Synthesis, characterization, and antimicrobial activity of silver carbene complexes derived from 4,5,6,7-tetrachlorobenzimidazole against antibiotic resistant bacteria
Silver N-heterocyclic carbene complexes have been shown to have great potential as antimicrobial agents, affecting a wide spectrum of both Gram-positive and Gram-negative bacteria. A new series of three silver carbene complexes (SCCs) based on 4,5,6,7-tetrachlorobenzimidazole has been synthesized, c...
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| Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2012-06, Vol.41 (21), p.6500-6506 |
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| container_title | Dalton transactions : an international journal of inorganic chemistry |
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| creator | Wright, Brian D Shah, Parth N McDonald, Lucas J Shaeffer, Michael L Wagers, Patrick O Panzner, Matthew J Smolen, Justin Tagaev, Jasur Tessier, Claire A Cannon, Carolyn L Youngs, Wiley J |
| description | Silver N-heterocyclic carbene complexes have been shown to have great potential as antimicrobial agents, affecting a wide spectrum of both Gram-positive and Gram-negative bacteria. A new series of three silver carbene complexes (SCCs) based on 4,5,6,7-tetrachlorobenzimidazole has been synthesized, characterized, and tested against a panel of clinical strains of bacteria. The imidazolium salts and their precursors were characterized by elemental analysis, mass spectrometry, (1)H and (13)C NMR spectroscopy, and single crystal X-ray diffraction. The silver carbene complexes, SCC32, SCC33, and SCC34 were characterized by elemental analysis, (1)H and (13)C NMR spectroscopy, and single crystal X-ray diffraction. These complexes proved highly efficacious with minimum inhibitory concentrations (MICs) ranging from 0.25 to 6 μg mL(-1). Overall, the complexes were effective against highly resistant bacteria strains, such as methicillin-resistant Staphylococcus aureus (MRSA), weaponizable bacteria, such as Yersinia pestis, and pathogens found within the lungs of cystic fibrosis patients, such as Pseudomonas aeruginosa, Alcaligenes xylosoxidans, and Burkholderia gladioli. SCC33 and SCC34 also showed clinically relevant activity against a silver-resistant strain of Escherichia coli based on MIC testing. |
| doi_str_mv | 10.1039/c2dt00055e |
| format | Article |
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A new series of three silver carbene complexes (SCCs) based on 4,5,6,7-tetrachlorobenzimidazole has been synthesized, characterized, and tested against a panel of clinical strains of bacteria. The imidazolium salts and their precursors were characterized by elemental analysis, mass spectrometry, (1)H and (13)C NMR spectroscopy, and single crystal X-ray diffraction. The silver carbene complexes, SCC32, SCC33, and SCC34 were characterized by elemental analysis, (1)H and (13)C NMR spectroscopy, and single crystal X-ray diffraction. These complexes proved highly efficacious with minimum inhibitory concentrations (MICs) ranging from 0.25 to 6 μg mL(-1). Overall, the complexes were effective against highly resistant bacteria strains, such as methicillin-resistant Staphylococcus aureus (MRSA), weaponizable bacteria, such as Yersinia pestis, and pathogens found within the lungs of cystic fibrosis patients, such as Pseudomonas aeruginosa, Alcaligenes xylosoxidans, and Burkholderia gladioli. 