The diversity and importance of microbial cytochromes P450

Cytochrome P450: Structure, Mechanism, and Biochemistry: Third edition

Volumn , Issue , 2005, Pages 585-617

  Kelly, Steven L ^a   Kelly, Diane E ^a   Jackson, Colin J ^a   Warrilow, Andrew G S ^a   Lamb, David C ^a  

^a SWANSEA UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84892288582     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/0-387-27447-2_13     Document Type: Chapter

References (171)

1. Klingenberg, M. (1958). Pigments of rat liver microsomes. Arch. Biochem. Biophys. 75, 376-386.
2. Omura, T. and R. Sato (1962). A new cytochrome in liver microsomes. J. Biol. Chem. 237, 1375-1376.
3. Estabrook, R. W., D. Y. Cooper, and O. Rosenthal (1963). The light reversible carbon monoxide inhibition of the steroid C21-hydroxylase system of the adrenal cortex. Biochem. Z. 338, 741.
4. Lu, A. Y. H., K. W. Junk, and M. J. Coon (1969). Resolution of the cytochrome P450 in fatty acid ω-hydroxylation system into three components. J. Biol. Chem. 243, 1331-1332.
5. Hanukoglu, I. (1992). Steroidogenic enzymes: Structure, function and regulation of expression. J. Steroid Biochem. Mol. Biol. 43, 779-804.
6. Lindenmeyer, A. and L. Smith (1964). Cytochromes and other pigments of bakers yeast grown aerobically and anaerobically. Biochem. Biophys. Acta. 93, 445-461.
7. Appleby, C. A. (1967). A soluble haemoprotein P450 from nitrogen-fixing rhizobium bacteroids. Biochem. Biophys. Acta. 147, 399-402.
8. Katagiri, M., B. N. Ganguli, and I. C. Gunsalus (1968). A soluble cytochrome P450 functional in methylene hydroxylation. J. Biol. Chem. 243, 3543-3546.
9. Tyson, C. A., J. D. Lipscomb, and I. C. Gunsalus (1972). The role of putidaredoxin and P450 cam in methylene hydroxylation. J. Biol. Chem. 247, 5777-5784.
10. Rheinwald, J. G., A. M. Chakrabarty, and I. C. Gunsalus (1973). A transmissible plasmid controlling camphor oxidation in Pseudomonas putida. Proc. Natl. Acad. Sci. USA 70, 885-889.
11. Sligar, S. G., P. G. Debrunner, J. D. Lipscomb, M. J. Namtvedt, and I. C. Gunsalus (1974). A role of the putidaredoxin COOH-terminus in P-450cam (cytochrome m) hydroxylations. Proc. Natl. Acad. Sci. USA 71, 3906-3910.
12. Koga, H., B. Rauchfuss, and I. C. Gunsalus (1985). P450cam gene cloning and expression in Pseudomonas putida and Escherichia coli. Biochem. Biophys. Res. Commun. 130, 412-417.
13. Narhi, L. O. and A. J. Fulco (1982). Phenobarbital induction of a soluble cytochrome P450 dependent fatty acid monooxygenase from Bacillus megaterium. J. Biol. Chem. 257, 2147-2150.
14. Kelly, S. L., D. C. Lamb, M. Cannieux, D. Greetham, C. J. Jackson, T. Marczylo et al. (2001). An old activity in the P450 superfamily (CYP51) and a new story of drugs and resistance. Biochem. Soc. Trans. 29, 122-128.
15. Nelson, D. R., L. Koymans, T. Kamataki, J. J. Stegeman, R. Feyereisen, D. J. Waxman et al. (1996). P450 superfamily: Update on new sequences, gene mapping, accession numbers and nomenclature. Pharmacogenetics 6, 1-42.
16. Kelly, S. L., D. C. Lamb, and D. E. Kelly (1999). Inhibitors of CYP51 as antifungal agents and resistance to azole antifungals. In (E. Arinc, J. B. Schenkman, and E. Hodgson (eds), Molecular and Applied Aspects of Oxidative Drug Metabolising Enzymes. Plenum, New York, pp. 157-172.
17. Szczebara, F. M., C. Chandelier, C. Villeret, A. Masurel, S. Bourot, C. Duport et al. (2003). Total biosynthesis of hydrocortisone from a simple carbon source. Nat. Biotechnol. 21, 143-149.
18. Rodriguez-Saiz, M., J. L. Barredo, M. A. Moreno, J. M. Fernandez-Canon, M. A. Penalva, and B. Diez (2001). Reduced function of a phenylacetateoxidising cytochrome P450 caused by strong genetic improvement in early phylogeny of penicillin-producing strains. J. Bact. 183, 5465-5471.
19. Mingot, J. M., M. A. Penalva, and J. M. Fernandez-Canon (1999). Disruption of phacA, an Aspergillus nidulans gene encoding a novel cytochrome P450 monooxygenase catalysing phenylacetate 2-hydroxylation results in penicillin overproduction. J. Biol. Chem. 274, 14545-14550.
20. Smith, K. E., F. Ahmed, and T. Antoniou (1993). Microbial transformation of steroids. Biochem. Soc. Trans. 21, 1077-1080.
21. Lupetti, A., R. Danesi, M. Campa, M. Del Tacca, and S. Kelly (2002). Molecular basis of resistance to azole antifungals. Trends Mol. Med. 8, 76-81.
22. Wen, L. P. and A. J. Fulco (1987). Cloning of the gene encoding a catalytically self-sufficient cytochrome P450 fatty-acid monooxygenase induced by barbiturates in Bacillus megaterium and its functional expression and regulation in heterologous (Escherichia coli) and homologous (Bacillus megaterium) hosts. J. Biol. Chem. 262, 6676-6682.
