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Journal of Enzyme Inhibition Volume 14, 1999 - Issue 3
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Original Article

Molecular Modelling of Lanosterol 14α-Demethylase (CYPSl) from Saccharomyces Cerevisiae via Homology with CYP102, a Unique Bacterial Cytochrome P450 Isoform: Quantitative Structure-Activity Relationships (QSARs) within two Related Series of Antifungal Azole Derivatives

David F.V. Lewis School of Biological Sciences, University of Surrey, Guildford, Surrey, GU2 5XH, UKCorrespondence[email protected]
,
Alan Wiseman School of Biological Sciences, University of Surrey, Guildford, Surrey, GU2 5XH, UK
&
Mike H. Tarbit Glaxo Wellcome Research and Development Limited, Park Road, Ware, Hertfordshire, SG12 ODP, UK
Pages 175-192 | Received 20 Aug 1998, Published online: 02 Jul 2009

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David F. V. Lewis, Brian G. Lake & Maurice Dickins. (2007) Quantitative structure-activity relationships (QSARs) in inhibitors of various cytochromes P450: The importance of compound lipophilicity. Journal of Enzyme Inhibition and Medicinal Chemistry 22:1, pages 1-6.
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Chunquan Sheng, Wannian Zhang, Min Zhang, Yunlong Song, Haitao Ji, Jie Zhu, Jianzhong Yao, Jianxin Yu, Song Yang, Youjun Zhou, Jü Zhu & Jiaguo Lü. (2004) Homology Modeling of Lanosterol 14α-Demethylase of Candida albicans and Aspergillus fumigatus and Insights into the Enzyme-Substrate Interactions. Journal of Biomolecular Structure and Dynamics 22:1, pages 91-99.
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David F.V. Lewis & Maurice Dickins. (2001) Quantitative Structure-Activity Relationships (QSARs) Within Series of Inhibitors for Mammalian Cytochromes P450 (CYPs). Journal of Enzyme Inhibition 16:4, pages 321-330.
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Antonio Mastrolorenzo, Andrea Scozzafava & Claudiu T. Supuran. (2000) The Antifungal Activity of Sulfonylated/Carboxylated Derivatives of Dibenzo-1,4-Dioxine-2-Acetyloxime May Be Due to Inhibition of Lanosterol-14Al-Demethylase. Journal of Enzyme Inhibition 15:6, pages 557-569.
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Articles from other publishers (26)