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A new series of three silver carbene complexes (SCCs) based on 4,5,6,7-tetrachlorobenzimidazole has been synthesized, characterized, and tested against a panel of clinical strains of bacteria. The imidazolium salts and their precursors were characterized by elemental analysis, mass spectrometry, (1)H and (13)C NMR spectroscopy, and single crystal X-ray diffraction. The silver carbene complexes, SCC32, SCC33, and SCC34 were characterized by elemental analysis, (1)H and (13)C NMR spectroscopy, and single crystal X-ray diffraction. These complexes proved highly efficacious with minimum inhibitory concentrations (MICs) ranging from 0.25 to 6 μg mL(-1). Overall, the complexes were effective against highly resistant bacteria strains, such as methicillin-resistant Staphylococcus aureus (MRSA), weaponizable bacteria, such as Yersinia pestis, and pathogens found within the lungs of cystic fibrosis patients, such as Pseudomonas aeruginosa, Alcaligenes xylosoxidans, and Burkholderia gladioli. SCC33 and SCC34 also showed clinically relevant activity against a silver-resistant strain of Escherichia coli based on MIC testing.</description><subject>Alcaligenes xylosoxidans</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antiinfectives and antibacterials</subject><subject>Bacteria</subject><subject>Bacteria - drug effects</subject><subject>Benzimidazoles - chemistry</subject><subject>Burkholderia gladioli</subject><subject>Carbenes</subject><subject>Chemistry Techniques, Synthetic</subject><subject>Diffraction</subject><subject>Drug Resistance, Bacterial - drug effects</subject><subject>Escherichia</subject><subject>Methane - analogs & derivatives</subject><subject>Methane - chemistry</subject><subject>Microbial Sensitivity Tests</subject><subject>Organometallic Compounds - chemical synthesis</subject><subject>Organometallic Compounds - chemistry</subject><subject>Organometallic Compounds - pharmacology</subject><subject>Pseudomonas aeruginosa</subject><subject>Silver</subject><subject>Silver - chemistry</subject><subject>Single crystals</subject><subject>Staphylococcus</subject><subject>Strain</subject><subject>X-rays</subject><subject>Yersinia pestis</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFktGO1CAUhhujcdfVGx_AcGlMq0ChlBsTs3HVZBMv1GtyoKc7mLaMwEyceSFfcxlnHfVqEwiE8-fjh_NX1XNGXzPa6jeOD5lSKiU-qM6ZUKrRvBUPT3venVVPUvpOKedU8sfVGeeClqHPq19fdkteYfKpJm4FEVzG6PeQfVhqAstQZvazdzFYDxMpdb_1eUfCSJKfthiJg2hxQeLCvJ7wJyYyFMQWBzLGMBNRy7qrVZMxF_pqCoWEy74wB9iHCQncgF9S_n2R9SF7R-LBUC4HxB4NwdPq0QhTwmd360X17er918uPzfXnD58u3103TgiRG-jFoKjtqOyxU0K3TI9K2ZbCWD6Iq95pBOegdSiVxV5IKyhyGPSomdXYXlRvj9z1xs44OFyK68mso58h7kwAb_6vLH5lbsLWtIq2QqoCeHkHiOHHBlM2s08OpwkWDJtkmBKi6xXr5f1S2XW94ELy-6WUld5q3h2or47S0rKUIo4n84yaQ17M37wU8Yt_n3uS_glIewv-hcBa</recordid><startdate>20120607</startdate><enddate>20120607</enddate><creator>Wright, Brian D</creator><creator>Shah, Parth N</creator><creator>McDonald, Lucas J</creator><creator>Shaeffer, Michael L</creator><creator>Wagers, Patrick O</creator><creator>Panzner, Matthew J</creator><creator>Smolen, Justin</creator><creator>Tagaev, Jasur</creator><creator>Tessier, Claire A</creator><creator>Cannon, Carolyn L</creator><creator>Youngs, Wiley J</creator><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>7X8</scope><scope>7QL</scope><scope>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>JG9</scope><scope>L7M</scope><scope>5PM</scope></search><sort><creationdate>20120607</creationdate><title>Synthesis, characterization, and antimicrobial activity of silver carbene complexes derived from 4,5,6,7-tetrachlorobenzimidazole against antibiotic resistant bacteria</title><author>Wright, Brian D ; Shah, Parth N ; McDonald, Lucas J ; Shaeffer, Michael L ; Wagers, Patrick O ; Panzner, Matthew J ; Smolen, Justin ; Tagaev, Jasur ; Tessier, Claire A ; Cannon, Carolyn L ; Youngs, Wiley J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c444t-a84d70b6058e6749319f77b30af005278c9eacca3ce57be845b40e2ad9f91b9e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Alcaligenes xylosoxidans</topic><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antiinfectives and antibacterials</topic><topic>Bacteria</topic><topic>Bacteria - drug effects</topic><topic>Benzimidazoles - chemistry</topic><topic>Burkholderia gladioli</topic><topic>Carbenes</topic><topic>Chemistry Techniques, Synthetic</topic><topic>Diffraction</topic><topic>Drug Resistance, Bacterial - drug effects</topic><topic>Escherichia</topic><topic>Methane - analogs & derivatives</topic><topic>Methane - chemistry</topic><topic>Microbial