Novel Phenyl‐Based Bis‐quaternary Ammonium Compounds as Broad‐Spectrum Biocides
Herein we report the synthesis and microbiological evaluation of novel phenyl based bis‐quaternary ammonium compounds (bis‐QACs). Using a simple 2‐step synthetic route from dibromo‐ and dihydroxybenzenes, we obtained a structurally diverse broad panel of bis‐QACs with topologically distinct bridging...
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| Veröffentlicht in: | ChemMedChem 2021-10, Vol.16 (19), p.2954-2959 |
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| creator | Frolov, Nikita A. Fedoseeva, Ksenia A. Hansford, Karl A. Vereshchagin, Anatoly N. |
| description | Herein we report the synthesis and microbiological evaluation of novel phenyl based bis‐quaternary ammonium compounds (bis‐QACs). Using a simple 2‐step synthetic route from dibromo‐ and dihydroxybenzenes, we obtained a structurally diverse broad panel of bis‐QACs with topologically distinct bridging connections between pyridinium heads. Selected analogs possessed potent broad‐spectrum biocidal activity against both bacterial and fungal pathogens: methicillin‐resistant Staphylococcus aureus (ATCC 43300); Escherichia coli (ATCC 25922), Klebsiella pneumonia (ATCC 700603), Acinetobacter baumannii (ATCC 19606), Pseudomonas aeruginosa (ATCC 27853), Candida albicans (ATCC 90028), Cryptococcus neoformans var. grubii (ATCC 208821). Promising compounds displayed minimum inhibitory concentrations (MIC) values ≤0.25 μg/mL alongside improved cytotoxicity and hemolytic profiles compared to modern antiseptics. Thus, synthesized bis‐QACs represent a promising class of biocides with the potential to replace existing household sanitizers.
Bis‐QACs as broad‐spectrum biocides: We report the synthesis and microbiological evaluation of novel phenyl‐based bis‐quaternary ammonium compounds (bis‐QACs). Hit compounds displayed minimum inhibitory concentration (MIC) values ≤0.25 μg/mL on both bacterial and fungal pathogens. |
| doi_str_mv | 10.1002/cmdc.202100284 |
| format | Article |
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Bis‐QACs as broad‐spectrum biocides: We report the synthesis and microbiological evaluation of novel phenyl‐based bis‐quaternary ammonium compounds (bis‐QACs). Hit compounds displayed minimum inhibitory concentration (MIC) values ≤0.25 μg/mL on both bacterial and fungal pathogens.</description><identifier>ISSN: 1860-7179</identifier><identifier>EISSN: 1860-7187</identifier><identifier>DOI: 10.1002/cmdc.202100284</identifier><identifier>PMID: 34252992</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Acinetobacter baumannii - drug effects ; Ammonium ; Ammonium compounds ; Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; antibacterial activity ; antifungal activity ; Antifungal Agents - chemical synthesis ; Antifungal Agents - chemistry ; Antifungal Agents - pharmacology ; Antiseptics ; Bacteria ; Biocides ; Candida albicans - drug effects ; Cryptococcus neoformans - drug effects ; Cytotoxicity ; Dihydroxybenzenes ; Disinfectants - chemical synthesis ; Disinfectants - chemistry ; Disinfectants - pharmacology ; Dose-Response Relationship, Drug ; E coli ; Escherichia coli - drug effects ; Fungi ; Klebsiella ; Klebsiella pneumoniae - drug effects ; Methicillin ; Methicillin-Resistant Staphylococcus aureus - drug effects ; Microbial Sensitivity Tests ; Minimum inhibitory concentration ; Molecular Structure ; Pseudomonas aeruginosa ; Pseudomonas aeruginosa - drug effects ; Pyridinium ; pyridinium salts ; Quaternary ammonium compounds ; Quaternary Ammonium Compounds - chemical synthesis ; Quaternary Ammonium Compounds - chemistry ; Quaternary Ammonium Compounds - pharmacology ; Quaternary ammonium salts ; Sanitizers ; Structure-Activity Relationship ; Toxicity</subject><ispartof>ChemMedChem, 2021-10, Vol.16 (19), p.2954-2959</ispartof><rights>2021 Wiley‐VCH GmbH</rights><rights>2021 Wiley-VCH GmbH.