23. Park, S. Y., H. Shimizu, S. Adachi, A. Nakagawa, I. Tanaka, K. Nakahara et al. (1997). Crystal structure of nitric oxide reductase from denitrifying fungus Fusarium oxysporum. Nat. Struct. Biol. 4, 827-832.
24. Kelly, S. L., D. C. Lamb, C. J. Jackson, A. G. S. Warrilow, and D. E. Kelly (2003). The biodiversity of microbial cytochromes P450. Adv. Microb. Physiol. 47, 131-186.
25. Hawkes, D. B., G. W. Adams, A. L. Burlingame, P. R. O. De Montellano, and J. J. De Voss (2002). Cytochrome P450 (cin) (CYP176A1), isolation, expression and characterization. J. Biol. Chem. 277, 27725-27732.
26. Roberts, G. A., G. Grogan, A. Greter, S. L. Flitsch, and N. J. Turner (2002). Identification of a new class of cytochrome P450 from a Rhodococcus sp. J. Bact. 184, 3898-3908.
27. Jackson, C. J., D. C. Lamb, T. Marczylo, A. G. S. Warrilow, N. J. Manning, D. J. Lowe et al. (2002). A novel sterol 14α-demethylase/ ferredoxin fusion protein (MCCYP51FX) from Methylococcus capsulatus represents a new class of the cytochrome P450 superfamily. J. Biol. Chem. 277, 46959-46965.
28. Seth-Smith, H. M. B., S. J. Rosser, A. Basran, E. R. Travis, E. R. Dabbs, S. Nicklin et al. (2002). Cloning, sequencing and characterisation of the hexahydro-1, 3, 5-trinitro-1, 3, 5-triazine degradation gene cluster from Rhodococcus rhodochrous. Appl. Env. Microbiol. 68, 4764-4771.
29. De Mot, R. and A. H. Parret (2002). A novel class of self-sufficient cytochrome P450 monooxygenase in prokaryotes. Trends Microbiol. 10, 502-508.
30. Gonzalez, F. J. and D. W. Nebert (1990). Evolution of the P450 gene superfamily: Animal-plant warfare, molecular drive and human genetic differences in drug oxidation. Trends Genet. 6, 182-186.
31. Nelson, D. R. (1999). Cytochrome P450 and the individuality of species. Arch. Biochem. Biophys. 369, 1-10.
32. Yoshida, Y, Y. Aoyama, M. Noshiro, and O. Gotoh (2000). Sterol 14-demethylase P450 (CYP51) provides a breakthrough for the discussion of the evolution of cytochrome P450 gene superfamily. Biochem. Biophys. Res. Commun. 213, 799-804.
33. Jackson, C. J., D. C. Lamb, T. H. Marczylo, J. E. Parker, N. J. Manning, D. E. Kelly et al. (2003). Conservation and cloning of CYP51, a sterol 14ademethylase from Mycobacterium smegmatis. Biochem. Biophys. Res. Commun. 307, 558-563.
34. Stoke, J. E. and J. J. De Voss (2000). Expression, purification and characterisation of biol: A carboncarbon bond cleaving cytochrome P450 involved in biotin biosynthesis in Bacillus subtilis. Arch. Biochem. Biophys. 384, 351-360.
35. Kalb, V. F., C. W. Woods, T. G. Turi, C. R. Dey, T. R. Sutter, and J. C. Loper, (1987). Primary structure of P450 lanosterol demethylase gene from Sacchaaromyces cerevisiae. DNA 6, 529-537.
36. Aoyama, Y., Y. Funae, M. Noshiro, T. Horiuchi, and Y. Yoshida (1994). Occurence of a P450 showing high homology to yeast lanosterol 14-demethylase (P45014DM) in the rat liver. Biochem. Biophys. Res. Commun. 201, 1320-1326.
37. Stromstedt, M., D. Rozman, and M. R. Waterman (1996). The ubiquitously expressed human CYP51 encodes lanosterol 14-demethylase, a cytochrome P450 whose expression is regulated by oxysterols. Arch. Biochem. Biophys. 329, 73-81.
38. Bak, S., R. A. Kahn, C. E. Olsen, and B. Halkier (1997). Cloning and expression in E.coli of the obtusifoliol of Sorghum bicolor (L.) Moench, a cytochrome P450 orthologous to the sterol 14α-demethylases (CYP51) from mammals and fungi. Plant J. 11, 191-201.
39. Lamb, D. C., D. E. Kelly, and S. L. Kelly (1998). Molecular diversity of sterol 14α-demethylase substrates in plants, fungi and humans. FEBS Lett. 425, 263-265.
40. Wickramashighe, R. H. and C. A. Villee (1975). Early role during chemical evolution for cytochrome P450 in oxygen detoxification. Nature 256, 509-510.
41. Godzina, S. M., M. A. Lovato, M. M. Meyer, K. A. Foster, W. K. Wilson, W. Gu et al. (2000). Cloning and characterisation of the Dictyostelium discoideum. Lipids 35, 249-255.
42. Joubert, B. M., F. S. Buckner, and S. P. T. Matsuda (2001). Trypanosome and animal lanosterol synthase use different catalytic motifs. Org. Lett. 3, 1957-1960.
43. Bellamine, A., A. T. Mangla, W. D. Nes, and M. R. Waterman (1999). Characterisation and catalytic properties of the sterol 14α-demethylase from Mycobacterium tuberculosis. Proc. Natl. Acad. Sci. USA 96, 8937-8942.
44. Podust, L. M., T. L. Poulos, and M. R. Waterman (2001). Crystal structure cytochrome P450 14α-sterol demethylase from Mycobacterium tuberculosis in complex with azole inhibitors. Proc. Natl. Acad. Sci. USA 98, 3068-3073.
