Cited by 459Antifungal resistance and susceptibilityFungal Plant Pathogen ControlMicrobial Natural Products and Biosynthesis

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Structural analyses of Candida albicans sterol 14α-demethylase complexed with azole drugs address the molecular basis of azole-mediated inhibition of fungal sterol biosynthesis

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Hargrove, Tatiana Y., Friggeri, Laura, Wawrzak, Zdzislaw, Qi, Aidong, Hoekstra, William J., Schotzinger, Robert J., York, John D., Guengerich, F. Peter, Lepesheva, Galina I.·2017·Journal of Biological Chemistry

DOI 10.1074/jbc.m117.778308PMC PMC5399120

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Abstract

With some advances in modern medicine (such as cancer chemotherapy, broad exposure to antibiotics, and immunosuppression), the incidence of opportunistic fungal pathogens such as Candida albicans has increased. Cases of drug resistance among these pathogens have become more frequent, requiring the development of new drugs and a better understanding of the targeted enzymes. Sterol 14α-demethylase (CYP51) is a cytochrome P450 enzyme required for biosynthesis of sterols in eukaryotic cells and is the major target of clinical drugs for managing fungal pathogens, but some of the CYP51 key features important for rational drug design have remained obscure. We report the catalytic properties, ligand-binding profiles, and inhibition of enzymatic activity of C. albicans CYP51 by clinical antifungal drugs that are used systemically (fluconazole, voriconazole, ketoconazole, itraconazole, and posaconazole) and topically (miconazole and clotrimazole) and by a tetrazole-based drug candidate, VT-1161 (oteseconazole: ( R )-2-(2,4-difluorophenyl)-1,1-difluoro-3-(1 H -tetrazol-1-yl)-1-(5-(4-(2,2,2-trifluoroethoxy)phenyl)pyridin-2-yl)propan-2-ol). Among the compounds tested, the first-line drug fluconazole was the weakest inhibitor, whereas posaconazole and VT-1161 were the strongest CYP51 inhibitors. We determined the X-ray structures of C. albicans CYP51 complexes with posaconazole and VT-1161, providing a molecular mechanism for the potencies of these drugs, including the activity of VT-1161 against Candida krusei and Candida glabrata , pathogens that are intrinsically resistant to fluconazole. Our comparative structural analysis outlines phylum-specific CYP51 features that could direct future rational development of more efficient broad-spectrum antifungals.

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Authors: Hargrove, T. Y., Friggeri, L., Wawrzak, Z., Qi, A., Hoekstra, W. J., Schotzinger, R. J., York, J. D., Guengerich, F. P., & Lepesheva, G. I.
Affiliations: Vanderbilt University (US)
Northwestern University (US)
Viamet Pharmaceuticals (United States) (US)
Corresponding author: Lepesheva, Galina I.
ORCID: Wawrzak, Zdzislaw
York, John D.
Guengerich, F. Peter
Lepesheva, Galina I.
Venue: Journal of Biological Chemistry
Publisher: Elsevier BV
Published: 2017-04
Volume: 292
Issue: 16
Pages: 6728-6743
ISSN: 0021-9258 (ISSN-L)
DOI: 10.1074/jbc.m117.778308
PMC: PMC5399120
OpenAlex: W2593598577
Cited by: 444
References: 57
Citations by year: 2026: 67 · 2025: 82 · 2024: 49 · 2023: 64 · 2022: 55 · 2021: 30 · 2020: 39 · 2019: 25 · 2018: 24 · 2017: 9
FWCI: 21.04
Type: journal article
Language: en
Open access: hybrid
doi.org
Licence: cc-by
www.elsevier.com/tdm/userlicense/1.0/ (tdm)
creativecommons.org/licenses/by/4.0/ (vor, 1243 d)
Locations: Journal of Biological Chemistry (publishedVersion, cc-by)
Europe PMC (PubMed Central) (publishedVersion)
PubMed Central (publishedVersion)
PubMed (publishedVersion)
Funders: National Institutes of Health (R01 GM067871)
Topics: Health Sciences › Medicine › Infectious Diseases › Antifungal resistance and susceptibility
Life Sciences › Agricultural and Biological Sciences › Plant Science › Fungal Plant Pathogen Control
Life Sciences › Immunology and Microbiology › Applied Microbiology and Biotechnology › Microbial Natural Products and Biosynthesis
Keywords: Candida albicans, sterol 14α-demethylase, CYP51, cytochrome P450, azole antifungals, posaconazole, oteseconazole, fluconazole, ketoconazole, voriconazole, itraconazole, miconazole, clotrimazole, fungal sterol biosynthesis, drug resistance, Candida krusei, Candida glabrata, X-ray crystal structure, ligand binding, antifungal drug design
MeSH terms: Animals, Antifungal Agents, Azoles, Candida albicans, Crystallization, Fungal Proteins, Heme, Humans, Kinetics, Ligands, Microbial Sensitivity Tests, Protein Binding, Protein Conformation, Protons, Sterols, Rats, Sterol 14-Demethylase

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Structural analyses of Candida albicans sterol 14α-demethylase complexed with azole drugs address the molecular basis of azole-mediated inhibition of fungal sterol biosynthesis

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