatty acid ω-hydroxylation in a soluble enzyme system from liver microsomes. J. Biol. Chem. 243:1331-1332.
59. 5 in the NADPH-supported cytochrome P-450-dependent hydroxylation of chlorobenzene. Biochem. Biophys. Res. Commun. 61:1348-1355.
60. Marx, J. L. (1995). The cytochrome P450's and their genes. Science 228:975-976.
61. Masters, B. S. S., Baron, J., Taylor, W. E., Isaacson, E. L., LoSpalluto, J. (1971a). Immunochemical studies on electron transport chains involving cytochrome P-450. I. Effects of antibodies to pig liver microsomal reduced triphosphopyridine nucleotide-cytochrome c reductase and the non-heme iron protein from bovine adrenocortical mitochondria. J. Biol. Chem. 246:4143-4150.
62. Masters, B. S. S., Nelson, E. B., Ziegler, D. M., Baron, J., Raj, P. P., Isaacson, E. L. (1971b). Immunochemical studies utilizing antibody to NADPH-cytochrome c reductase as a specific inhibitor of microsomal electron transport. Chem. Biol. Interact. 3:607-613.
63. 1 and lauric acid by pig kidney microsomes and a purified kidney cytochrome P-450. J. Biol. Chem. 256:5961-5964.
64. Omura, T., Sato, R. (1962). A new cytochrome in liver microsomes. J. Biol. Chem. 237:1375-1381.
65. Otto, D. M., Henderson, C. J., Carrie, D., Davey, M., Gunderson, T. E., Blomhoff, R., Adams, R. H., Tickle, C., Wolf, C. R. (2003). Identification of novel roles of the cytochrome p450 system in early embryogenesis: effects on vasculogenesis and retinoic acid homeostasis. Mol. Cell. Biol. 23:6103-6116.
66. Peterson, J. A., White, R. E., Yasukochi, Y., Coomes, M. L., O'Keeffe, D. H., Ebel, R. E., Masters, B. S. S., Ballou, D. P., Coon, M. J. (1977). Evidence that purified liver microsomal cytochrome P450 is a one-electron acceptor. J. Biol. Chem. 252:4431-4434.
67. Phillips, A. H., Langdon, R. G. (1962). Hepatic triphosphopyridine nucleotide-cytochrome c reductase: Isolation, characterization, and kinetic studies. J. Biol. Chem. 237:2652-2660.
68. Powell, W. S. (1978). ω-Oxidation of prostaglandins by lung and liver microsomes. Changes in enzyme activity induced by pregnancy, pseudopregnancy, and progesterone treatment. J. Biol. Chem. 253:6711-6716.
69. Powell, W. S., Solomon, S. (1978). Formation of 20-hydroxyprostaglandins by lungs of pregnant rabbits. J. Biol. Chem. 253:4609-4616.
70. Pursley, T. J., Blomquist, I. K., Abraham, J., Andersen, H. F., Bartley, J. A. (1996). Fluconazole-induced congenital anomalies in three infants. Clin. Infect. Dis. 22:336-340.
71. Reardon, W., Smith, A., Honour, J. W., Hindmarsh, P., Das, D., Rumsby, G., Nelson, I., Malcolm, S., Ades, L., Sillence, D., Kumar, D., DeLozier-Blanchet, C., McKee, S., Kelly, T., McKeehan, W. L., Baraitser, M., Winter, R. M. (2000). Evidence for digenic inheritance in some cases of Antley-Bixler syndrome? J. Med. Genet. 37:26-32.
72. Roman, L. J., Palmer, C. N. A., Clark, J. E., Muerhoff, A. S., Griffin, K. J., Johnson, E. F., Masters, B. S. S. (1993). Expression of rabbit cytochromes P4504A which catalyze the ω-hydroxylation of arachidonic acid, fatty acids and prostaglandins. Arch. Biochem. Biophys. 307:57-65.
73. Rossmann, M. G., Moras, D., Olsen, K. W. (1974). Chemical and biological evolution of nucleotide-binding proteins. Nature 250:194-199.
74. 5 in the oxidation of lauric acid by microsomes from kidney cortex and liver of rats. Life Sci. 14:35-46.
75. 5 in cytochrome P-450 enzymes. Adv. Exp. Med. Biol. 58:435-445.
76. Schachter, B. A., Nelson, E. B., Marver, H. S., Masters, B. S. S. (1972). Immunochemical evidence for an association of heme oxygenase with the microsomal electron transport system. J. Biol. Chem. 247:3601-3607.
77. Schinzel, A., Savoldelli, G., Briner, J., Sigg, P., Massini, C. (1983). Antley-Bixler syndrome in sisters: a term newborn and a prenatally diagnosed fetus. Am. J. Med. Genet. 14:139-147.
