Design, synthesis and antimicrobial evaluation of novel glycosylated-fluoroquinolones derivatives

Herein we report the design, synthesis and biological evaluation of structurally modified ciprofloxacin, norfloxacin and moxifloxacin standard drugs, featuring amide functional groups at C-3 of the fluoroquinolone scaffold. In vitro antimicrobial testing against various Gram-positive bacteria, Gram-...

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Bibliographic Details
Published inEuropean journal of medicinal chemistry Vol. 202; pp. 112513 - 112522
Main Authors Mohammed, Aya A.M., Suaifan, Ghadeer A.R.Y., Shehadeh, Mayadah B., Okechukwu, Patrick N.
Format Journal Article
LanguageEnglish
Published ISSY-LES-MOULINEAUX Elsevier Masson SAS 15.09.2020
Elsevier
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Summary:Herein we report the design, synthesis and biological evaluation of structurally modified ciprofloxacin, norfloxacin and moxifloxacin standard drugs, featuring amide functional groups at C-3 of the fluoroquinolone scaffold. In vitro antimicrobial testing against various Gram-positive bacteria, Gram-negative bacteria and fungi revealed potential antibacterial and antifungal activity. Hybrid compounds 9 (MIC 0.2668 ± 0.0001 mM), 10 (MIC 0.1358 ± 00025 mM) and 13 (MIC 0.0898 ± 0.0014 mM) had potential antimicrobial activity against a fluoroquinolone-resistant Escherichia coli clinical isolate, compared to ciprofloxacin (MIC 0.5098 ± 0.0024 mM) and norfloxacin (MIC 0.2937 ± 0.0021 mM) standard drugs. Interestingly, compound 10 also exerted potential antifungal activity against Candida albicans (MIC 0.0056 ± 0.0014 mM) and Penicillium chrysogenum (MIC 0.0453 ± 0.0156 mM). Novel derivatives and standard fluoroquinolone drugs exhibited near-identical cytotoxicity levels against L6 muscle cell-line, when measured using the MTT assay. [Display omitted] •Glucosamine-fluoroquinolone conjugation was made possible through a simple synthetic pathway.•Fluoroquinolone hybrids potentially inhibited clinical fluoroquinolones resistant Escherichia coli isolate.•Compound 10 exerted potential antifungal activity against Candida albicans and P. chrysogenum.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2020.112513