Aryl fluorosulfate analogues as potent antimicrobial agents: SAR, cytotoxicity and docking studies

Ravindar, L. and Bukhari, S. N. A. and Rakesh, K. P. and Manukumar, H. M. and Vivek, H. K. and Mallesha, N. and Xie, Zhi-Zhong and Qin, Hua-Li (2018) Aryl fluorosulfate analogues as potent antimicrobial agents: SAR, cytotoxicity and docking studies. Bioorganic Chemistry, 81. 107 - 118. ISSN 1090-2120

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A series of aryl fluorosulfate analogues (1–37) were synthesized and tested for in vitro antibacterial and antifungal studies, and validated by docking studies. The compounds 9, 12, 14, 19, 25, 26, 35, 36 and 37 exhibited superior antibacterial potency against tested bacterial strains, while compounds 2, 4, 5, 15, 35, 36 and 37 were found to have better antifungal activity against tested fungal strains, compared to standard antibiotic gentamicin and ketoconazole respectively. Among all the synthesized 37 analogs, compounds 25, 26, 35, 36 and 37 displayed excellent anti-biofilm property against Staphylococcus aureus. The structure–activity relationship (SAR) revealed that the antimicrobial activity depends upon the presence of –OSO2F group and slender effect of different substituent’s on the phenyl rings. The electron donating (OCH3) groups in analogs increase the antibacterial activity, and interestingly the electron withdrawing (Cl, NO2, F and Br) groups increase the antifungal activity (except compound 35, 36 and 37). The mechanism of potent compounds showed membrane damage on bacteria confirmed by SEM. Compounds 35, 36 and 37 exhibited highest glide g-scores in molecular docking studies and validated the biocidal property.

Item Type: Article
Uncontrolled Keywords: Aryl-fluorosulfates, Antimicrobial, Docking studies, Cytotoxicity
Subjects: B Life Science > Biotechnology
Divisions: Department of > Biotechnology
Depositing User: LA manjunath user
Date Deposited: 16 Oct 2019 09:54
Last Modified: 04 Jul 2020 05:21

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