Sensitivity Tests</topic><topic>Organometallic Compounds - chemical synthesis</topic><topic>Organometallic Compounds - chemistry</topic><topic>Organometallic Compounds - pharmacology</topic><topic>Pseudomonas aeruginosa</topic><topic>Silver</topic><topic>Silver - chemistry</topic><topic>Single crystals</topic><topic>Staphylococcus</topic><topic>Strain</topic><topic>X-rays</topic><topic>Yersinia pestis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wright, Brian D</creatorcontrib><creatorcontrib>Shah, Parth N</creatorcontrib><creatorcontrib>McDonald, Lucas J</creatorcontrib><creatorcontrib>Shaeffer, Michael L</creatorcontrib><creatorcontrib>Wagers, Patrick O</creatorcontrib><creatorcontrib>Panzner, Matthew J</creatorcontrib><creatorcontrib>Smolen, Justin</creatorcontrib><creatorcontrib>Tagaev, Jasur</creatorcontrib><creatorcontrib>Tessier, Claire A</creatorcontrib><creatorcontrib>Cannon, Carolyn L</creatorcontrib><creatorcontrib>Youngs, Wiley J</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wright, Brian D</au><au>Shah, Parth N</au><au>McDonald, Lucas J</au><au>Shaeffer, Michael L</au><au>Wagers, Patrick O</au><au>Panzner, Matthew J</au><au>Smolen, Justin</au><au>Tagaev, Jasur</au><au>Tessier, Claire A</au><au>Cannon, Carolyn L</au><au>Youngs, Wiley J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, characterization, and antimicrobial activity of silver carbene complexes derived from 4,5,6,7-tetrachlorobenzimidazole against antibiotic resistant bacteria</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2012-06-07</date><risdate>2012</risdate><volume>41</volume><issue>21</issue><spage>6500</spage><epage>6506</epage><pages>6500-6506</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>Silver N-heterocyclic carbene complexes have been shown to have great potential as antimicrobial agents, affecting a wide spectrum of both Gram-positive and Gram-negative bacteria. A new series of three silver carbene complexes (SCCs) based on 4,5,6,7-tetrachlorobenzimidazole has been synthesized, characterized, and tested against a panel of clinical strains of bacteria. The imidazolium salts and their precursors were characterized by elemental analysis, mass spectrometry, (1)H and (13)C NMR spectroscopy, and single crystal X-ray diffraction. The silver carbene complexes, SCC32, SCC33, and SCC34 were characterized by elemental analysis, (1)H and (13)C NMR spectroscopy, and single crystal X-ray diffraction. These complexes proved highly efficacious with minimum inhibitory concentrations (MICs) ranging from 0.25 to 6 μg mL(-1). Overall, the complexes were effective against highly resistant bacteria strains, such as methicillin-resistant Staphylococcus aureus (MRSA), weaponizable bacteria, such as Yersinia pestis, and pathogens found within the lungs of cystic fibrosis patients, such as Pseudomonas aeruginosa, Alcaligenes xylosoxidans, and Burkholderia gladioli. SCC33 and SCC34 also showed clinically relevant activity against a silver-resistant strain of Escherichia coli based on MIC testing.</abstract><cop>England</cop><pmid>22402409</pmid><doi>10.1039/c2dt00055e</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Alcaligenes xylosoxidans Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antiinfectives and antibacterials Bacteria Bacteria - drug effects Benzimidazoles - chemistry Burkholderia gladioli Carbenes Chemistry Techniques, Synthetic Diffraction Drug Resistance, Bacterial - drug effects Escherichia Methane - analogs & derivatives Methane - chemistry Microbial Sensitivity Tests Organometallic Compounds - chemical synthesis Organometallic Compounds - chemistry Organometallic Compounds - pharmacology Pseudomonas aeruginosa Silver Silver - chemistry Single crystals Staphylococcus Strain X-rays Yersinia pestis |
| title | Synthesis, characterization, and antimicrobial activity of silver carbene complexes derived from 4,5,6,7-tetrachlorobenzimidazole against antibiotic resistant bacteria |
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