45. Bird, C. W., J. M. Lynch, F. J. Pirt, W. W. Reid, C. J. W. Brooks, and B. S. Middleditch (1971). Steroids and squalene in Methylococcus capsulatus grown on methane. Nature 230, 473-474.
46. Bode, H. B., B. Zeggel, B. Silakowski, S. C. Wenzel, H. Reichenbach, and R. Muller (2003). Steroid biosynthesis in prokaryotes: Identification of myxobacterial steroids and cloning of the first bacterial 2, 3 (S)-oxidosqualene cyclase from the myxobacterium Stigmatella aurantiaca. Mol. Microbiol. 47, 471-481.
47. Buckner, F. S., A. J. Wilson, T. C. White, and W. C. Van Voorhis (1998). Induction of resistance to azole drugs in Trypanosoma cruzi. Antimicrob. Agents Chemother. 42, 3245-3250.
48. Salimova, E., A. Boschetti, W. Eichenberger, and L. Lutova (1999). Sterol mutants of Chlamydomonas reinhardtii: Characterisation of three strains deficient in C24 (28) reductase. Plant Physiol. Biochem. 37, 241-249.
49. Kelly, S. L., D. C. Lamb, and D. E. Kelly (1997). Sterol 22-desaturase, cytochrome P450 61, possesses activity in xenobiotic metabolism FEBS Lett. 412, 233-235.
50. Lamb, D. C, K. Fowler, T. Kieser, N. J. Manning, L. M. Podust, M. R. Waterman et al. (2002). Sterol 14α-demethylase activity in Streptomyces coelicolor A3 (2) is associated with an unusual member of the CYP51 gene family. Biochem. J. 364, 555-562.
51. Jackson, C. J., D. C. Lamb, D. E. Kelly, and S. L. Kelly (2000). Bactericidal and inhibitory effects of azole antifungal compounds on Mycobacterium smegmatis. FEMS Lett. 192, 159-162.
52. Guardiola-Diaz, H. M., L. A. Foster, D. Mushrush, and A. D. N. Vaz (2001). Azole-binding to a novel cytochrome P450 from Mycobacterium tuberculosis: Implications for treatment of tuberculosis. Biochem. Pharmacol. 61, 1463-1470.
53. McLean, K. J., M. R. Cheeseman, S. L. Rivers, A. Richmond, D. Leys, S. K. Chapman et al. (2002). Expression, purification and spectroscopic characterisation of the cytochrome P450 CYP121 from Mycobacterium tuberculosis. J. Inorg. Biochem. 91, 527-541.
54. Cole, S. T., K. Eiglmeier, J. Parkhill, K. D. James, N. R. Thomson, P. R. Wheeler et al. (2001). Massive gene decay in leprosy bacillus. Nature 409, 1007-1011.
55. Tang, L., S. Shah, L. Chung, J. Carney, L. Katz, C. Khosla et al. (2000). Cloning and expression of the epothilone gene cluster. Science 287, 640-642.
56. August, P. R., L. Tang, Y. J. Yoon, S. Ning, R. Muller, T-W Yu et al. (1998). Biosynthesis of the ansamycin antibiotic rifamycin: Deductions from the molecular analysis of the rif biosynthetic cluster of Amycolatopsis mediteranei S699. Chem. Biol. 5, 69-79.
57. Poulos, T. L., B. C. Finzel, I. C. Gunsalus, G. C. Wagner, and J. Kraut (1985). The 2.6A crystal structure of Pseudomonas putida cytochrome P450. J. Biol. Chem. 260, 16122-16130.
58. Poulos, T. L., B. C. Finzel, and A. J. Howard (1987). High-resolution crystal structure of cytochrome P450cam. J. Mol. Biol. 195, 687-700.
59. Peterson, J. A., J. Y. Lu, J. Geisselsoder, S. Graham Lorence, C. Carmona, F. Witney et al. (1992). Cytochrome P450 terp-isolation and purification of the protein and cloning and sequencing of its operon. J. Biol. Chem. 267, 14193-14203.
60. Nagy, I., F. Compernolle, K. Ghys, J. Van Der Leyden, and R. Demot (1995). A single cytochrome P450 system is involved in degradation of the herbicides EPTC (S-ethyl dipropylthiocarbamate) and atrazine by Rhodococcus sp. strain NI86/21. J. Bact. 61, 2056-2060.
61. O'Keefe, D. P., J. M. Tepperman, C. Dean, K. J. Leto, D. L. Erbes, and J. T. O'Dell (1994). Plant expression of a bacterial cytochrome P450 that catalyzes activation of a sulfonylurea pro-herbicide. Plant Physiol. 105, 473-482.
62. Ruettinger, R. T. and A. J. Fulco (1981). Epoxidation of unsaturated fatty acids by a soluble cytochrome P-450-dependent system from Bacillus megaterium. J. Biol. Chem. 256, 5728-5734.
63. Narhi, L. O. and A. J. Fulco (1986). Characterization of a catalytically self-sufficient 119, 000-dalton cytochrome P-450 monooxygenase induced by barbiturates in Bacillus megaterium. J. Biol. Chem. 261, 7160-7169.
64. Narhi, L. O. and A. J. Fulco (1987). Identification and characterization of two functional domains in cytochrome P-450BM-3, a catalytically self-sufficient monooxygenase induced by barbiturates in Bacillus megaterium. J. Biol. Chem. 262, 6683-6690.
65. Ravichandran, K. G., S. S. Boddupalli, C. A. Hasermann, J. A. Peterson, and J. Deisenhofer (1993). Crystal structure of hemoprotein domain of P450BM-3, a prototype for microsomal P450's. Science 261, 731-736.
66. Munro, A. W. (1994). The role of Tryptophan 97 of cytochrome P450 BM3 from Bacillus megaterium in catalytic function. Biochem. J. 303, 423-428.