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3734-9ea636fc66bdb8d711338710e226da600b6e25280e4acd570762b4f888400e2e3</citedby><cites>FETCH-LOGICAL-c3734-9ea636fc66bdb8d711338710e226da600b6e25280e4acd570762b4f888400e2e3</cites><orcidid>0000-0001-8675-4943</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcmdc.202100284$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcmdc.202100284$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34252992$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Frolov, Nikita A.</creatorcontrib><creatorcontrib>Fedoseeva, Ksenia A.</creatorcontrib><creatorcontrib>Hansford, Karl A.</creatorcontrib><creatorcontrib>Vereshchagin, Anatoly N.</creatorcontrib><title>Novel Phenyl‐Based Bis‐quaternary Ammonium Compounds as Broad‐Spectrum Biocides</title><title>ChemMedChem</title><addtitle>ChemMedChem</addtitle><description>Herein we report the synthesis and microbiological evaluation of novel phenyl based bis‐quaternary ammonium compounds (bis‐QACs). Using a simple 2‐step synthetic route from dibromo‐ and dihydroxybenzenes, we obtained a structurally diverse broad panel of bis‐QACs with topologically distinct bridging connections between pyridinium heads. Selected analogs possessed potent broad‐spectrum biocidal activity against both bacterial and fungal pathogens: methicillin‐resistant Staphylococcus aureus (ATCC 43300); Escherichia coli (ATCC 25922), Klebsiella pneumonia (ATCC 700603), Acinetobacter baumannii (ATCC 19606), Pseudomonas aeruginosa (ATCC 27853), Candida albicans (ATCC 90028), Cryptococcus neoformans var. grubii (ATCC 208821). Promising compounds displayed minimum inhibitory concentrations (MIC) values ≤0.25 μg/mL alongside improved cytotoxicity and hemolytic profiles compared to modern antiseptics. Thus, synthesized bis‐QACs represent a promising class of biocides with the potential to replace existing household sanitizers.
Bis‐QACs as broad‐spectrum biocides: We report the synthesis and microbiological evaluation of novel phenyl‐based bis‐quaternary ammonium compounds (bis‐QACs). Hit compounds displayed minimum inhibitory concentration (MIC) values ≤0.25 μg/mL on both bacterial and fungal pathogens.</description><subject>Acinetobacter baumannii - drug effects</subject><subject>Ammonium</subject><subject>Ammonium compounds</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>antibacterial activity</subject><subject>antifungal activity</subject><subject>Antifungal Agents - chemical synthesis</subject><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - pharmacology</subject><subject>Antiseptics</subject><subject>Bacteria</subject><subject>Biocides</subject><subject>Candida albicans - drug effects</subject><subject>Cryptococcus neoformans - drug effects</subject><subject>Cytotoxicity</subject><subject>Dihydroxybenzenes</subject><subject>Disinfectants - chemical synthesis</subject><subject>Disinfectants - chemistry</subject><subject>Disinfectants - pharmacology</subject><subject>Dose-Response Relationship, Drug</subject><subject>E coli</subject><subject>Escherichia coli - drug effects</subject><subject>Fungi</subject><subject>Klebsiella</subject><subject>Klebsiella pneumoniae - drug effects</subject><subject>Methicillin</subject><subject>Methicillin-Resistant Staphylococcus aureus - drug effects</subject><subject>Microbial Sensitivity Tests</subject><subject>Minimum inhibitory concentration</subject><subject>Molecular Structure</subject><subject>Pseudomonas