78. Serabjit-Singh, C. J., Albro, P. W., Robertson, I. G. C., Philpot, R. M. (1983). Interactions between xenobiotics that increase or decrease the levels of cytochrome P-450 isozymes in rabbit lung and liver. J. Biol. Chem. 258:12827-12834.
79. Shen, A. L., Kasper, C. B. (1995). Role of acidic residues in the interaction of NADPH-cytochrome P450 oxidoreductase with cytochrome P450 and cytochrome. c. J. Biol. Chem. 270:27475-27480.
80. Shen, A. L., O'Leary, K. A., Kasper, C. B. (2002). Association of multiple developmental defects and embryonic lethality with loss of microsomal NADPH-cytochrome P450 oxidoreductase. J. Biol. Chem. 277:6536-6541.
81. Strobel, H. W., Lu, A. Y. H., Heidema, J., Coon, M. J. (1970). Phosphatidylcholine requirement in the enzymatic reduction of hemoprotein P-450 and in fatty acid, hydrocarbon, and drug hydroxylation. J. Biol. Chem. 245:4851-4854.
82. Stromstedt, M., Keeney, D. S., Waterman, M. R., Paria, B. C., Conley, A. J., Dey, S. K. (1996). Pre-implantation mouse blastocysts fail to express CYP genes required for estrogen biosynthesis. Mol. Reprod. Dev. 43:428-436.
83. Suzuki, K., Kanda, Y., Sugiyama, K., Katoh, T., Wada, Y., Yasui, Y. (1987). Antley-Bixler syndrome in a sister and brother. Jpn. J. Hum. Genet. 32:247-252.
84. Truan, G., Epinat, J. C., Rougeulle, C., Cullin, C., Pompon, D. (1994). Cloning and characterization of a yeast cytochrome b5-encoding gene which suppresses ketoconazole hypersensitivity in a NADPH-P-450 reductase-deficient strain. Gene. 142:123-127.
85. 5. J. Biol. Chem. 257:11221-11229.
86. Wada, F., Shibata, H., Goto, M., Sakamoto, Y. (1968). Participation of the microsomal electraon transport system involving cytochrome P-450 in ω-oxidation of fatty acids. Biochim. Biophys. Acta. 162:518-524.
87. Wang, M., Roberts, D. L., Paschke, R., Shea, T. M., Masters, B. S. S., Kim, J. J. P. (1997). Three-dimensional structure of NADPH-cytochrome P450 reductase: Prototype for FMN- and FAD-containing enzymes. Proc. Nat. Acad. Sci. USA. 94:8411-8416.
88. 5 for oxidation by cytochrome P450. Methods in Enzymology 206:523-529.
89. 5 and the integrated microsomal electron transport system. In: Coon, M. J., Conney, A. W., Estabrook, R. W., Gelboin, H. V., Gillette, J. R., O'Brien, P. J., eds. Microsomes, Drug Oxidations, and Chemical Carcinogenesis. Vol. 1 New York: Academic Press. pp. 469-476.
90. 5 in the NADH-dependent hydroxylation of 3,4-benzpyrene by a reconstituted cytochrome P-448-containing system. Biochem. Biophys. Res. Commun. 58:516-522.
91. Williams, C. H., Jr., Kamin, H. (1962). Microsomal triphosphopyridine nucleotide-cytochrome c reductase of liver. J. Biol. Chem. 237:587-595.
92. PG-ω) purified from lungs of pregnant rabbits. J. Biol. Chem. 259:14600-14608.
93. Wu, L., Gu, J., Cui, H., Zhang, Q.-Y., Behr, M., Fang, C., Weng, Y., Kluetzman, K., Swiatek, P. J., Yang, W., Kaminskey, L., Ding, X. (2005). Transgenic mice with a hypomorphic NADPH-cytochrome P450 reductase gene: effects on development, reproduction, and microsomal cytochrome P450. J. Pharmacol. Exp. Ther. 312:35-43.
94. Wu, L., Gu, J., Weng, Y., Kluetzman, K., Swiatek, P., Behr, M., Zhang, Q. Y., Zhuo, X., Xie, Q., Ding, X. (2003). Conditional knockout of the mouse NADPH-cytochrome p450 reductase gene. Genesis. 36:177-181.
95. Yamamoto, S., Kusunose, E., Ogita, K., Kaku, M., Ichihara, K., Kusunose, M. (1984). Isolation of cytochrome P-450 highly active in prostaglandin omega-hydroxylation from lung microsomes of rabbits treated with progesterone. J. Biochem. 96:593-603.
96. 5. J. Biol. Chem. 271:27438-27444.
97. 5 in the oxidation of testosterone and nifedipine by recombinant cytochrome P450 3A4 and by human liver microsomes. Arch. Biochem. Biophys. 325:174-182.
98. Yasui, Y., Yamaguchi, A., Itoh, Y., Ueke, T., Sugiyama, K., Wada, Y. (1983). The first case of the Antley-Bixler syndrome with consanguinity in Japan. Jpn. J. Hum. Genet. 28:215.