Benzoic acid derivatives with improved antifungal activity: Design, synthesis, structure–activity relationship (SAR) and CYP53 docking studies
作者： Sabina Berne , Lidija Kovačič , Matej Sova , Nada Kraševec , Stanislav Gobec
DOI: 10.1016/J.BMC.2015.06.042
关键词:
摘要: Previously, we identified CYP53 as a fungal-specific target of natural phenolic antifungal compounds and discovered several inhibitors with properties. In this study, performed similarity-based virtual screening synthesis to obtain benzoic acid-derived assessed their activity against Cochliobolus lunatus, Aspergillus niger Pleurotus ostreatus. addition, generated structural models enzyme used them in docking trials 40 selected compounds. Finally, explored CYP53-ligand interactions elements conferring increased facilitate the development potential new agents that specifically enzymes animal plant pathogenic fungi.
sci-hub.se 参考文章(45)
Caroline S. Harwood, Rebecca E. Parales, THE β-KETOADIPATE PATHWAY AND THE BIOLOGY OF SELF-IDENTITY Annual Review of Microbiology. ,vol. 50, pp. 553- 590 ,(1996) , 10.1146/ANNUREV.MICRO.50.1.553
Steven L. Kelly, Diane E. Kelly, Microbial cytochromes P450: biodiversity and biotechnology. Where do cytochromes P450 come from, what do they do and what can they do for us? Philosophical Transactions of the Royal Society B. ,vol. 368, pp. 20120476- 20120476 ,(2013) , 10.1098/RSTB.2012.0476
Venkatesh Moktali, Jongsun Park, Natalie D Fedorova-Abrams, Bongsoo Park, Jaeyoung Choi, Yong-Hwan Lee, Seogchan Kang, Systematic and Searchable Classification of Cytochrome P450 Proteins Encoded by Fungal and Oomycete Genomes BMC Genomics. ,vol. 13, pp. 525- 525 ,(2012) , 10.1186/1471-2164-13-525
Reut Hazan, Alexandra Levine, Hagai Abeliovich, Benzoic acid, a weak organic acid food preservative, exerts specific effects on intracellular membrane trafficking pathways in Saccharomyces cerevisiae. Applied and Environmental Microbiology. ,vol. 70, pp. 4449- 4457 ,(2004) , 10.1128/AEM.70.8.4449-4457.2004
H. Fukuda, K. Nakamura, E. Sukita, T. Ogawa, T. Fujii, Cytochrome P450rm from Rhodotorula minuta Catalyzes 4-Hydroxylation of Benzoate Journal of Biochemistry. ,vol. 119, pp. 314- 318 ,(1996) , 10.1093/OXFORDJOURNALS.JBCHEM.A021241
Aalt D. J. van Dijk, Alexandre M. J. J. Bonvin, Solvated docking: introducing water into the modelling of biomolecular complexes Bioinformatics. ,vol. 22, pp. 2340- 2347 ,(2006) , 10.1093/BIOINFORMATICS/BTL395
Matthew C. Fisher, Daniel. A. Henk, Cheryl J. Briggs, John S. Brownstein, Lawrence C. Madoff, Sarah L. McCraw, Sarah J. Gurr, Emerging fungal threats to animal, plant and ecosystem health Nature. ,vol. 484, pp. 186- 194 ,(2012) , 10.1038/NATURE10947
Łukasz Gricman, Constantin Vogel, Jürgen Pleiss, Conservation analysis of class-specific positions in cytochrome P450 monooxygenases: functional and structural relevance. Proteins. ,vol. 82, pp. 491- 504 ,(2014) , 10.1002/PROT.24415
Brian C. Monk, Thomas M. Tomasiak, Mikhail V. Keniya, Franziska U. Huschmann, Joel D. A. Tyndall, Joseph D. O’Connell, Richard D. Cannon, Jeffrey G. McDonald, Andrew Rodriguez, Janet S. Finer-Moore, Robert M. Stroud, Architecture of a single membrane spanning cytochrome P450 suggests constraints that orient the catalytic domain relative to a bilayer. Proceedings of the National Academy of Sciences of the United States of America. ,vol. 111, pp. 3865- 3870 ,(2014) , 10.1073/PNAS.1324245111
Dan Fishelovitch, Sason Shaik, Haim J. Wolfson, Ruth Nussinov, Theoretical Characterization of Substrate Access/Exit Channels in the Human Cytochrome P450 3A4 Enzyme: Involvement of Phenylalanine Residues in the Gating Mechanism Journal of Physical Chemistry B. ,vol. 113, pp. 13018- 13025 ,(2009) , 10.1021/JP810386Z