67. Yeom, H., S. G. Sligar, H. Y. Li, T. L. Poulos, and A. J. Fulco (1995). The role of Thr268 in oxygen activation in cytochrome P450 BM3. Biochemistry 34, 14733-14740.
68. Klein, M. L. and A. J. Fulco (1993). Critical residues involved in FMN binding and catalytic activity in cytochrome P450BM3. J. Biol. Chem. 268, 7553-7561.
69. Yano, J. K., L. S. Koo, D. J. Schuller, H. Li, P. R. Ortiz De Montellano, and T. L. Poulos (2000). Crystal structure of a thermophilic cytochrome P450 from the archaeon Sulfolobus solfataricus. J. Biol. Chem. 275, 31086-31092.
70. Yano, J. K., F. Blasco, H. Li, R. D. Schmid, A. Henne, and T. L. Poulos (2003). Preliminary characterization and crystal structure of a thermostable cytochrome P450 from Thermus thermophilus. J. Biol. Chem. 278, 608-616.
71. Cole, S. T., R. Brosch, J. Parkhill, T. Gamier, C. Churcher, D. Harris et al. (1998). Deciphering the biology of Mycobacterium tuberculosis from the complete genome sequence. Nature 393, 537-554.
72. Bentley, S. D., K. F. Chater, A. M. Cerdeno-Tarraga, G. L. Challis, N. R. Thomson, K. D. James et al. (2002). Complete sequence of the model actinomyctete Streptomyces coelicolor A3 (2). Nature 417, 141-147.
73. Lamb, D. C., T. Skaug, H.-L. Song, C. J. Jackson, L. Podust, M. R. Waterman et al. (2002). The cytochrome P450 complement (CYPome) of Streptomyces coelicolor A3 (2). J. Biol. Chem. 277, 24000-24005.
74. Lamb, DC, H. Ikeda, D. R. Nelson, J. Ishikawa, T. Skaug, Jackson C. J. et al. (2003). Cytochrome P450 complement of the avermectin-producer Strepto-myces avermitilis and comparison to that of Streptomyces coelicolor A3 (2). Biochem. Biophys. Res. Commun. 307, 610-619.
75. Sariaslani, F. S. and J. P. Rosazza (1983). Novel biotransformations of 7-ethoxycoumarin by Streptomyces griseus. Appl. Environ. Microbiol. 46, 468-474.
76. Sariaslani, F. S. and J. P. Rosazza (1983). Microbial transformation of natural anti-tumor agents-products of rotenone and dihydrorotenone transformation. Appl. Environ. Microbiol. 49, 451-452.
77. Trower, M. K., R. Lenstra, C. Omer, S. E. Buchholz, and F. S. Sariaslani (1992). Cloning, nucleotide sequence determination and expression of the genes encoding cytochrome P450soy (SOYC) and ferredoxinSOY (SOYC) from Steptomyces griseus. Mol. Microbiol. 6, 2125-2134.
78. O'Keefe, D. P., S. M. C. Lau, and P. A. Harder (1993). Efficiency and substrate-specificity of Streptomyces griseolus cytochrome P450SU1 and cytochrome P450SU2 monooxygenase reactions. Biochem. Soc. Trans. 21, 1073-1077.
79. Poupin, P., V. Ducrocq, S. Hallier-Soulier, and N. Truffeut (1999). Cloning and characterisation of the genes encoding a cytochrome P450 (PipA) involved in piperidine and pyrrolidine utilisation and its regulatory protein (PipR) in Mycobacterium smegmatis mc (2) 155. J. Bacteriol. 181, 3419-3426.
80. Cannell, R. J. P., A. R. Knaggs, M. J. Dawson, G. R. Manchee, P. J. Eddershaw, I. Waterhouse et al. (1995). Microbial biotransformation of the angiotensin II antagonist GR117289 by Streptomyces rimosus to identify a mammalian metabolite. Drug Metab. Disp. 23, 724-729.
81. Berrie, JR., R. A. D. Williams, and K. E. Smith (1999). Microbial transformations of steroids-XI. Progesterone transformation by Streptomyces roseo chromogenes-purification and characterisation of the 16 alpha-hydroxylase system. J. Steroid Biochem. 71, 153-165.
82. Ito, S., T. Hata, I. Watanabe, T. Matsuoka, and N. Serizawa (1997). Crystal structure of cytochrome P450sca from Streptomyces carbophilus involved in production of pravastatin, a cholesterol lowering drug. FASEB J. 11, 36.
83. Ikeda, H., J. Ishikawa, A. Hanamoto, M. Shinose, H. Kikuchi, T. Shiba et al. (2003). Complete genome sequence and comparative analysis of the industrial microorganisms Streptomyces avermitilis Organism. Nat. Biotechnol. 21, 526-531.
84. Podust, L. M., Y. Kim, M. Arase, B. A. Neely, B. J. Beck, H. Bach et al. (2003). The 1.92-angstrom structure of Streptomyces coelicolor A3 (2) CYP154C1-a new monooxygenase that functionalises macrolide ring systems. J. Biol. Chem. 278, 12214-12221.
85. Komatsu, M., Y. Kuwara, A. Hiroishi, K. Hosono, T. Beppu, and K. Ueda (2003). Cloning of the conserved regulatory operon by its aerial mycelium-inducing activity in an amfR mutant of Streptomyces griseus. Gene 306, 79-89.
86. Briza, P., M. Eckerstorfer, and M. Breitenbach (1994). The sporulation-specific enzymes encoded by the DIT1 and DIT2 genes catalyze a two-step reaction leading to a soluble LL-dityrosine-containing precursor of the yeast spore wall. Proc. Natl. Acad. Sci. USA 91, 4524-4528.
