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

Lekkala Ravindar, Bukhari Syed Nasir Abbas, K. P. Rakesh, H. M. Manukumar, H. K. Vivek, N. Mallesha, Zhi Zhong Xie, Hua Li Qin

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)107-118
Number of pages12
JournalBioorganic Chemistry
Volume81
DOIs
Publication statusPublished - 1 Dec 2018
Externally publishedYes

Fingerprint

Cytotoxicity
Anti-Infective Agents
Electrons
Ketoconazole
Biofilms
Gentamicins
Staphylococcus aureus
Bacteria
Anti-Bacterial Agents
Membranes
Scanning electron microscopy
In Vitro Techniques
3-(5-nitrofuryl)-7-(5-nitrofurfurylidene)-3,3a,4,5,6,7-hexahydro-2H-indazole

Keywords

  • Antimicrobial
  • Aryl-fluorosulfates
  • Cytotoxicity
  • Docking studies

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

Cite this

Ravindar, L., Syed Nasir Abbas, B., Rakesh, K. P., Manukumar, H. M., Vivek, H. K., Mallesha, N., ... Qin, H. L. (2018). Aryl fluorosulfate analogues as potent antimicrobial agents: SAR, cytotoxicity and docking studies. Bioorganic Chemistry, 81, 107-118. https://doi.org/10.1016/j.bioorg.2018.08.001

Aryl fluorosulfate analogues as potent antimicrobial agents : SAR, cytotoxicity and docking studies. / Ravindar, Lekkala; Syed Nasir Abbas, Bukhari; Rakesh, K. P.; Manukumar, H. M.; Vivek, H. K.; Mallesha, N.; Xie, Zhi Zhong; Qin, Hua Li.

In: Bioorganic Chemistry, Vol. 81, 01.12.2018, p. 107-118.

Research output: Contribution to journalArticle

Ravindar, L, Syed Nasir Abbas, B, Rakesh, KP, Manukumar, HM, Vivek, HK, Mallesha, N, Xie, ZZ & Qin, HL 2018, 'Aryl fluorosulfate analogues as potent antimicrobial agents: SAR, cytotoxicity and docking studies', Bioorganic Chemistry, vol. 81, pp. 107-118. https://doi.org/10.1016/j.bioorg.2018.08.001
Ravindar L, Syed Nasir Abbas B, Rakesh KP, Manukumar HM, Vivek HK, Mallesha N et al. Aryl fluorosulfate analogues as potent antimicrobial agents: SAR, cytotoxicity and docking studies. Bioorganic Chemistry. 2018 Dec 1;81:107-118. https://doi.org/10.1016/j.bioorg.2018.08.001
Ravindar, Lekkala ; Syed Nasir Abbas, Bukhari ; Rakesh, K. P. ; Manukumar, H. M. ; Vivek, H. K. ; Mallesha, N. ; Xie, Zhi Zhong ; Qin, Hua Li. / Aryl fluorosulfate analogues as potent antimicrobial agents : SAR, cytotoxicity and docking studies. In: Bioorganic Chemistry. 2018 ; Vol. 81. pp. 107-118.
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