Design, synthesis, and evaluation of novel 2-phenylpropionic acid derivatives as dual COX inhibitory-antibacterial agents
A series of 2-(4-substitutedmethylphenyl)propionic acid derivatives (6a-6m) were synthesized, characterized and evaluated for cyclooxygenase (COX) enzyme inhibitory and antimicrobial activity. Test compounds that exhibited good COX inhibition and antibacterial activity were further screened for thei...
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| Veröffentlicht in: | Journal of enzyme inhibition and medicinal chemistry 2017-01, Vol.32 (1), p.732-745 |
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| container_title | Journal of enzyme inhibition and medicinal chemistry |
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| creator | Karaca Gençer, Hülya Acar Çevik, Ulviye Kaya Çavuşoğlu, Betül Sağlık, Begüm Nurpelin Levent, Serkan Atlı, Özlem Ilgın, Sinem Özkay, Yusuf Kaplancıklı, Zafer Asım |
| description | A series of 2-(4-substitutedmethylphenyl)propionic acid derivatives (6a-6m) were synthesized, characterized and evaluated for cyclooxygenase (COX) enzyme inhibitory and antimicrobial activity. Test compounds that exhibited good COX inhibition and antibacterial activity were further screened for their cytotoxicity and genotoxicity. Compounds 6h and 6l showed better COX-1 and COX-2 inhibition when compared to ibuprofen. Inhibition potency of these compounds against COX-2 was very close to that of nimesulide. The compounds 6d, 6h, 6l and 6m displayed promising antibacterial property when compared to chloramphenicol. However, the compound 6l was emerged as the best dual COX inhibitory-antibacterial agent in this study. The ADME prediction of the compounds revealed that they may have a good pharmacokinetic profile. Docking results of the compounds 6h and 6l with COX-1 (PDB ID: 1EQG) also exhibited a strong binding profile. |
| doi_str_mv | 10.1080/14756366.2017.1310726 |
| format | Article |
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Test compounds that exhibited good COX inhibition and antibacterial activity were further screened for their cytotoxicity and genotoxicity. Compounds 6h and 6l showed better COX-1 and COX-2 inhibition when compared to ibuprofen. Inhibition potency of these compounds against COX-2 was very close to that of nimesulide. The compounds 6d, 6h, 6l and 6m displayed promising antibacterial property when compared to chloramphenicol. However, the compound 6l was emerged as the best dual COX inhibitory-antibacterial agent in this study. The ADME prediction of the compounds revealed that they may have a good pharmacokinetic profile. Docking results of the compounds 6h and 6l with COX-1 (PDB ID: 1EQG) also exhibited a strong binding profile.</description><identifier>ISSN: 1475-6366</identifier><identifier>EISSN: 1475-6374</identifier><identifier>DOI: 10.1080/14756366.2017.1310726</identifier><identifier>PMID: 28413890</identifier><language>eng</language><publisher>England: Taylor & Francis</publisher><subject>Acids ; antibacterial ; Antibacterial activity ; Antibacterial agents ; Antimicrobial activity ; Antimicrobial agents ; Chloramphenicol ; COX inhibition ; Cyclooxygenase-1 ; Cyclooxygenase-2 ; Cytotoxicity ; docking ; Drug resistance ; dual effect ; Enzymes ; Genotoxicity ; Ibuprofen ; Inflammatory diseases ; International organizations ; Laboratories ; Methods ; Nimesulide ; Nonsteroidal anti-inflammatory drugs ; Patients ; Pharmaceutical sciences ; Pharmacy ; Phenylpropionic acid ; Propionic acid</subject><ispartof>Journal of enzyme inhibition and medicinal chemistry, 2017-01, Vol.32 (1), p.732-745</ispartof><rights>2017 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group. 2017</rights><rights>2017 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group. This work is licensed under the Creative Commons Attribution License http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2017 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group. 2017 The Author(s).</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c562t-cb08354bec2e85863f8c14ece350e986cbc694f7e2b8ea6245ec6e045feec4ce3</citedby><cites>FETCH-LOGICAL-c562t-cb08354bec2e85863f8c14ece350e986cbc694f7e2b8ea6245ec6e045feec4ce3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC6445163/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC6445163/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,864,885,2102,27502,27924,27925,53791,53793,59143,59144</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28413890$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Karaca Gençer, Hülya</creatorcontrib><creatorcontrib>Acar Çevik, Ulviye</creatorcontrib><creatorcontrib>Kaya Çavuşoğlu, Betül</creatorcontrib><creatorcontrib>Sağlık, Begüm Nurpelin</creatorcontrib><creatorcontrib>Levent, Serkan</creatorcontrib><creatorcontrib>Atlı, Özlem</creatorcontrib><creatorcontrib>Ilgın, Sinem</creatorcontrib><creatorcontrib>Özkay, Yusuf</creatorcontrib><creatorcontrib>Kaplancıklı, Zafer Asım</creatorcontrib><title>Design, synthesis, and evaluation of novel 2-phenylpropionic acid derivatives as dual COX inhibitory-antibacterial agents</title><title>Journal of enzyme inhibition and medicinal chemistry</title><addtitle>J Enzyme Inhib Med Chem</addtitle><description>A