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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| Veröffentlicht in: | Biochemical and biophysical research communications 1999-09, Vol.263 (2), p.301-307 |
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| container_title | Biochemical and biophysical research communications |
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| creator | Bogdanov, Patricia M Dabbene, Viviana G Albesa, Inés de Bertorello, Marı́a M Briñón, Margarita C |
| description | 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. |
| doi_str_mv | 10.1006/bbrc.1999.1360 |
| format | Article |
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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.</description><identifier>ISSN: 0006-291X</identifier><identifier>EISSN: 1090-2104</identifier><identifier>DOI: 10.1006/bbrc.1999.1360</identifier><identifier>PMID: 10491288</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>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</subject><ispartof>Biochemical and biophysical research communications, 1999-09, Vol.263 (2), p.301-307</ispartof><rights>1999 Academic Press</rights><rights>Copyright 1999 Academic Press.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c371t-c07223ec6924b11c0e564d4edbbf4b4eb55acf6cb7c0c4f34a28cd0e2f44c63b3</citedby><cites>FETCH-LOGICAL-c371t-c07223ec6924b11c0e564d4edbbf4b4eb55acf6cb7c0c4f34a28cd0e2f44c63b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1006/bbrc.1999.1360$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27922,27923,45993</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10491288$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bogdanov, Patricia M</creatorcontrib><creatorcontrib>Dabbene, Viviana G</creatorcontrib><creatorcontrib>Albesa, Inés</creatorcontrib><creatorcontrib>de Bertorello, Marı́a M</creatorcontrib><creatorcontrib>Briñón, Margarita C</creatorcontrib><title>Mechanism of Antibacterial and Degradation Behavior of a Chlorinated Isoxazolylnaphthoquinone</title><title>Biochemical and biophysical research communications</title><addtitle>Biochem Biophys Res Commun</addtitle><description>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.</description><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - metabolism</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>antibacterial activity</subject><subject>chlorinated naphthoquinonimine</subject><subject>Chlorine</subject><subject>Drug Stability</subject><subject>Electron Transport - drug effects</subject><subject>Gram-Negative Aerobic Rods and Cocci - drug effects</subject><subject>Hydrogen-Ion Concentration</subject><subject>Hydrolysis</subject><subject>Isoxazoles - chemistry</subject><subject>Isoxazoles - metabolism</subject><subject>Isoxazoles - pharmacology</subject><subject>Microbial Sensitivity Tests</subject><subject>Naphthoquinones - chemistry</subject><subject>Naphthoquinones - metabolism</subject><subject>Naphthoquinones - pharmacology</subject><subject>stability studies</subject><subject>Staphylococcus - drug effects</subject><subject>Staphylococcus aureus</subject><subject>Structure-Activity Relationship</subject><subject>superoxide anion</subject><subject>Superoxides - metabolism</subject><issn>0006-291X</issn><issn>1090-2104</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kD1PwzAQhi0EoqWwMqJMbCm247rJWMqnBGIBiQVZ9vlCjFK72CkCfj2JysDCdMM973u6h5BjRqeMUnlmTIQpq6pqygpJd8iY0YrmnFGxS8a0J3JesecROUjpjVLGhKz2yahfV4yX5Zi83CM02ru0ykKdLXznjIYOo9Ntpr3NLvA1aqs7F3x2jo3-cCEOpM6WTRui87pDm92m8Km_Q_vVer1uuia8b5wPHg_JXq3bhEe_c0Keri4flzf53cP17XJxl0MxZ10OdM55gSArLgxjQHEmhRVojamFEWhmMw21BDMHCqIuhOYlWIq8FgJkYYoJOd32rmN_GlOnVi4Btq32GDZJsXnBZSHLHpxuQYghpYi1Wke30vFLMaoGoWoQqgahahDaB05-mzdmhfYPvjXYA-UWwP6_D4dRJXDoAa2LCJ2ywf3X_QP2BocJ</recordid><startdate>19990924</startdate><enddate>19990924</enddate><creator>Bogdanov, Patricia M</creator><creator>Dabbene, Viviana G</creator><creator>Albesa, Inés</creator><creator>de Bertorello, Marı́a M</creator><creator>Briñón, Margarita C</creator><general>Elsevier Inc</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>19990924</creationdate><title>Mechanism of Antibacterial and Degradation Behavior of a Chlorinated Isoxazolylnaphthoquinone</title><author>Bogdanov, Patricia M ; 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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. 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| 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 |
| title | Mechanism of Antibacterial and Degradation Behavior of a Chlorinated Isoxazolylnaphthoquinone |
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