Synthesis and antimicrobial evaluation of new nitric oxide-donating fluoroquinolone/oxime hybrids

Hossameldin A. Aziz, Gamal A.I. Moustafa, Gamal El Din A. Abuo-Rahma, Safwat M. Rabea, Glenn Hauk, Vagolu S. Krishna, Dharmarajan Sriram, James M. Berger, Samar H. Abbas

Research output: Contribution to journalArticlepeer-review

Abstract

A new series of nitric oxide-donating fluoroquinolone/oximes was prepared in this study. The nitric oxide release from the prepared compounds was measured using a modified Griess colorimetric method. The antitubercular evaluation of the synthesized compounds indicated that ketone derivatives 2b and 2e and oximes 3b and 3d exhibited somewhat higher activity than their respective parent fluoroquinolones. Mycobacterial DNA cleavage studies and molecular modeling of Mycobacterium tuberculosis DNA gyrase were pursued to explain the observed bioactivity. More important, antibacterial evaluation showed that oximes 3c–e are highly potent against Klebsiella pneumoniae, with minimum inhibitory concentration (MIC) values of 0.06, 0.08, and 0.034 µM, respectively, whereas ketone 2c and oxime 4c are more active against Staphylococcus aureus than ciprofloxacin (MIC values: 0.7, 0.38, and 1.6 µM, respectively). Notably, the antipseudomonal activities of compounds 2a and 4c were much higher than those of their respective parent fluoroquinolones.

Original languageEnglish (US)
Article number2000180
JournalArchiv der Pharmazie
Volume354
Issue number1
DOIs
StatePublished - Jan 2021

Keywords

  • antibacterial
  • antitubercular
  • cleavable DNA complex
  • fluoroquinolones
  • nitric oxide

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery

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