Juan Cai & Rongwei Shi. (2023) Exploration of the binding of antifungal drugs to human P450 2C9 based on docking and molecular dynamics simulation . International Journal of Quantum Chemistry 123:14.
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Takahisa Watanabe, Tomohiro Ishikawa, Hirotaka Sato, Noriyuki Hirose, Lisa Nonaka, Kaori Matsumura, Akira Masubuchi, Kazuko Nishimura & Michiaki Masuda. (2021) Characterization of Prototheca CYP51/ERG11 as a possible target for therapeutic drugs . Medical Mycology 59:9, pages 855-863.
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Yong-Jin Wu & Nicholas A. Meanwell. (2021) Geminal Diheteroatomic Motifs: Some Applications of Acetals, Ketals, and Their Sulfur and Nitrogen Homologues in Medicinal Chemistry and Drug Design. Journal of Medicinal Chemistry 64:14, pages 9786-9874.
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Stephen Nesnow. 2016. Toxicogenomics in Predictive Carcinogenicity. Toxicogenomics in Predictive Carcinogenicity 280 351 .
Musang Liu, Nan Zheng, Dongmei Li, Hailin Zheng, Lili Zhang, Hu Ge & Weida Liu. (2016) cyp51A -based mechanism of azole resistance in Aspergillus fumigatus : Illustration by a new 3D Structural Model of Aspergillus fumigatus CYP51A protein . Medical Mycology 54:4, pages 400-408.
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Surajit Debnath & Soma Addya. (2014) Structural basis for heterogeneous phenotype of ERG11 dependent Azole resistance in C.albicans clinical isolates. SpringerPlus 3:1.
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Lalit Kumar, Nand Lal, Vikash Kumar, Amit Sarswat, Santosh Jangir, Veenu Bala, Lokesh Kumar, Bhavana Kushwaha, Atindra K. Pandey, Mohammad I. Siddiqi, Praveen K. Shukla, Jagdamba P. Maikhuri, Gopal Gupta & Vishnu L. Sharma. (2013) Azole–carbodithioate hybrids as vaginal anti-Candida contraceptive agents: Design, synthesis and docking studies. European Journal of Medicinal Chemistry 70, pages 68-77.
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Peter Hlavica. (2013) Evaluation of structural features in fungal cytochromes P450 predicted to rule catalytic diversification. Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics 1834:1, pages 205-220.
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Rayko Becher & Stefan G. R. Wirsel. (2012) Fungal cytochrome P450 sterol 14α-demethylase (CYP51) and azole resistance in plant and human pathogens. Applied Microbiology and Biotechnology 95:4, pages 825-840.
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P. Zoumpoulakis, Ch. Camoutsis, G. Pairas, M. Soković, J. Glamočlija, C. Potamitis & A. Pitsas. (2012) Synthesis of novel sulfonamide-1,2,4-triazoles, 1,3,4-thiadiazoles and 1,3,4-oxadiazoles, as potential antibacterial and antifungal agents. Biological evaluation and conformational analysis studies. Bioorganic & Medicinal Chemistry 20:4, pages 1569-1583.
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Yongwei Jiang, Yongbin Cao, Jun Zhang, Yan Zou, Xiaoyun Chai, Honggang Hu, Qingjie Zhao, Qiuye Wu, Dazhi Zhang, Yuanying Jiang & Qingyan Sun. (2011) Design, synthesis and antifungal evaluation of 1-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,4-triazol-5(4H)-one. European Journal of Medicinal Chemistry 46:7, pages 3135-3141.
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Jan Heeres, Lieven Meerpoel & Paul Lewi. (2010) Conazoles. Molecules 15:6, pages 4129-4188.
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Eveline Snelders, Anna Karawajczyk, Gijs Schaftenaar, Paul E. Verweij & Willem J. G. Melchers. (2010) Azole Resistance Profile of Amino Acid Changes in Aspergillus fumigatus CYP51A Based on Protein Homology Modeling . Antimicrobial Agents and Chemotherapy 54:6, pages 2425-2430.
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Qing-Yan Sun, Jian-Ming Xu, Yong-Bing Cao, Wan-Nian Zhang, Qiu-Ye Wu, Da-Zhi Zhang, Jun Zhang, Hui-Qing Zhao & Yuan-Ying Jiang. (2007) Synthesis of novel triazole derivatives as inhibitors of cytochrome P450 14α-demethylase (CYP51). European Journal of Medicinal Chemistry 42:9, pages 1226-1233.
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Sean Ekins, Dayna C. Mankowski, Dennis J. Hoover, Michael P. Lawton, Judith L. Treadway & H. James HarwoodJr.Jr.. (2007) Three-Dimensional Quantitative Structure-Activity Relationship Analysis of Human CYP51 Inhibitors. Drug Metabolism and Disposition 35:3, pages 493-500.
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Shuang-Hong Chen, Chun-Quan Sheng, Xiao-Hui Xu, Yuan-Ying Jiang, Wan-Nian Zhang & Cheng He. (2007) Identification of Y118 Amino Acid Residue in Candida albicans Sterol 14α-Demethylase Associated with the Enzyme Activity and Selective Antifungal Activity of Azole Analogues. Biological & Pharmaceutical Bulletin 30:7, pages 1246-1253.
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E. Ruge, H.C. Korting & C. Borelli. (2005) Current state of three-dimensional characterisation of antifungal targets and its use for molecular modelling in drug design. International Journal of Antimicrobial Agents 26:6, pages 427-441.
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Bernd Rupp, Stephan Raub, Christel Marian & Hans-Dieter Höltje. (2005) Molecular design of two sterol 14α-demethylase homology models and their interactions with the azole antifungals ketoconazole and bifonazole. Journal of Computer-Aided Molecular Design 19:3, pages 149-163.
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Marcel Amichot, Sophie Tarès, Alexandra Brun‐Barale, Laury Arthaud, Jean‐Marc Bride & Jean‐Baptiste Bergé. (2004) Point mutations associated with insecticide resistance in the Drosophila cytochrome P450 Cyp6a2 enable DDT metabolism . European Journal of Biochemistry 271:7, pages 1250-1257.
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Li Xiao, Vincent Madison, Andrew S. Chau, David Loebenberg, Robert E. Palermo & Paul M. McNicholas. (2004) Three-Dimensional Models of Wild-Type and Mutated Forms of Cytochrome P450 14α-Sterol Demethylases from Aspergillus fumigatus and Candida albicans Provide Insights into Posaconazole Binding . Antimicrobial Agents and Chemotherapy 48:2, pages 568-574.
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David F. V. Lewis. (2003) Quantitative structure–activity relationships (QSARs) within the cytochrome P450 system: QSARs describing substrate binding, inhibition and induction of P450s. InflammoPharmacology 11:1, pages 43-73.
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Marcel J. de Groot & Sean Ekins. (2002) Pharmacophore modeling of cytochromes P450. Advanced Drug Delivery Reviews 54:3, pages 367-383.
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Rajendra Prasad, Sneh Lata Panwar & Smriti. 2002. 155 201 .
Anton Laak, Nico Vermeulen & Marcel de Groot. 2001. Drug-Drug Interactions. Drug-Drug Interactions 505 548 .
David Lewis. 2001. Guide to Cytochromes P450. Guide to Cytochromes P450 164 210 .
Larissa M. Podust, Thomas L. Poulos & Michael R. Waterman. (2001) Crystal structure of cytochrome P450 14α-sterol demethylase (CYP51) from Mycobacterium tuberculosis in complex with azole inhibitors . Proceedings of the National Academy of Sciences 98:6, pages 3068-3073.
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