Discovery of sulfone containing metallo-β-lactamase inhibitors with reduced bacterial cell efflux and histamine release issues
[Display omitted] •Gram-Negative Bacterial Coverage.•Anti-bacterial Resistance.•Sulfone Containing Drug.•Histamine Release.•Enzyme-Inhibitor X- Ray Co-Structure. The design, syntheses and antibacterial evaluation of sulfone analogues of previously disclosed metallo-β-lactamase inhibitors (MBLis) are...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2024-12, Vol.114, p.129989, Article 129989 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Bennett, Frank Huang, Yuhua Dong, Shuzhi Jiang, Jinlong Hunter, David Zhao, Zhiqiang Gu, Xin Scott, Jack D. Tang, Haiqun Yang, Dexi Xiao, Li Scapin, Giovanna Fischmann, Thierry Mirza, Asra Dayananth, Priya Painter, Ronald E. Villafania, Artjohn Garlisi, Charles G. Zhang, Rumin Mayhood, Todd W. Si, Qian Li, Nianyu Amin, Rupesh P. Chen, Feifei Bhatt, Bhavana Regan, Christopher P. Regan, Hilary Lin, Xinjie Wu, Jin Leithead, Andrew Young, Katherine Pasternak, Alexander |
| description | [Display omitted]
•Gram-Negative Bacterial Coverage.•Anti-bacterial Resistance.•Sulfone Containing Drug.•Histamine Release.•Enzyme-Inhibitor X- Ray Co-Structure.
The design, syntheses and antibacterial evaluation of sulfone analogues of previously disclosed metallo-β-lactamase inhibitors (MBLis) are described. The novel derivatives were overall more effective in gram-negative bacterial cell-based assays when combined with imipenem and relebactam. The major contributors to the improved anti-bacterial activity are enhanced enzyme-inhibitor interactions and reduced bacterial cell efflux monitored via an efflux assay involving isogenic Pseudomonas aeruginosa efflux + and efflux – tool strains. |
| doi_str_mv | 10.1016/j.bmcl.2024.129989 |
| format | Article |
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•Gram-Negative Bacterial Coverage.•Anti-bacterial Resistance.•Sulfone Containing Drug.•Histamine Release.•Enzyme-Inhibitor X- Ray Co-Structure.
The design, syntheses and antibacterial evaluation of sulfone analogues of previously disclosed metallo-β-lactamase inhibitors (MBLis) are described. The novel derivatives were overall more effective in gram-negative bacterial cell-based assays when combined with imipenem and relebactam. The major contributors to the improved anti-bacterial activity are enhanced enzyme-inhibitor interactions and reduced bacterial cell efflux monitored via an efflux assay involving isogenic Pseudomonas aeruginosa efflux + and efflux – tool strains.</description><identifier>ISSN: 0960-894X</identifier><identifier>ISSN: 1464-3405</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2024.129989</identifier><identifier>PMID: 39396683</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Anti-bacterial ; Metallo-β-lactamase ; Sulfone ; β-lactamase</subject><ispartof>Bioorganic & medicinal chemistry letters, 2024-12, Vol.114, p.129989, Article 129989</ispartof><rights>2024 Elsevier Ltd</rights><rights>Copyright © 2024 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c237t-39aee2c0813c966082f6be7d6d2705f8021d95fbfc9ffa912fdfc08bb0a9a883</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2024.129989$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,782,786,3554,27933,27934,46004</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/39396683$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bennett, Frank</creatorcontrib><creatorcontrib>Huang, Yuhua</creatorcontrib><creatorcontrib>Dong, Shuzhi</creatorcontrib><creatorcontrib>Jiang, Jinlong</creatorcontrib><creatorcontrib>Hunter, David</creatorcontrib><creatorcontrib>Zhao, Zhiqiang</creatorcontrib><creatorcontrib>Gu, Xin</creatorcontrib><creatorcontrib>Scott, Jack D.</creatorcontrib><creatorcontrib>Tang, Haiqun</creatorcontrib><creatorcontrib>Yang, Dexi</creatorcontrib><creatorcontrib>Xiao, Li</creatorcontrib><creatorcontrib>Scapin, Giovanna</creatorcontrib><creatorcontrib>Fischmann, Thierry</creatorcontrib><creatorcontrib>Mirza, Asra</creatorcontrib><creatorcontrib>Dayananth, Priya</creatorcontrib><creatorcontrib>Painter, Ronald E.</creatorcontrib><creatorcontrib>Villafania, Artjohn</creatorcontrib><creatorcontrib>Garlisi, Charles G.</creatorcontrib><creatorcontrib>Zhang, Rumin</creatorcontrib><creatorcontrib>Mayhood, Todd W.</creatorcontrib><creatorcontrib>Si, Qian</creatorcontrib><creatorcontrib>Li, Nianyu</creatorcontrib><creatorcontrib>Amin, Rupesh P.</creatorcontrib><creatorcontrib>Chen, Feifei</creatorcontrib><creatorcontrib>Bhatt, Bhavana</creatorcontrib><creatorcontrib>Regan, Christopher P.</creatorcontrib><creatorcontrib>Regan, Hilary</creatorcontrib><creatorcontrib>Lin, Xinjie</creatorcontrib><creatorcontrib>Wu, Jin</creatorcontrib><creatorcontrib>Leithead, Andrew</creatorcontrib><creatorcontrib>Young, Katherine</creatorcontrib><creatorcontrib>Pasternak, Alexander</creatorcontrib><title>Discovery of sulfone containing metallo-β-lactamase inhibitors with reduced bacterial cell efflux and histamine release issues</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
•Gram-Negative Bacterial Coverage.•Anti-bacterial Resistance.•Sulfone Containing Drug.•Histamine Release.•Enzyme-Inhibitor X- Ray Co-Structure.