87. Kelly, S. L., D. C. Lamb, A. J. Corran, B. C. Baldwin, L. W. Parks, and D. E. Kelly (1995). Purification and reconstitution of activity of Saccharomyces cerevisiae P450 61, a sterol 22-desaturase. FEBS Lett. 377, 217-220.
88. Smail, E. H., P. Briza, A. Panagos, and L. Berenfeld (1995). Candida albicans cell walls contain the fluorescent cross-linking amino acid dityrosine. Inf. Immun. 63, 4078-4083.
89. Masaphy, S., D. Levanon, Y. Henis, K. Venkateswarlu, and S. L. Kelly (1996). Evidence for cytochrome P450 and P450-mediated benzo (a) pyrene hydroxylation in the white-rot fungus Phanerochaete chrysosporium. FEMS Lett. 135, 51-55.
90. Kullman, S. W. and F. Matsumura (1997). Identification of a novel cytochrome P-450 gene from the white-rot fungus Phanerochaete chrysosporium. Appl. Environ. Microbiol. 63, 2741-2746.
91. Yadav, J. S. and J. C. Loper (2000). Cytochrome P450 oxidoreductase gene and its differentially terminated cDNAs from the white-rot fungus Phanerochaete chrysosporium. Curr. Genet. 37, 65-73.
92. Warrilow, A. G. S., D. C. Lamb, D. E. Kelly, and S. L. Kelly (2002). Phanerochaete chrysosporium NADPH-cytochrome P450 reductase kinetic mechanism. Biochem. Biophys. Res. Commun. 299, 189-195.
93. Breskvar, K., B. Cresnar, and T. Hudnik-Plevnik (1987). Resolution and reconstitution of cytochrome P450 containing steroid hydroxylation system of Rhizopus nigricans. J. Steroid Biochem. 14, 395-399.
94. Masaphy, S., D. C. Lamb, and S. L. Kelly (1999). Purification and characterization of a benzo (a) pyrene hydroxylase from Pleurotus pulmonarius. Biochem. Biophys. Res. Commun. 266, 326-329.
95. Lebeault, J. M., E. T. Lode, and M. J. Coon (1971). Fatty acid and hydrocarbon hydroxylation in yeast: Role of cytochrome P450 in Candida tropicalis. Biochem. Biophys. Res. Commun. 42, 413-419.
96. Sanglard, D. and J. C. Loper (1989). Characterisation of the alkane-inducible cytochrome P450 (P450ALK) gene from the yeast Candida tropicalis-identification of a new P450-gene family, Gene 76, 121-136.
97. Ohkuma, M., T. Zimmer, T. Iida, W. H. Schunck, A. Ohta, and M. Takagi (1998). Isozyme function of n-alkane-inducible cytochromes P450 in Candida maltosa revealed by sequential gene disruption. J. Biol. Chem. 273, 3948-3953.
98. Iida, T., A. Ohta, and M. Takagi (1998). Cloning and characterisation of an n-alkane inducible cytochrome P450 gene essential for n-decane assimilation by Yarrowia lipolytica,. Yeast 14, 1387-1397.
99. Van Gorcom, R. F., J. G. Boschloo, A. Kuijvenhoven, J. Lange, A. J. Van Vark, C. J. Bos et al. (1990). Isolation and molecular characterisation of the benzoate para-hydroxylase gene (bphA) of Aspergillus niger: A member of a new gene family of the cytochrome P450 superfamily. Mol. Gen. Genet. 223, 192-197.
100. Attar, R. M., E. Grotewold, G. E. Taccioli, G. O. Aisemberg, H. N. Torres, and N. D. Judewicz (1989). A cycloheximide-inducible gene of Neurospora crassa belongs to the cytochrome P450 superfamily. Nucleic Acids Res. 17, 7535-7536.
101. Han, Y. N., X. G. Liu, U. Benny, H. C. Kistler, and H. D. Van Etten (2001). Genes determining pathogenicity to pea are clustered on a supernumerary chromosome in the fungal plant pathogen Nectria haematococca. Plant J. 25, 305-314.
102. Hata, S., T. Nishino, M. Komori, and H. Katsuki (1981). Involvement of cytochrome P-450 in delta 22-desaturation in ergosterol biosynthesis of yeast. Biochem. Biophys. Res. Commun. 103, 272-277.
103. Skaggs, B. A., J. F. Alexander, C. A. Pierson, K. S. Schweitzer, K. T. Chun, C. Koegel et al. (1996). Cloning and characterization of the Saccharomyces cerevisiae C-22 sterol desaturase gene, encoding a second cytochrome P-450 involved in ergosterol biosynthesis. Gene 169, 105-109.
104. Kelly, S. L., D. C. Lamb, B. C. Baldwin, A. J. Corran, and D. E. Kelly (1997). Characterisation of Saccharomyces cerevisiae CYP61, a sterol delta 22-desaturase, and inhibition by azole antifungal agents. J. Biol. Chem. 272, 9986-9988.
105. Noda, H. and Y. Koizumi (2003). Sterol biosynthesis by symbiotes: Cytochrome P450 sterol C5-desaturase genes from yeastlike symbiotes of rice planthoppers and anobiid beetles. Insect Biochem. Mol. Biol. 33, 649-658.
106. Hohn, T. M., A. E. Desjardins, and S. P. McCormick (1995). The TRI4 gene of Fusarium sporotrichoides encodes a cytochrome P450 monooxygenase involved in trichothene biosynthesis. Mol. Gen. Genet. 248, 95-102.
107. Yu, J. J., P. K. Chang, K. C. Ehrlich, B. Montalbano, J. M. Dyer, D. Bhatnagar et al. (1998). Characterisation of the critical amino acids of an Aspergillus parasiticus cytochrome P450 monooxygenase encoded by ordA that is involved in the biosynthesis of aflatoxins B-l, G (l), B-2 and G (2). Appl. Env. Microbiol. 64, 4834-4841.
