Prothioconazole and prothioconazole-desthio activities against Candida albicans sterol 14-α-Demethylase

Applied and Environmental Microbiology

Volumn 79, Issue 5, 2013, Pages 1639-1645

  Parker, Josie E ^a   Warrilow, Andrew G S ^a   Cools, Hans J ^b   Fraaije, Bart A ^b   Lucas, John A ^b   Rigdova, Katarina ^a   Griffiths, William J ^a   Kelly, Diane E ^a   Kelly, Steven L ^a  

^a SWANSEA UNIVERSITY   (United Kingdom)

^b ROTHAMSTED RESEARCH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALBICANS; ANTIFUNGAL ACTIONS; AZOLE ANTIFUNGALS; BINDING PROPERTIES; CANDIDA ALBICANS; CELL-FREE ASSAYS; DEMETHYLASE; IN-VITRO; LANOSTEROL; TYPE II; VORICONAZOLE;

ALCOHOLS; BINDING ENERGY; PORPHYRINS; YEAST;

CANDIDA;

ANTIFUNGAL AGENT; ENZYME INHIBITOR; PROTHIOCONAZOLE; PYRIMIDINE DERIVATIVE; STEROL 14ALPHA DEMETHYLASE; TRIAZOLE DERIVATIVE; VORICONAZOLE;

AGRICULTURAL APPLICATION; BIOASSAY; COMPARATIVE STUDY; ENZYME ACTIVITY; FUNGICIDE; FUNGUS; GROWTH RATE; SUBSTRATE;

ARTICLE; CANDIDA ALBICANS; DRUG EFFECT; ENZYMOLOGY; METABOLISM; PROTEIN BINDING;

ANTIFUNGAL AGENTS; CANDIDA ALBICANS; ENZYME INHIBITORS; PROTEIN BINDING; PYRIMIDINES; STEROL 14-DEMETHYLASE; TRIAZOLES;

EID: 84874732792     PISSN: 00992240     EISSN: 10985336     Source Type: Journal    
DOI: 10.1128/AEM.03246-12     Document Type: Article

References (20)

1. Kelly SL, Lamb DC, Jackson CJ, Warrilow AG, Kelly DE. 2003. The biodiversity of microbial cytochromes P450. Adv. Microb. Physiol. 47: 131-186.
2. Jefcoate CR, Gaylor JL, Calabrese RL. 1969. Ligand interactions with cytochrome P450. I. Binding of primary amines. Biochemistry 8:3455- 3463.
3. Lepesheva GI, Park HW, Hargrove TY, Vanhollebeke B, Wawrzak Z, Harp JM, Sundaramoorthy M, Nes WD, Pays E, Chaudhuri M, Villalta F, Waterman MR. 2010. Crystal structures of Trypanosoma brucei sterol 14α-demethylase and implications for selective treatment of human infections. J. Biol. Chem. 285:1773-1780.
4. Strushkevich N, Usanov SA, Park HW. 2010. Structural basis of human CYP51 inhibition by antifungal azoles. J. Mol. Biol. 397:1067-1078.
5. Parker JE, Warrilow AG, Cools HJ, Martel CM, Nes WD, Fraaije BA, Lucas JA, Kelly DE, Kelly SL. 2011. Mechanism of binding of prothioconazole to Mycosphaerella graminicola CYP51 differs from that of other azole antifungals. Appl. Environ. Microbiol. 77:1460 -1465.
6. Cools HJ, Fraaije BA. 26 April 2012. Update on mechanisms of azole resistance in Mycosphaerella graminicola and implications for future control. Pest Manag. Sci. [Epub ahead of print.] doi:10.1002/ps.3348.
7. Australian Pesticides and Veterinary Medicines Authority. 2007. Evaluation of the new active prothioconazole in the product redigo fungicidal seed treatment. ISSN 1443-1335. Australian Pesticides and Veterinary Medicines Authority, Symonston, Australian Capital Territory, Australia.
8. United States Environmental Protection Agency. 2007. Pesticide fact sheet: prothioconazole (7501 P). Office of Prevention, Pesticides and Toxic Substances, United States Environmental Protection Agency, Washington, DC.
9. Warrilow AG, Martel CM, Parker JE, Melo N, Lamb DC, Nes WD, Kelly DE, Kelly SL. 2010. Azole binding properties of Candida albicans sterol 14-alpha demethylase (CaCYP51). Antimicrob. Agents Chemother. 54:4235- 4245.
10. Johnson LB, Kauffman CA. 2003. Voriconazole: a new triazole antifungal agent. Clin. Infect. Dis. 36:630-637.
11. Lutz JD, Dixit V, Yeung CK, Dickmann LJ, Zelter A, Thatcher JE, Nelson WL, Isoherranen N. 2009. Expression and functional characterization of cytochrome P450 26A1, a retinoic acid hydroxylase. Biochem. Pharmacol. 77:258 -268.
12. Morrison JF. 1969. Kinetics of the reversible inhibition of enzymecatalysed reactions by tight-binding inhibitors. Biochim. Biophys. Acta 185:269 -286.
13. Copeland RA. 2005. Evaluation of enzyme inhibitors in drug discovery: a guide for medicinal chemists an pharmacologists, p 178 -213. Wiley-Interscience, New York, NY.
14. Warrilow AG, Jackson CJ, Parker JE, Marczylo TH, Kelly DE, Lamb DC, Kelly SL. 2009. Identification, characterization, and azole-binding properties of Mycobacterium smegmatis CYP164A2, a homolog of ML2088, the sole cytochrome P450 gene of Mycobacterium leprae. Antimicrob. Agents Chemother. 53:1157-1164.
15. Venkateswarlu K, Lamb DC, Kelly DE, Manning NJ, Kelly SL. 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.
16. Kelly SL, Lamb DC, Corran AJ, Baldwin BC, Kelly DE. 1995. Mode of action and resistance to azole antifungals associated with the formation of 14 alpha-methylergosta-8,24(28)-dien-3 β,6α-diol. Biochem. Biophys. Res. Commun. 207:910 -915.
17. Jefcoate CR. 1978. Measurement of substrate and inhibitor binding to microsomal cytochrome P-450 by optical-difference spectroscopy. Methods Enzymol. 52:258 -279.
18. Food and Agriculture Organization (FAO) of the United Nations/ World Health Organization (WHO). 2008. Pesticide residues in food 2008: joint FAO/WHO meeting on pesticide residues, New York, NY, p 265-292. FAO plant production and protection paper 193. ISSN 0259-2517. Food and Agriculture Organization of the United Nations, Rome, Italy.
19. Podust LM, Stojan J, Poulos TL, Waterman MR. 2001. Substrate recognition sites in 14α-sterol demethylase from comparative analysis of amino acid sequences and X-ray structure of Mycobacterium tuberculosis CYP51. J. Inorg. Biochem. 87:227-235.
20. Lamb DC, Kelly DE, Schunck WH, Shyadehi AZ, Akhtar M, Lowe DJ, Baldwin BC, Kelly SL. 1997. The mutation T315A in Candida albicans sterol 14α-demethylase causes reduced enzyme activity and fluconazole resistance through reduced affinity. J. Biol. Chem. 272:5682-5688.