Comparison of lanosterol-14α-demethylase (CYP51) of human and Candida albicans for inhibition by different antifungal azoles

Buters, 1994, cDNA-directed expression of human cytochrome P450 CYP3A4 using baculovirus, Drug Metab. Dispos., 22, 688 Byskov, 2002, Role of meiosis activating sterols, MAS, in induced oocyte maturation, Mol. Cell. Endocrinol., 187, 189, 10.1016/S0303-7207(01)00707-9 Chen, 1997, Coexpression of cytochrome P4502A6 and human NADPH-P450 oxidoreductase in the baculovirus system, Drug Metab. Dispos., 25, 399 Crespi, 1999, The use of heterologously expressed drug metabolizing enzymes—state of the art and prospects for the future, Pharmacol. Ther., 84, 121, 10.1016/S0163-7258(99)00028-5 Gonzalez, 1991, Expression of mammalian cytochrome P450 using baculovirus, Meth. Enzymol., 206, 93, 10.1016/0076-6879(91)06080-M Kakkar, 1999, Estimation of Ki in a competitive enzyme-inhibition model: comparisons among three methods of data analysis, Drug Metab. Dispos., 27, 756 Lamb, 2000, Differential inhibition of human CYP3A4 and Candida albicans CYP51 with azole antifungal agents, Chem. Biol. Interact., 125, 165, 10.1016/S0009-2797(99)00169-6 Lamb, 1999, Biodiversity of the P450 catalytic cycle: yeast cytochrome b5/NADH cytochrome b5 reductase complex efficiently drives the entire sterol 14-demethylation (CYP51) reaction, FEBS Lett., 462, 283, 10.1016/S0014-5793(99)01548-3 Lamb, 1997, Reduced intracellular accumulation of azole antifungal results in resistance in Candida albicans isolate NCPF 3363, FEMS Microbiol. Lett., 147, 189, 10.1111/j.1574-6968.1997.tb10240.x Lamb, 1997, The mutation T315A in Candida albicans sterol 14alpha-demethylase causes reduced enzyme activity and fluconazole resistance through reduced affinity, J. Biol. Chem., 272, 5682, 10.1074/jbc.272.9.5682 Lamb, 1999, Characteristics of the heterologously expressed human lanosterol 14alpha-demethylase (other names: P45014DM, CYP51, P45051) and inhibition of the purified human and Candida albicans CYP51 with azole antifungal agents, Yeast, 15, 755, 10.1002/(SICI)1097-0061(19990630)15:9<755::AID-YEA417>3.0.CO;2-8 Lee, 1995, CYP3A4 expressed by insect cells infected with a recombinant baculovirus containing both CYP3A4 and human NADPH-cytochrome P450 reductase is catalytically similar to human liver microsomal CYP3A4, Arch. Biochem. Biophys., 319, 157, 10.1006/abbi.1995.1278 Lepesheva, 2001, Folding requirements are different between sterol 14alpha-demethylase (CYP51) from Mycobacterium tuberculosis and human or fungal orthologs, J. Biol. Chem., 276, 28413, 10.1074/jbc.M102767200 Lepesheva, 2004, CYP51—the omnipotent P450, Mol. Cell. Endocrinol., 215, 165, 10.1016/j.mce.2003.11.016 Nelson, D.R., 2006. http://www.drnelson.utmem.edu/CytochromeP450.html. Omura, 1964, The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature, J. Biol. Chem., 239, 2370, 10.1016/S0021-9258(20)82244-3 Rozman, 1998, Lanosterol 14alpha-demethylase (CYP51) and spermatogenesis, Drug Metab. Dispos., 26, 1199 Sutter, 1990, Isolation and characterization of the alkane-inducible NADPH-cytochrome P-450 oxidoreductase gene from Candida tropicalis. Identification of invariant residues within similar amino acid sequences of divergent flavoproteins, J. Biol. Chem., 265, 16428, 10.1016/S0021-9258(17)46240-5 Trosken, 2005, Quantitation of 13 azole fungicides in wine samples by liquid chromatography–tandem mass spectrometry, J. Chromatogr. A, 1083, 113, 10.1016/j.chroma.2005.06.020 Trosken, 2004, Comparative assessment of the inhibition of human recombinant CYP19 (aromatase) by azoles used in agriculture and as drugs for humans, Endocr. Res., 30, 387, 10.1081/ERC-200035093 Trosken, 2004, Quantitation of lanosterol and its major metabolite FF-MAS in an inhibition assay of CYP51 by azoles with atmospheric pressure photoionization based LC–MS/MS, J. Am. Soc. Mass Spectrom., 15, 1216, 10.1016/j.jasms.2004.04.036 Trzaskos, 1989, Comparative effects of the azole-based fungicide flusilazole on yeast and mammalian lanosterol 14 alpha-methyl demethylase, Antimicrob. Agents Chemother., 33, 1228, 10.1128/AAC.33.8.1228 Vanden Bossche, 1987, Interaction of azole derivatives with cytochrome P-450 isozymes in yeast, fungi, plants and mammalian cells, Pestic. Sci., 21, 289, 10.1002/ps.2780210406 Vanden Bossche, 1998, Cytochromes P450 in fungi, Mycoses, 41, 32, 10.1111/j.1439-0507.1998.tb00581.x Zarn, 2003, Azole fungicides affect mammalian steroidogenesis by inhibiting sterol 14 alpha-demethylase and aromatase, Environ. Health Perspect., 111, 255, 10.1289/ehp.5785