108. Yu, X, P. K. Chang, D. Bhatnagar, and T. E. Cleveland (2000). Genes encoding cytochrome P450 and monooxygenase enzymes define one end of the aflatoxin pathway gene cluster in Aspergillus parasiticus. Appl. Micro. Biotech. 53, 583-590.
109. Tudzynski, B., P. Hedden, E. Carrera, and P. Gaskin (2001). The P450-4 gene of Gibberella fujikuroi encodes ent-kaurene oxidase in the gibberellin biosynthesis pathway App. Environ. Microbiol. 67, 3514-3522.
110. Young, C, L. McMillan, E. Telfer, and B. Scott (2001). Molecular cloning and genetic analysis of an indole-diterpene gene cluster from Penicillium paxilli. Mol. Microbiol. 39, 754-764.
111. Kitazume, T., N. Takaya, N. Nakayama, and H. Shoun (2000). Fusarium oxysporum fatty acid subterminal hydroxylase (CYP505) is a membranebound counterpart of Bacillus megaterium P450BM3. J. Biol. Chem. 275, 39734-39740.
112. Lamb, D. C., D. E. Kelly, and S. L. Kelly (1999). Molecular aspects of azole antifungal action and resistance. Drug Resist. Updates 2, 90-402.
113. Odds, F. C. (1996). Antifungal therapy. in C. C. Kibbler, D. W. R. Mackenzie, and F. C. Odds (eds), Principles and Practise of Clinical Mycology, John Wiley & Sons, Chichester. pp. 1-6.
114. Ragsdale, N. N. and H. D. Sisler (1972). Mode of action of triarimol in Ustilago maydis. Biochem. Biophys. Res. Commun. 46, 2048-2053.
115. Marriott, M. (1980). Inhibition of sterol biosynthesis in Candida albicans by imidazole-containing antifungals. J. Gen. Microbiol. 117, 253-255.
116. Alexander, K., M. Akhtar, R. B. Boar, J. F. McGhie, and D. H. R. Barton (1972). The removal of the 32-carbon atom as formic acid in cholesterol biosynthesis. J. Chem. Soc. Chem. Commun. 383-385.
117. Aoyama, Y., Y. Yoshida, and R. Sato (1984). Yeast cytochrome P450 catalysing lanosterol 14α-demethylation. II. Lanosterol metabolism by purified P45014DM and by intact microsomes. J. Biol. Chem. 259, 1661-1666.
118. Aoyama, Y., Y. Yoshida, Y. Sonoda, and Y. Sato (1987). Metabolism of 32-hydroxy-24, 25-dihydrolanosterol by purified cytochrome P45014DM from yeast: Evidence for the contribution of the cytochrome to the whole process of lanosterol 14α-demethylation. J. Biol. Chem. 262, 1239-1243.
119. Aoyama, Y., Y. Yoshida, Y. Sonoda, and Y. Sato (1989). Deformylation of 32-hydroxy-24, 25-dihydrolanosterol by purified cytochrome P45014DM (lanosterol 14α-demethylase) from yeast: Evidence confirming the intermediate step of lanosterol 14α-demethylation. J. Biol. Chem. 264, 18502-18505.
120. Akhtar, M., K. Alexander, R. B. Boar, J. F. McGhie, and D. H. R. Barton (1978). Chemical and enzymic studies on the characterisation of intermediates during the removal of the 14α methyl group in cholesterol biosynthesis. Biochem. J. 169, 449-463.
121. Shyadehi, A. Z., D. C. Lamb, S. L. Kelly, D. E. Kelly, W. H. Schunck, and J. N. Wright et al. (1996). The mechanism of the acyl-carbon bond cleavage reaction catalyzed by recombinant sterol 14α-demethylase of Candida albicans (other names are: Lanosterol 14 alpha-demethylase, P-45014DM, and CYP51). J. Biol. Chem. 271, 12445-12450.
122. King, D. J., M. R. Azari, and A. Wiseman (1984). Studies on the properties of highly purified cyt. P448 and its dependent activity benzxo (a) pyrene hydroxylase from S. cerevisiae. Xenobiotica 14, 187-206.
123. Callen, D. F. and R. M. Philpot (1977). Cytochrome P450 and activation of promutagens in Saccharomyces cerevisiae. Mutat. Res. 55, 153-163.
124. Kelly, D. and J. M. Parry (1983). Metabolic activation of cytochrome P450/P448 in the yeast Saccharomyces cerevisiae. Mutat. Res. 108, 147-159.
125. Kelly, S. L., D. C. Lamb, B. C. Baldwin, and D. E. Kelly (1993). Benzo[a]pyrene activity in yeast is mediated by P450 other than sterol 14α-demethylase. Biochem. Biophys. Res. Commun. 197, 428-432.
126. Watson, P. F., M. E. Rose, S. W. Ellis, H. England, and S. L. Kelly (1989). Defective sterol C5-6 desaturation and azole resistance: A new hypothesis for the mode of action of azole antifungals. Biochem. Biophys. Res. Commun. 164, 1170-1175.
127. Kelly, S. L., A. Arnoldi, and D. E. Kelly (1993). Molecular genetic analysis of azole antifungal mode of action. Biochem. Soc. Trans. 21, 1034-1038.
128. Bard, M., N. D. Lees, T. Turi, D. Craft, L. Cofrin, R. Barbuch et al. (1993). Sterol synthesis and viability of ERG 11 (cytochrome P450 lanosterol demethylase) mutations in Saccharomyces cerevisiae and Candida albicans. Lipids 28, 963-967.
