Targeting quorum sensing by designing azoline derivatives to inhibit the N-hexanoyl homoserine lactone-receptor CviR: Synthesis as well as biological and theoretical evaluations
[Display omitted] To counteract bacterial resistance, we investigated the interruption of quorum sensing mediated by non-classical bioisosteres of the N-hexanoyl homoserine lactone with an azoline core. For this purpose, a set of selected 2-substituted azolines was synthesized, establishing the basi...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2015-12, Vol.23 (24), p.7565-7577 |
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| creator | Bucio-Cano, Alejandro Reyes-Arellano, Alicia Correa-Basurto, José Bello, Martiniano Torres-Jaramillo, Jenifer Salgado-Zamora, Héctor Curiel-Quesada, Everardo Peralta-Cruz, Javier Avila-Sorrosa, Alcives |
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To counteract bacterial resistance, we investigated the interruption of quorum sensing mediated by non-classical bioisosteres of the N-hexanoyl homoserine lactone with an azoline core. For this purpose, a set of selected 2-substituted azolines was synthesized, establishing the basis for a new protocol to synthesize 2-amino imidazolines. The synthesized compounds were evaluated as inhibitors of violacein production in Chromobacterium violaceum. Theoretical studies on bioisostere–protein interactions were performed using CviR. The results show that some azolines decreased violacein production, suggesting an antiquorum sensing profile against Gram-negative bacteria. Docking and molecular dynamic simulations together with binding free energy calculations revealed the exact binding and inhibitory profiles. These theoretical results show relationship with the in vitro activity of the azoline series. |
| doi_str_mv | 10.1016/j.bmc.2015.10.046 |
| format | Article |
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To counteract bacterial resistance, we investigated the interruption of quorum sensing mediated by non-classical bioisosteres of the N-hexanoyl homoserine lactone with an azoline core. For this purpose, a set of selected 2-substituted azolines was synthesized, establishing the basis for a new protocol to synthesize 2-amino imidazolines. The synthesized compounds were evaluated as inhibitors of violacein production in Chromobacterium violaceum. Theoretical studies on bioisostere–protein interactions were performed using CviR. The results show that some azolines decreased violacein production, suggesting an antiquorum sensing profile against Gram-negative bacteria. Docking and molecular dynamic simulations together with binding free energy calculations revealed the exact binding and inhibitory profiles. These theoretical results show relationship with the in vitro activity of the azoline series.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2015.10.046</identifier><identifier>PMID: 26654469</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>4-Butyrolactone - analogs & derivatives ; 4-Butyrolactone - chemistry ; 4-Butyrolactone - pharmacology ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Azolines ; Bacterial Proteins - antagonists & inhibitors ; Bacterial Proteins - metabolism ; Chromobacterium - drug effects ; Chromobacterium - physiology ; Chromobacterium violaceum ; Cinoxacin - chemistry ; Cinoxacin - pharmacology ; Molecular dynamic simulation ; Molecular Dynamics Simulation ; Non classical bioisosteres ; Quorum sensing ; Quorum Sensing - drug effects</subject><ispartof>Bioorganic & medicinal chemistry, 2015-12, Vol.23 (24), p.7565-7577</ispartof><rights>2015 The Authors</rights><rights>Copyright © 2015 The Authors. Published by Elsevier Ltd.. