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Synthesis and antimicrobial evaluation of new nitric oxide-donating fluoroquinolone/oxime hybrids.
- Source :
-
Archiv der Pharmazie [Arch Pharm (Weinheim)] 2021 Jan; Vol. 354 (1), pp. e2000180. Date of Electronic Publication: 2020 Sep 21. - Publication Year :
- 2021
-
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.<br /> (© 2020 Deutsche Pharmazeutische Gesellschaft.)
- Subjects :
- Anti-Bacterial Agents chemical synthesis
Anti-Bacterial Agents chemistry
Antitubercular Agents chemical synthesis
Antitubercular Agents chemistry
Antitubercular Agents pharmacology
Bacteria drug effects
Ciprofloxacin pharmacology
Fluoroquinolones chemical synthesis
Fluoroquinolones chemistry
Microbial Sensitivity Tests
Models, Molecular
Nitric Oxide metabolism
Nitric Oxide Donors chemical synthesis
Nitric Oxide Donors chemistry
Oximes chemical synthesis
Oximes chemistry
Structure-Activity Relationship
Anti-Bacterial Agents pharmacology
Fluoroquinolones pharmacology
Nitric Oxide Donors pharmacology
Oximes pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1521-4184
- Volume :
- 354
- Issue :
- 1
- Database :
- MEDLINE
- Journal :
- Archiv der Pharmazie
- Publication Type :
- Academic Journal
- Accession number :
- 32959443
- Full Text :
- https://doi.org/10.1002/ardp.202000180