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Azole fungicides affect mammalian steroidogenesis by inhibiting sterol 14 alpha-demethylase and aromatase.

Zarn JA, Brüschweiler BJ, Schlatter JR.

Environ Health Perspect. 2003 Mar;111(3):255-61. Review.PMID: 12611652 [PubMed - indexed for MEDLINE]Related articlesFree article

Comparative assessment of the inhibition of recombinant human CYP19 (aromatase) by azoles used in agriculture and as drugs for humans.

Trösken ER, Scholz K, Lutz RW, Völkel W, Zarn JA, Lutz WK.

Endocr Res. 2004 Aug;30(3):387-94.PMID: 15554355 [PubMed - indexed for MEDLINE]Related articles

Cloning and expression in Escherichia coli of the obtusifoliol 14 alpha-demethylase of Sorghum bicolor (L.) Moench, a cytochrome P450 orthologous to the sterol 14 alpha-demethylases (CYP51) from fungi and mammals.

Bak S, Kahn RA, Olsen CE, Halkier BA.

Plant J. 1997 Feb;11(2):191-201.PMID: 9076987 [PubMed - indexed for MEDLINE]Related articles

Plant sterol 14 alpha-demethylase affinity for azole fungicides.

Lamb DC, Cannieux M, Warrilow AG, Bak S, Kahn RA, Manning NJ, Kelly DE, Kelly SL.

Biochem Biophys Res Commun. 2001 Jun 15;284(3):845-9.PMID: 11396979 [PubMed - indexed for MEDLINE]Related articles

Mode of action and resistance to azole antifungals associated with the formation of 14 alpha-methylergosta-8,24(28)-dien-3 beta,6 alpha-diol.

Kelly SL, Lamb DC, Corran AJ, Baldwin BC, Kelly DE.

Biochem Biophys Res Commun. 1995 Feb 27;207(3):910-5.PMID: 7864896 [PubMed - indexed for MEDLINE]Related articles

Inhibition of human CYP19 by azoles used as antifungal agents and aromatase inhibitors, using a new LC-MS/MS method for the analysis of estradiol product formation.

Trösken ER, Fischer K, Völkel W, Lutz WK.

Toxicology. 2006 Feb 15;219(1-3):33-40. Epub 2005 Dec 5.PMID: 16330141 [PubMed - indexed for MEDLINE]Related articles

Azole antifungals are potent inhibitors of cytochrome P450 mono-oxygenases and bacterial growth in mycobacteria and streptomycetes.

McLean KJ, Marshall KR, Richmond A, Hunter IS, Fowler K, Kieser T, Gurcha SS, Besra GS, Munro AW.

Microbiology. 2002 Oct;148(Pt 10):2937-49.PMID: 12368427 [PubMed - indexed for MEDLINE]Related articlesFree article

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

Trösken ER, Adamska M, Arand M, Zarn JA, Patten C, Völkel W, Lutz WK.

Toxicology. 2006 Nov 10;228(1):24-32. Epub 2006 Aug 12.PMID: 16989930 [PubMed - indexed for MEDLINE]Related articles

Expression and homology modelling of sterol 14alpha-demethylase of Magnaporthe grisea and its interaction with azoles.

Yang J, Zhang Q, Liao M, Xiao M, Xiao W, Yang S, Wan J.

Pest Manag Sci. 2009 Mar;65(3):260-5.PMID: 19152375 [PubMed - indexed for MEDLINE]Related articles

Altered P450 activity associated with direct selection for fungal azole resistance.

Joseph-Horne T, Hollomon D, Loeffler RS, Kelly SL.

FEBS Lett. 1995 Oct 30;374(2):174-8.PMID: 7589528 [PubMed - indexed for MEDLINE]Related articles

Cytochrome P450 of fungi: primary target for azole antifungal agents.

Yoshida Y.

Curr Top Med Mycol. 1988;2:388-418. Review.PMID: 3288361 [PubMed - indexed for MEDLINE]Related articles

Effects of Y132H and F145L substitutions on the activity, azole resistance and spectral properties of Candida albicans sterol 14-demethylase P450 (CYP51): a live example showing the selection of altered P450 through interaction with environmental compounds.

Kudo M, Ohi M, Aoyama Y, Nitahara Y, Chung SK, Yoshida Y.

J Biochem. 2005 May;137(5):625-32.PMID: 15944416 [PubMed - indexed for MEDLINE]Related articles

Interaction of azole antifungal antibiotics with cytochrome P-450-dependent 14 alpha-sterol demethylase purified from Candida albicans.

Hitchcock CA, Dickinson K, Brown SB, Evans EG, Adams DJ.

Biochem J. 1990 Mar 1;266(2):475-80.PMID: 2180400 [PubMed - indexed for MEDLINE]Related articlesFree article

Sterol 14 alpha-demethylase and its inhibition: structural considerations on interaction of azole antifungal agents with lanosterol 14 alpha-demethylase (P-450(14DM)) of yeast.

Yoshida Y, Aoyama Y.

Biochem Soc Trans. 1991 Aug;19(3):778-82. Review. No abstract available. PMID: 1783215 [PubMed - indexed for MEDLINE]Related articles

Structural requirements for substrate recognition of Mycobacterium tuberculosis 14 alpha-demethylase: implications for sterol biosynthesis.

Bellamine A, Mangla AT, Dennis AL, Nes WD, Waterman MR.

J Lipid Res. 2001 Jan;42(1):128-36.PMID: 11160374 [PubMed - indexed for MEDLINE]Related articlesFree article

Inhibition of 14 alpha-sterol demethylase activity in Candida albicans Darlington does not correlate with resistance to azole.

Hitchcock CA, Barrett-Bee KJ, Russell NJ.

J Med Vet Mycol. 1987 Oct;25(5):329-33.PMID: 3323450 [PubMed - indexed for MEDLINE]Related articles

Structural diversities of active site in clinical azole-bound forms between sterol 14alpha-demethylases (CYP51s) from human and Mycobacterium tuberculosis.

Matsuura K, Yoshioka S, Tosha T, Hori H, Ishimori K, Kitagawa T, Morishima I, Kagawa N, Waterman MR.

J Biol Chem. 2005 Mar 11;280(10):9088-96. Epub 2004 Dec 20.PMID: 15611056 [PubMed - indexed for MEDLINE]Related articlesFree article

Cytochrome P-450-dependent 14 alpha-sterol demethylase of Candida albicans and its interaction with azole antifungals.

Hitchcock CA.

Biochem Soc Trans. 1991 Aug;19(3):782-7. Review. No abstract available. PMID: 1783216 [PubMed - indexed for MEDLINE]Related articles

Aromatase inhibitors: past, present and future.

Séralini G, Moslemi S.

Mol Cell Endocrinol. 2001 Jun 10;178(1-2):117-31. Review.PMID: 11403901 [PubMed - indexed for MEDLINE]Related articles

[Azole resistance in Candida spp]

Kakeya H, Miyazaki T, Miyazaki Y, Kohno S.

Nippon Ishinkin Gakkai Zasshi. 2003;44(2):87-92. Review. Japanese. PMID: 12748589 [PubMed - indexed for MEDLINE]Related articlesFree article