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c396t-1d3598326b410ea992bb2798ee297a09884ae2ad4241ad605b4e643fa227e69e3</citedby><cites>FETCH-LOGICAL-c396t-1d3598326b410ea992bb2798ee297a09884ae2ad4241ad605b4e643fa227e69e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2015.10.046$$EHTML$$P50$$Gelsevier$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26654469$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bucio-Cano, Alejandro</creatorcontrib><creatorcontrib>Reyes-Arellano, Alicia</creatorcontrib><creatorcontrib>Correa-Basurto, José</creatorcontrib><creatorcontrib>Bello, Martiniano</creatorcontrib><creatorcontrib>Torres-Jaramillo, Jenifer</creatorcontrib><creatorcontrib>Salgado-Zamora, Héctor</creatorcontrib><creatorcontrib>Curiel-Quesada, Everardo</creatorcontrib><creatorcontrib>Peralta-Cruz, Javier</creatorcontrib><creatorcontrib>Avila-Sorrosa, Alcives</creatorcontrib><title>Targeting quorum sensing by designing azoline derivatives to inhibit the N-hexanoyl homoserine lactone-receptor CviR: Synthesis as well as biological and theoretical evaluations</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>[Display omitted]
To counteract bacterial resistance, we investigated the interruption of quorum sensing mediated by non-classical bioisosteres of the N-hexanoyl homoserine lactone with an azoline core. For this purpose, a set of selected 2-substituted azolines was synthesized, establishing the basis for a new protocol to synthesize 2-amino imidazolines. The synthesized compounds were evaluated as inhibitors of violacein production in Chromobacterium violaceum. Theoretical studies on bioisostere–protein interactions were performed using CviR. The results show that some azolines decreased violacein production, suggesting an antiquorum sensing profile against Gram-negative bacteria. Docking and molecular dynamic simulations together with binding free energy calculations revealed the exact binding and inhibitory profiles. These theoretical results show relationship with the in vitro activity of the azoline series.</description><subject>4-Butyrolactone - analogs & derivatives</subject><subject>4-Butyrolactone - chemistry</subject><subject>4-Butyrolactone - pharmacology</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Azolines</subject><subject>Bacterial Proteins - antagonists & inhibitors</subject><subject>Bacterial Proteins - metabolism</subject><subject>Chromobacterium - drug effects</subject><subject>Chromobacterium - physiology</subject><subject>Chromobacterium violaceum</subject><subject>Cinoxacin - chemistry</subject><subject>Cinoxacin - pharmacology</subject><subject>Molecular dynamic simulation</subject><subject>Molecular Dynamics Simulation</subject><subject>Non classical bioisosteres</subject><subject>Quorum sensing</subject><subject>Quorum Sensing - drug effects</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9UU1vEzEUtBAVTQs_gAvykcsG2-t11nBCEbRIVZGgnC3b-5I42rVT27sl_Kv-Q7ykcOT0NE8z8z4GodeULCmh4t1-aQa7ZIQ2BS8JF8_QgnLBq7qW9DlaECnairRSnKOLlPaEEMYlfYHOmRAN50Iu0OOdjlvIzm_x_RjiOOAEPs3QHHEHyW39DPSv0DsPpRPdpLObIOEcsPM7Z1zGeQf4ttrBT-3Dsce7MIRUmEXQa5uDhyqChUMOEa8n9-09_n70RZNcwjrhB-j7uRoX-rB1Vhfku9k0xLLajGHS_VjmBp9eorON7hO8eqqX6MfnT3fr6-rm69WX9cebytZS5Ip2dSPbmgnDKQEtJTOGrWQLwORKE9m2XAPTHWec6k6QxnAQvN5oxlYgJNSX6O3J9xDD_Qgpq8ElW1bVHsKYFF01hNeScVGo9ES1MaQUYaMO0Q06HhUlak5K7VVJSs1JzS3yR_PmyX40A3T_FH-jKYQPJwKUIycHUSXrwFvoXHlmVl1w_7H_DYDaqEk</recordid><startdate>20151215</startdate><enddate>20151215</enddate><creator>Bucio-Cano, Alejandro</creator><creator>Reyes-Arellano, Alicia</creator><creator>Correa-Basurto, José</creator><creator>Bello, Martiniano</creator><creator>Torres-Jaramillo, Jenifer</creator><creator>Salgado-Zamora, Héctor</creator><creator>Curiel-Quesada, Everardo</creator><creator>Peralta-Cruz, Javier</creator><creator>Avila-Sorrosa, Alcives</creator><general>Elsevier Ltd</general><scope>6I.</scope><scope>AAFTH</scope><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></search><sort><creationdate>20151215</creationdate><title>Targeting quorum sensing by designing azoline derivatives to inhibit the N-hexanoyl homoserine lactone-receptor CviR: Synthesis as well as biological and theoretical evaluations</title><author>Bucio-Cano, Alejandro ; Reyes-Arellano, Alicia ; Correa-Basurto, José ; Bello, Martiniano ; Torres-Jaramillo, Jenifer ; Salgado-Zamora, Héctor ; Curiel-Quesada, Everardo ; Peralta-Cruz, Javier ; Avila-Sorrosa, Alcives</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c396t-1d3598326b410ea992bb2798ee297a09884ae2ad4241ad605b4e643fa227e69e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>4-Butyrolactone - analogs & derivatives</topic><topic>4-Butyrolactone - chemistry</topic><topic>4-Butyrolactone - pharmacology</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Azolines</topic><topic>Bacterial Proteins - antagonists & inhibitors</topic><topic>Bacterial Proteins - metabolism</topic><topic>Chromobacterium - drug effects</topic><topic>Chromobacterium - physiology</topic><topic>Chromobacterium violaceum</topic><topic>Cinoxacin - chemistry</topic><topic>Cinoxacin - pharmacology</topic><topic>Molecular dynamic simulation</topic><topic>Molecular Dynamics Simulation</topic><topic>Non classical bioisosteres</topic><topic>Quorum sensing</topic><topic>Quorum Sensing - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bucio-Cano, Alejandro</creatorcontrib><creatorcontrib>Reyes-Arellano, Alicia</creatorcontrib><creatorcontrib>Correa-Basurto, José</creatorcontrib><creatorcontrib>Bello, Martiniano</creatorcontrib><creatorcontrib>Torres-Jaramillo, Jenifer</creatorcontrib><creatorcontrib>Salgado-Zamora, Héctor</creatorcontrib><creatorcontrib>Curiel-Quesada, Everardo</creatorcontrib><creatorcontrib>Peralta-Cruz, Javier</creatorcontrib><creatorcontrib>Avila-Sorrosa, Alcives</creatorcontrib><collection>ScienceDirect Open Access Titles</collection><collection>Elsevier:ScienceDirect:Open Access</collection><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><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bucio-Cano, Alejandro</au><au>Reyes-Arellano, Alicia</au><au>Correa-Basurto, José</au><au>Bello, Martiniano</au><au>Torres-Jaramillo, Jenifer</au><au>Salgado-Zamora, Héctor</au><au>Curiel-Quesada, Everardo</au><au>Peralta-Cruz, Javier</au><au>Avila-Sorrosa, Alcives</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Targeting quorum sensing by designing azoline derivatives to inhibit the N-hexanoyl homoserine lactone-receptor CviR: Synthesis as well as biological and theoretical evaluations</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2015-12-15</date><risdate>2015</risdate><volume>23</volume><issue>24</issue><spage>7565</spage><epage>7577</epage><pages>7565-7577</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>[Display omitted]
To counteract bacterial resistance, we investigated the interruption of quorum sensing mediated by non-classical bioisosteres of the N-hexanoyl homoserine lactone with an azoline core. For this purpose, a set of selected 2-substituted azolines was synthesized, establishing the basis for a new protocol to synthesize 2-amino imidazolines. The synthesized compounds were evaluated as inhibitors of violacein production in Chromobacterium violaceum. Theoretical studies on bioisostere–protein interactions were performed using CviR. The results show that some azolines decreased violacein production, suggesting an antiquorum sensing profile against Gram-negative bacteria. Docking and molecular dynamic simulations together with binding free energy calculations revealed the exact binding and inhibitory profiles. These theoretical results show relationship with the in vitro activity of the azoline series.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>26654469</pmid><doi>10.1016/j.bmc.2015.10.046</doi><tpages>13</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | 4-Butyrolactone - analogs & derivatives 4-Butyrolactone - chemistry 4-Butyrolactone - pharmacology Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Azolines Bacterial Proteins - antagonists & inhibitors Bacterial Proteins - metabolism Chromobacterium - drug effects Chromobacterium - physiology Chromobacterium violaceum Cinoxacin - chemistry Cinoxacin - pharmacology Molecular dynamic simulation Molecular Dynamics Simulation Non classical bioisosteres Quorum sensing Quorum Sensing - drug effects |
| title | Targeting quorum sensing by designing azoline derivatives to inhibit the N-hexanoyl homoserine lactone-receptor CviR: Synthesis as well as biological and theoretical evaluations |
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