aeruginosa</subject><subject>Pseudomonas aeruginosa - drug effects</subject><subject>Pyridinium</subject><subject>pyridinium salts</subject><subject>Quaternary ammonium compounds</subject><subject>Quaternary Ammonium Compounds - chemical synthesis</subject><subject>Quaternary Ammonium Compounds - chemistry</subject><subject>Quaternary Ammonium Compounds - pharmacology</subject><subject>Quaternary ammonium salts</subject><subject>Sanitizers</subject><subject>Structure-Activity Relationship</subject><subject>Toxicity</subject><issn>1860-7179</issn><issn>1860-7187</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0LtOwzAUBmALgSgUVkYUiYWl5dhObWek4SqViwSdI8c-FamSuMQNqBuPwDPyJLhqKRILk4_lz7_sn5AjCn0KwM5MZU2fAVtuVLxF9qgS0JNUye3NLJMO2fd-ChDHiqpd0uExG7AkYXtkfO_esIweX7BelF8fn0Pt0UbDwof5tdVzbGrdLKLzqnJ10VZR6qqZa2vrI-2jYeO0DfBphmbehNNh4Uxh0R-QnYkuPR6u1y4ZX10-pze90cP1bXo-6hkuedxLUAsuJkaI3ObKSko5V5ICMiasFgC5wPBQBRhrYwcSpGB5PFFKxRAQ8i45XeXOGvfaop9nVeENlqWu0bU-Y4MBZZAA8EBP_tCpa8PnyqWSCadCSBlUf6VM47xvcJLNmqIKDWQUsmXH2bLwbFN4uHC8jm3zCu2G_zQcQLIC70WJi3_isvTuIv0N_wZWA44I</recordid><startdate>20211006</startdate><enddate>20211006</enddate><creator>Frolov, Nikita A.</creator><creator>Fedoseeva, Ksenia A.</creator><creator>Hansford, Karl A.</creator><creator>Vereshchagin, Anatoly N.</creator><general>Wiley Subscription Services, 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>7QO</scope><scope>7TK</scope><scope>7U7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>K9.</scope><scope>P64</scope><scope>RC3</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-8675-4943</orcidid></search><sort><creationdate>20211006</creationdate><title>Novel Phenyl‐Based Bis‐quaternary Ammonium Compounds as Broad‐Spectrum Biocides</title><author>Frolov, Nikita A. ; Fedoseeva, Ksenia A. ; Hansford, Karl A. ; Vereshchagin, Anatoly N.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3734-9ea636fc66bdb8d711338710e226da600b6e25280e4acd570762b4f888400e2e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Acinetobacter baumannii - drug effects</topic><topic>Ammonium</topic><topic>Ammonium compounds</topic><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>antibacterial activity</topic><topic>antifungal activity</topic><topic>Antifungal Agents - chemical synthesis</topic><topic>Antifungal Agents - chemistry</topic><topic>Antifungal Agents - pharmacology</topic><topic>Antiseptics</topic><topic>Bacteria</topic><topic>Biocides</topic><topic>Candida albicans - drug effects</topic><topic>Cryptococcus neoformans - drug effects</topic><topic>Cytotoxicity</topic><topic>Dihydroxybenzenes</topic><topic>Disinfectants - chemical synthesis</topic><topic>Disinfectants - chemistry</topic><topic>Disinfectants - pharmacology</topic><topic>Dose-Response Relationship, Drug</topic><topic>E coli</topic><topic>Escherichia coli - drug effects</topic><topic>Fungi</topic><topic>Klebsiella</topic><topic>Klebsiella pneumoniae - drug effects</topic><topic>Methicillin</topic><topic>Methicillin-Resistant Staphylococcus aureus - drug effects</topic><topic>Microbial Sensitivity Tests</topic><topic>Minimum inhibitory concentration</topic><topic>Molecular Structure</topic><topic>Pseudomonas aeruginosa</topic><topic>Pseudomonas aeruginosa - drug effects</topic><topic>Pyridinium</topic><topic>pyridinium salts</topic><topic>Quaternary ammonium compounds</topic><topic>Quaternary Ammonium Compounds - chemical synthesis</topic><topic>Quaternary Ammonium Compounds - chemistry</topic><topic>Quaternary Ammonium Compounds - pharmacology</topic><topic>Quaternary ammonium salts</topic><topic>Sanitizers</topic><topic>Structure-Activity Relationship</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Frolov, Nikita A.