The design, syntheses and antibacterial evaluation of sulfone analogues of previously disclosed metallo-β-lactamase inhibitors (MBLis) are described. The novel derivatives were overall more effective in gram-negative bacterial cell-based assays when combined with imipenem and relebactam. The major contributors to the improved anti-bacterial activity are enhanced enzyme-inhibitor interactions and reduced bacterial cell efflux monitored via an efflux assay involving isogenic Pseudomonas aeruginosa efflux + and efflux – tool strains.</description><subject>Anti-bacterial</subject><subject>Metallo-β-lactamase</subject><subject>Sulfone</subject><subject>β-lactamase</subject><issn>0960-894X</issn><issn>1464-3405</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp9kLtuGzEQRYnARiQ_fsCFwdLNKnxpRQJpAid-AAbcqHBHcMlhRIG7dMhdO67yT_mQfJOpyEnpappz78wchM4oWVBC20_bRdfbuGCEiQVlSkn1Ac2paEXDBVkeoDlRLWmkEg8zdFTKlhAqiBAf0YwrrtpW8jn69TUUm54gv-DkcZmiTwNgm4bRhCEM33EPo4kxNX9-N9HY0fSmAA7DJnRhTLng5zBucAY3WXC4qwTkYCK2ECMG7-P0E5vB4U0oNRtqd4YIfztKmaCcoENvYoHTt3mM1lff1pc3zd399e3ll7vGMr4aG64MALNEUm7r5UQy33awcq1jK7L0kjDq1NJ33irvjaLMO1_priNGGSn5MbrY1z7m9KOuHXVf_643mgHSVDSntOVcLKWqKNujNqdSMnj9mENv8oumRO-8663eedc773rvvYbO3_qnrgf3P_JPdAU-7wGoTz4FyLrYAEOVFjLYUbsU3ut_BXjDmFU</recordid><startdate>20241201</startdate><enddate>20241201</enddate><creator>Bennett, Frank</creator><creator>Huang, Yuhua</creator><creator>Dong, Shuzhi</creator><creator>Jiang, Jinlong</creator><creator>Hunter, David</creator><creator>Zhao, Zhiqiang</creator><creator>Gu, Xin</creator><creator>Scott, Jack D.</creator><creator>Tang, Haiqun</creator><creator>Yang, Dexi</creator><creator>Xiao, Li</creator><creator>Scapin, Giovanna</creator><creator>Fischmann, Thierry</creator><creator>Mirza, Asra</creator><creator>Dayananth, Priya</creator><creator>Painter, Ronald E.</creator><creator>Villafania, Artjohn</creator><creator>Garlisi, Charles G.</creator><creator>Zhang, Rumin</creator><creator>Mayhood, Todd W.</creator><creator>Si, Qian</creator><creator>Li, Nianyu</creator><creator>Amin, Rupesh P.</creator><creator>Chen, Feifei</creator><creator>Bhatt, Bhavana</creator><creator>Regan, Christopher P.</creator><creator>Regan, Hilary</creator><creator>Lin, Xinjie</creator><creator>Wu, Jin</creator><creator>Leithead, Andrew</creator><creator>Young, Katherine</creator><creator>Pasternak, Alexander</creator><general>Elsevier Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20241201</creationdate><title>Discovery of sulfone containing metallo-β-lactamase inhibitors with reduced bacterial cell efflux and histamine release issues</title><author>Bennett, Frank ; Huang, Yuhua ; Dong, Shuzhi ; Jiang, Jinlong ; Hunter, David ; Zhao, Zhiqiang ; Gu, Xin ; Scott, Jack D. ; Tang, Haiqun ; Yang, Dexi ; Xiao, Li ; Scapin, Giovanna ; Fischmann, Thierry ; Mirza, Asra ; Dayananth, Priya ; Painter, Ronald E. ; Villafania, Artjohn ; Garlisi, Charles G. ; Zhang, Rumin ; Mayhood, Todd W. ; Si, Qian ; Li, Nianyu ; Amin, Rupesh P. ; Chen, Feifei ; Bhatt, Bhavana ; Regan, Christopher P. ; Regan, Hilary ; Lin, Xinjie ; Wu, Jin ; Leithead, Andrew ; Young, Katherine ; Pasternak, Alexander</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c237t-39aee2c0813c966082f6be7d6d2705f8021d95fbfc9ffa912fdfc08bb0a9a883</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Anti-bacterial</topic><topic>Metallo-β-lactamase</topic><topic>Sulfone</topic><topic>β-lactamase</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bennett, Frank</creatorcontrib><creatorcontrib>Huang, Yuhua</creatorcontrib><creatorcontrib>Dong, Shuzhi</creatorcontrib><creatorcontrib>Jiang, Jinlong</creatorcontrib><creatorcontrib>Hunter, David</creatorcontrib><creatorcontrib>Zhao, Zhiqiang</creatorcontrib><creatorcontrib>Gu, Xin</creatorcontrib><creatorcontrib>Scott, Jack D.