Mechanism of Antibacterial and Degradation Behavior of a Chlorinated Isoxazolylnaphthoquinone

The chemical stability of 3-chloro-2-hydroxy-(3,4-dimethyl-5-isoxazolyl)-1,4-naphthoquinon-4-imine (ClQ1), a new potential antimicrobial agent was analyzed at different pH values by first-derivative spectroscopy. The degradation of ClQ1 followed a pseudo-first-order kinetics in aqueous media at diff...

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Bibliographic Details
Published in:Biochemical and biophysical research communications 1999-09, Vol.263 (2), p.301-307
Main Authors: Bogdanov, Patricia M, Dabbene, Viviana G, Albesa, Inés, de Bertorello, Marı́a M, Briñón, Margarita C
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - metabolism
Anti-Bacterial Agents - pharmacology
antibacterial activity
chlorinated naphthoquinonimine
Chlorine
Drug Stability
Electron Transport - drug effects
Gram-Negative Aerobic Rods and Cocci - drug effects
Hydrogen-Ion Concentration
Hydrolysis
Isoxazoles - chemistry
Isoxazoles - metabolism
Isoxazoles - pharmacology
Microbial Sensitivity Tests
Naphthoquinones - chemistry
Naphthoquinones - metabolism
Naphthoquinones - pharmacology
stability studies
Staphylococcus - drug effects
Staphylococcus aureus
Structure-Activity Relationship
superoxide anion
Superoxides - metabolism
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Summary:The chemical stability of 3-chloro-2-hydroxy-(3,4-dimethyl-5-isoxazolyl)-1,4-naphthoquinon-4-imine (ClQ1), a new potential antimicrobial agent was analyzed at different pH values by first-derivative spectroscopy. The degradation of ClQ1 followed a pseudo-first-order kinetics in aqueous media at different pH values. The interaction of antibiotics with respiratory chain of Staphylococcus aureus generates superoxide anion, an oxygen radical capable of producing damage to the bacteria. The performed assays have demonstrated that ClQ1 presents higher activity and toxic oxidant generation at pH 5.0 than at pH 7.5. In addition, the antibacterial activity of other halogenated isoxazolylnaphthoquinones was also studied in different collection and clinical strains which presented the following decreasing activity, ClQ1 > BrQ1 > DClQ1 whereas DBrQ1 did not show inhibition properties. The antibacterial and stability properties evidenced by ClQ1 are so important that must be taken into account when new alternative treatments against β-lactamase-positive S. aureus strains are investigated.
ISSN:0006-291X
1090-2104
DOI:10.1006/bbrc.1999.1360