</creatorcontrib><creatorcontrib>Fedoseeva, Ksenia A.</creatorcontrib><creatorcontrib>Hansford, Karl A.</creatorcontrib><creatorcontrib>Vereshchagin, Anatoly N.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Neurosciences Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Genetics Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>ChemMedChem</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Frolov, Nikita A.</au><au>Fedoseeva, Ksenia A.</au><au>Hansford, Karl A.</au><au>Vereshchagin, Anatoly N.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel Phenyl‐Based Bis‐quaternary Ammonium Compounds as Broad‐Spectrum Biocides</atitle><jtitle>ChemMedChem</jtitle><addtitle>ChemMedChem</addtitle><date>2021-10-06</date><risdate>2021</risdate><volume>16</volume><issue>19</issue><spage>2954</spage><epage>2959</epage><pages>2954-2959</pages><issn>1860-7179</issn><eissn>1860-7187</eissn><abstract>Herein we report the synthesis and microbiological evaluation of novel phenyl based bis‐quaternary ammonium compounds (bis‐QACs). Using a simple 2‐step synthetic route from dibromo‐ and dihydroxybenzenes, we obtained a structurally diverse broad panel of bis‐QACs with topologically distinct bridging connections between pyridinium heads. Selected analogs possessed potent broad‐spectrum biocidal activity against both bacterial and fungal pathogens: methicillin‐resistant Staphylococcus aureus (ATCC 43300); Escherichia coli (ATCC 25922), Klebsiella pneumonia (ATCC 700603), Acinetobacter baumannii (ATCC 19606), Pseudomonas aeruginosa (ATCC 27853), Candida albicans (ATCC 90028), Cryptococcus neoformans var. grubii (ATCC 208821). Promising compounds displayed minimum inhibitory concentrations (MIC) values ≤0.25 μg/mL alongside improved cytotoxicity and hemolytic profiles compared to modern antiseptics. Thus, synthesized bis‐QACs represent a promising class of biocides with the potential to replace existing household sanitizers.
Bis‐QACs as broad‐spectrum biocides: We report the synthesis and microbiological evaluation of novel phenyl‐based bis‐quaternary ammonium compounds (bis‐QACs). Hit compounds displayed minimum inhibitory concentration (MIC) values ≤0.25 μg/mL on both bacterial and fungal pathogens.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>34252992</pmid><doi>10.1002/cmdc.202100284</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-8675-4943</orcidid></addata></record> |
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| subjects | Acinetobacter baumannii - drug effects Ammonium Ammonium compounds Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology antibacterial activity antifungal activity Antifungal Agents - chemical synthesis Antifungal Agents - chemistry Antifungal Agents - pharmacology Antiseptics Bacteria Biocides Candida albicans - drug effects Cryptococcus neoformans - drug effects Cytotoxicity Dihydroxybenzenes Disinfectants - chemical synthesis Disinfectants - chemistry Disinfectants - pharmacology Dose-Response Relationship, Drug E coli Escherichia coli - drug effects Fungi Klebsiella Klebsiella pneumoniae - drug effects Methicillin Methicillin-Resistant Staphylococcus aureus - drug effects Microbial Sensitivity Tests Minimum inhibitory concentration Molecular Structure Pseudomonas aeruginosa Pseudomonas aeruginosa - drug effects Pyridinium pyridinium salts Quaternary ammonium compounds Quaternary Ammonium Compounds - chemical synthesis Quaternary Ammonium Compounds - chemistry Quaternary Ammonium Compounds - pharmacology Quaternary ammonium salts Sanitizers Structure-Activity Relationship Toxicity |
| title | Novel Phenyl‐Based Bis‐quaternary Ammonium Compounds as Broad‐Spectrum Biocides |
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