</creatorcontrib><creatorcontrib>Tang, Haiqun</creatorcontrib><creatorcontrib>Yang, Dexi</creatorcontrib><creatorcontrib>Xiao, Li</creatorcontrib><creatorcontrib>Scapin, Giovanna</creatorcontrib><creatorcontrib>Fischmann, Thierry</creatorcontrib><creatorcontrib>Mirza, Asra</creatorcontrib><creatorcontrib>Dayananth, Priya</creatorcontrib><creatorcontrib>Painter, Ronald E.</creatorcontrib><creatorcontrib>Villafania, Artjohn</creatorcontrib><creatorcontrib>Garlisi, Charles G.</creatorcontrib><creatorcontrib>Zhang, Rumin</creatorcontrib><creatorcontrib>Mayhood, Todd W.</creatorcontrib><creatorcontrib>Si, Qian</creatorcontrib><creatorcontrib>Li, Nianyu</creatorcontrib><creatorcontrib>Amin, Rupesh P.</creatorcontrib><creatorcontrib>Chen, Feifei</creatorcontrib><creatorcontrib>Bhatt, Bhavana</creatorcontrib><creatorcontrib>Regan, Christopher P.</creatorcontrib><creatorcontrib>Regan, Hilary</creatorcontrib><creatorcontrib>Lin, Xinjie</creatorcontrib><creatorcontrib>Wu, Jin</creatorcontrib><creatorcontrib>Leithead, Andrew</creatorcontrib><creatorcontrib>Young, Katherine</creatorcontrib><creatorcontrib>Pasternak, Alexander</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bennett, Frank</au><au>Huang, Yuhua</au><au>Dong, Shuzhi</au><au>Jiang, Jinlong</au><au>Hunter, David</au><au>Zhao, Zhiqiang</au><au>Gu, Xin</au><au>Scott, Jack D.</au><au>Tang, Haiqun</au><au>Yang, Dexi</au><au>Xiao, Li</au><au>Scapin, Giovanna</au><au>Fischmann, Thierry</au><au>Mirza, Asra</au><au>Dayananth, Priya</au><au>Painter, Ronald E.</au><au>Villafania, Artjohn</au><au>Garlisi, Charles G.</au><au>Zhang, Rumin</au><au>Mayhood, Todd W.</au><au>Si, Qian</au><au>Li, Nianyu</au><au>Amin, Rupesh P.</au><au>Chen, Feifei</au><au>Bhatt, Bhavana</au><au>Regan, Christopher P.</au><au>Regan, Hilary</au><au>Lin, Xinjie</au><au>Wu, Jin</au><au>Leithead, Andrew</au><au>Young, Katherine</au><au>Pasternak, Alexander</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Discovery of sulfone containing metallo-β-lactamase inhibitors with reduced bacterial cell efflux and histamine release issues</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2024-12-01</date><risdate>2024</risdate><volume>114</volume><spage>129989</spage><pages>129989-</pages><artnum>129989</artnum><issn>0960-894X</issn><issn>1464-3405</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
•Gram-Negative Bacterial Coverage.•Anti-bacterial Resistance.•Sulfone Containing Drug.•Histamine Release.•Enzyme-Inhibitor X- Ray Co-Structure.
The design, syntheses and antibacterial evaluation of sulfone analogues of previously disclosed metallo-β-lactamase inhibitors (MBLis) are described. The novel derivatives were overall more effective in gram-negative bacterial cell-based assays when combined with imipenem and relebactam. The major contributors to the improved anti-bacterial activity are enhanced enzyme-inhibitor interactions and reduced bacterial cell efflux monitored via an efflux assay involving isogenic Pseudomonas aeruginosa efflux + and efflux – tool strains.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>39396683</pmid><doi>10.1016/j.bmcl.2024.129989</doi></addata></record> |
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| subjects | Anti-bacterial Metallo-β-lactamase Sulfone β-lactamase |
| title | Discovery of sulfone containing metallo-β-lactamase inhibitors with reduced bacterial cell efflux and histamine release issues |
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