129. Kelly, S. L., D. C. Lamb, D. E. Kelly, J. Loeffler, and H. Einsele (1996). Resistance to fluconazole in Candida albicans from AIDS patients involving cross-resistance to amphotericin. Lancet 348, 1523-1524.
130. Nolte, F. S., T. Parkinson, D. J. Falconer, S. Dix, J. Williams, C. Gilmore et al. (1997). Isolation and characterisation of fluconazole and amphotericin B-resistant Candida albicans from blood of two patients with leukaemia Antimicrob. Agents Chemother. 44, 196-199.
131. Gachotte, D., C. A. Pierson, N. D. Lees, R. Barbuch, C. Koegel, and M. Bard (1997). A yeast sterol auxotroph (erg25) is rescued by addition of azole antifungals and reduced levels of heme. Proc. Natl. Acad. Sci. USA, 94, 11173-11178.
132. Nes, D. W., G. G. Janssen, F. G. Cromley, M. Kalinowska, and T. Akihisa (1993). The structural requirements of sterols for membrane function in Saccharomyces cerevisiae. Arch. Biochem. Biophys. 300, 724-733.
133. Bammert, G. F. and J. M. Fostel (2000). Genomewide expression patterns in Saccharomyces cerevisiae: Comparison of drug treatments and genetic alterations affecting biosynthesis of ergosterol. Antimicrob. Agents Chemother. 44, 1255-1263.
134. De Backer, M. D., T. Ilyina, X. Ma, S. Vandoninck, W. H. M. Luyten, and H. Van Den Bossche (2001). Genomic profiling of the response of Candida albicans to itraconazole treatment using a DNA microarray. Antimicrob. Agents Chemother. 45, 1660-1670.
135. Black, S. D. and M. J. Coon (1982). Structural features of liver microsomal NADPH-cytochrome P450 reductase; hydrophobic domain, hydrophilic domain and connecting region. J. Biol. Chem. 257, 5929-5938.
136. Sutter, T. C. and J. C. Loper (1989). Disruption of the Saccharomyces cerevisiae gene for NADPH-cytochrome P450 reductase causes increased sensitivity to ketoconazole. Biochem. Biophys. Res. Commun. 160, 1257-1266.
137. Goffeau, A., B. G. Barrell, H. Bussey, R. W. Davis, B. Dujon, H. Feldman et al. (1996). Life with 6000 genes. Science 274, 563-567.
138. Venkateswarlu, K., D. C. Lamb, D. E. Kelly, N. J. Manning, and S. L. Kelly (1998). The N-terminal membrane domain of yeast NADPH-cytochrome P450 (CYP) oxidoreductase is not required for catalytic activity in sterol biosynthesis or in reconstitution of CYP activity. J. Biol. Chem. 273, 4492-4496.
139. 5 reductase complex efficiently drives the entire sterol 14-demethylation (CYP51) reaction. FEBS Lett. 462, 283-288.
140. Gonczy, P., C. Eecheverri, K. Oegema, A. Coulson, S. J. M. Jones R. R. Copley et al. (2000). Functional genomic analysis of cell division in C. elegans using RNAi of genes on chromosome III. Nature 408, 331-336.
141. Shen, A. L., K. A. O'Leary, and C. B. Kasper (2002). Association of multiple developmental defects and embryonic lethality with loss of microsomal NADPH-cytochrome P450 oxidoreductase. J. Biol. Chem. 277, 6536-6541.
142. Lamb, D. C, D. E. Kelly, K. Venkateswarlu, N. J. Manning, H. F. J. Bligh, W. H. Shunck et al. (1999). Generation of a complete, soluble and catalytically active sterol 14α-demethylase-reductase complex. Biochemistry 38, 8733-8738.
143. Yoshida, Y. (1988). Cytochrome P450 of fungi: Primary target for azole antifungal agents. In M. R. McGinnis (ed.), Current topics in mycology, Springer-Verlag, New York, p. 388.
144. Wilkinson, C. F., K. Hetnarski, and T. O. Yellin (1972). Imidazole derivatives-a new class of microsomal enzyme inhibitors. Biochem. Pharmacol. 21, 3187-3192.
145. Aoyama, Y., Y. Yoshida, S. Hata, T. Nishino, and H. Katsuki (1983). Buthiobate: A potent inhibitor for yeast cytochrome P450 catalysing 14α-demethylation of lanosterol. Biochem. Biophys. Res. Commun. 115, 642-647.
146. Lamb, D. C., D. E. Kelly, M. R. Waterman, M. Stromstedt, D. Rozman, and S. L. Kelly (1999). Characteristics of the heterologously expressed human lanosterol 14α-demethylase (other names: P45014DM, CYP51, P45051) and inhibition of the purified human and Candida albicans CYP51 with azole antifungal agents. Yeast 15, 755-763.
147. Lamb, D. C, M. Cannieux, A. G. S. Warrilow, S. Bak, R. A. Kahn and N. J. Manning (2001). Plant sterol 14 α-demethylase affinity for azole fungicides. Biochem. Biophys. Res. Commun. 284, 845-849.
148. Kakeya, H., Y. Miyazaki, H. Miyazaki, K. Nyswaner, B. Grimberg, and J. E. Bennett (2000). Genetic analysis of azole resistance in the Darlington strain of Candida albicans. Antimicrob. Agents Chemother. 44, 2985-2990.
149. Venkateswarlu, K., D. W. Denning, N. J. Manning, and S. L. Kelly (1995). Resistance to fluconazole in Candida albicans from AIDS patients correlated with reduced intracellular accumulation of the drug. FEMS Microbiol. Lett. 131, 337-341.
150. Sanglard, D., K. Kuchler, F. Ischer, J-L. Pagani, M. Monod and J. Bille (1995). Mechanisms of resistance to azole antifungal agents in Candida albicans from AIDS patients involve specific multi-drug transporters. Antimicrob. Agents Chemother. 39, 2378-2386.
151. Sanglard, D., F. Ischer, M. Monod, and J. Bille (1997). Cloning of Candida albicans genes conferring resistance to azole antifungal agents: Characterisation of CDR2, a new multidrug ABC transporter gene. Microbiology 143, 405-416.
152. Sanglard, D., F. Ischer, L. Koymans, and J. Bille (1998). Amino-acid substitutions in the cytochrome P450 lanosterol 14α-demethylase (CYP51A1) from azole resistant Candida albicans clinical isolates contribute to resistance to azole antifungal agents. Antimicrob. Agents Chemother. 42, 241-253.
153. White, T. C. (1997). Increased mRNA levels of ERG 16, CDR and MDR1 correlate with increases in azole resistance in Candida albicans isolates from an HIV-infected patient. Antimicrob, Agents Chemother. 41, 1482-1487.
154. Franz, R., M. Ruhnke, D. C. Lamb, S. L. Kelly, and J. Morschhäuser (1998). Multiple molecular mechanisms contribute to a stepwise development of fluconazole resistance in clinical Candida albicans strains. Antimicrob. Agents Chemother. 42, 3065-3072.
155. Hamamoto, H., K. Hasegawa, R. Nakaune, Y. J. Lee, Y. Makizumi, K. Akutsu et al. (2000). Tandem repeat of a transcriptional enhancer upstream of the sterol 14alpha-demethylase gene (CYP51) in Penicillium digitatum Appl. Environ. Microbiol. 66, 3421-3426.
156. Mellado, E., T. M. Diaz-Guerra, M. Cuenca-Estrella, and J. L. Rodriguez-Tudela (2001). Identification of two different 14a sterol demethylase-related genes (cyp51A and cyp51B) in Aspergillus fumigatus and other aspergillus species. J. Clin. Microbiol. 39, 2431-2438.
157. Denning, D. W., K. Venkateswarlu, K. L. Oakley, M. J. Anderson, N. J. Manning, D. A. Stevens et al. (1997). Itraconazole resistance in Aspergillus fumigatus. Antimicrob. Agents Chemother. 41, 1364-1368.
158. 14DM: Complete primary structures deduced from cloned DNAs. Biochem. Biophys. Res. Commun. 155, 317-323.
159. Van Den Bossche, H., P. Marichal, J. Gorens, D. Bellens, H. Moereels, and P. Janssen (1990). Mutation in cytochrome P450 dependent 14a-demethylase results in decreased affinity for azole antifungals. Biochem. Soc. Trans. 18, 56-59.
160. Lamb, D. C, D. E. Kelly, W. H. Schunck, A. Z. Shyadehi, M. Akhtar, D. J. Lowe et al. (1997). The mutation T315A in Candida albicans sterol 14ademethylase causes reduced enzyme activity and fluconazole resistance through reduced affinity. J. Biol. Chem. 272, 5682-5688.
161. Loeffler, J., S. L. Kelly, H. Hebart, U. Schumaher, C. Lass Florl, and E. Einsele (1997). Molecular analysis of CYP51 from fluconazole-resistant Candida albicans strains. FEMS Lett. 151, 263-268.
162. Lamb, D. C, D. E. Kelly, T. C. White, and S. L. Kelly (2000). The R467K amino acid substitution in Candida albicans sterol 14a-demethylase causes drug resistance through reduced affinity. Antimicrob. Agents Chemother. 44, 63-67.
163. Favre, B., M. Didmon, and N. S. Ryder (1999). Multiple amino acid substitutions in lanosterol 14 alpha-demethylase contribute to azole resistance in Candida albicans. Microbiology 145, 2715-2725.
164. Marichal, P., L. Koymans, S. Willemsens, D. Bellens, P. Verhasselt, W. Luyten et al. (1999). Contribution of mutations to the cytochrome P450 14 alpha-demethylase (Erg11p, CYP51) to azole resistance in Candida albicans. Microbiology 145, 2701-2713.
165. Perea, S., J. L. Lopez-Ribot, W. R. Kirkpatrick, K. McAtee, R. A. Santillan, M. Martinez, D. Calabrese et al. (2001). Prevalence of molecular mechanisms of resistance to azole antifungal agents in Candida albicans strains displaying high-level fluconazole resistance isolated from human immunodeficiency virus infected patients. Antimicrob. Agents Chemother. 45, 2676-2684.
166. Boscott, P. E. and G. H. Grant (1994). Modeling cytochrome P450 14-alpha demethylase (Candida albicans) from P450CAM. J. Mol. Graph. 12, 185-192.
167. Ji, H. T., W. N. Zhang, Y. J. Zhou, Y. L. Song, J. Lu, and J. Zhu (2000). A three-dimensional model of lanosterol 14 alpha-demethylase of Candida albicans and its interaction with azole antifungals. J. Med. Chem. 43, 2495-2505.
168. Delye, C., F. Laigret, and M. F. Corio-Costet (1997). A mutation in the 14α-demethylase gene of Uncinula necator that correlates with resistance to a sterol biosynthesis inhibitor. Appl. Environ. Microbiol. 63, 2966-2970.
169. Cosme, X and E. F. Johnson (2000). Engineering microsomal cytochrome P450 2C5 to be a soluble, monomelic enzyme. J. Biol. Chem. 275, 2545-2553.
170. Williams, P. A., J. Cosme, V. Sridhar, E. F. Johnson and D. E. McCree (2000). Mammalian microsomal cytochrome P450 monooxygenase: Structural adaptations for membrane binding and functional diversity. Mol. Cell. 5, 121-131.
171. Joo, H., Z. L. Lin, and F. H. Arnold (1999). Laboratory evolution of peroxide-mediated cytochrome P450 hydroxylation. Nature 399, 670-673.