series of 2-(4-substitutedmethylphenyl)propionic acid derivatives (6a-6m) were synthesized, characterized and evaluated for cyclooxygenase (COX) enzyme inhibitory and antimicrobial activity. Test compounds that exhibited good COX inhibition and antibacterial activity were further screened for their cytotoxicity and genotoxicity. Compounds 6h and 6l showed better COX-1 and COX-2 inhibition when compared to ibuprofen. Inhibition potency of these compounds against COX-2 was very close to that of nimesulide. The compounds 6d, 6h, 6l and 6m displayed promising antibacterial property when compared to chloramphenicol. However, the compound 6l was emerged as the best dual COX inhibitory-antibacterial agent in this study. The ADME prediction of the compounds revealed that they may have a good pharmacokinetic profile. Docking results of the compounds 6h and 6l with COX-1 (PDB ID: 1EQG) also exhibited a strong binding profile.</description><subject>Acids</subject><subject>antibacterial</subject><subject>Antibacterial activity</subject><subject>Antibacterial agents</subject><subject>Antimicrobial activity</subject><subject>Antimicrobial agents</subject><subject>Chloramphenicol</subject><subject>COX inhibition</subject><subject>Cyclooxygenase-1</subject><subject>Cyclooxygenase-2</subject><subject>Cytotoxicity</subject><subject>docking</subject><subject>Drug resistance</subject><subject>dual effect</subject><subject>Enzymes</subject><subject>Genotoxicity</subject><subject>Ibuprofen</subject><subject>Inflammatory diseases</subject><subject>International organizations</subject><subject>Laboratories</subject><subject>Methods</subject><subject>Nimesulide</subject><subject>Nonsteroidal anti-inflammatory drugs</subject><subject>Patients</subject><subject>Pharmaceutical sciences</subject><subject>Pharmacy</subject><subject>Phenylpropionic acid</subject><subject>Propionic acid</subject><issn>1475-6366</issn><issn>1475-6374</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>0YH</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>DOA</sourceid><recordid>eNp9kU2P0zAQhiMEYpeFnwCyxHVT_BXHuSBW5WullfYCEjdr4kxaV6ld7KQo_x53263YCyePZp55X4_eonjL6IJRTT8wWVdKKLXglNULJhituXpWXB76pRK1fH6ulbooXqW0oZQzzuTL4oJryYRu6GUxf8bkVv6apNmP61ynawK-I7iHYYLRBU9CT3zY40B4uVujn4ddDLs8cJaAdR3pMLp9RveYCCTSTTCQ5f0v4vzatW4McS7Bj64FO2YyD2GFfkyvixc9DAnfnN6r4ufXLz-W38u7-2-3y5u70laKj6VtqRaVbNFy1JVWoteWSbQoKoqNVra1qpF9jbzVCIrLCq1CKqse0cqMXRW3R90uwMbsottCnE0AZx4aIa4MxNHZAU1bY09BZaHOSi6lBsxmmgusBcW2yVofj1q7qd1mKN8RYXgi-nTi3dqswt4oKSumRBZ4fxKI4feEaTSbMEWf7zecNRUXvHmgqiNlY0gpYn92YNQc0jeP6ZtD-uaUft579-_3zluPcWfg0xFwvg9xC39CHDozwjyE2Efw1iUj_u_xF77twjA</recordid><startdate>20170101</startdate><enddate>20170101</enddate><creator>Karaca Gençer, Hülya</creator><creator>Acar Çevik, Ulviye</creator><creator>Kaya Çavuşoğlu, Betül</creator><creator>Sağlık, Begüm Nurpelin</creator><creator>Levent, Serkan</creator><creator>Atlı, Özlem</creator><creator>Ilgın, Sinem</creator><creator>Özkay, Yusuf</creator><creator>Kaplancıklı, Zafer Asım</creator><general>Taylor & Francis</general><general>Taylor & Francis Ltd</general><general>Taylor & Francis Group</general><scope>0YH</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7T5</scope><scope>7X7</scope><scope>7XB</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>H94</scope><scope>K9.</scope><scope>M0S</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>5PM</scope><scope>DOA</scope></search><sort><creationdate>20170101</creationdate><title>Design, synthesis, and evaluation of novel 2-phenylpropionic acid derivatives as dual COX inhibitory-antibacterial agents</title><author>Karaca Gençer, Hülya ; Acar Çevik, Ulviye ; Kaya Çavuşoğlu, Betül ; Sağlık, Begüm Nurpelin ; Levent, Serkan ; Atlı, Özlem ; Ilgın, Sinem ; Özkay, Yusuf ; Kaplancıklı, Zafer Asım</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c562t-cb08354bec2e85863f8c14ece350e986cbc694f7e2b8ea6245ec6e045feec4ce3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Acids</topic><topic>antibacterial</topic><topic>Antibacterial activity</topic><topic>Antibacterial agents</topic><topic>Antimicrobial activity</topic><topic>Antimicrobial agents</topic><topic>Chloramphenicol</topic><topic>COX inhibition</topic><topic>Cyclooxygenase-1</topic><topic>Cyclooxygenase-2</topic><topic>Cytotoxicity</topic><topic>docking</topic><topic>Drug resistance</topic><topic>dual effect</topic><topic>Enzymes</topic><topic>Genotoxicity</topic><topic>Ibuprofen</topic><topic>Inflammatory diseases</topic><topic>International organizations</topic><topic>Laboratories</topic><topic>Methods</topic><topic>Nimesulide</topic><topic>Nonsteroidal anti-inflammatory drugs</topic><topic>Patients</topic><topic>Pharmaceutical sciences</topic><topic>Pharmacy</topic><topic>Phenylpropionic acid</topic><topic>Propionic acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Karaca Gençer, Hülya</creatorcontrib><creatorcontrib>Acar Çevik, Ulviye</creatorcontrib><creatorcontrib>Kaya Çavuşoğlu, Betül</creatorcontrib><creatorcontrib>Sağlık, Begüm Nurpelin</creatorcontrib><creatorcontrib>Levent, Serkan</creatorcontrib><creatorcontrib>Atlı, Özlem</creatorcontrib><creatorcontrib>Ilgın, Sinem</creatorcontrib><creatorcontrib>Özkay, Yusuf</creatorcontrib><creatorcontrib>Kaplancıklı, Zafer Asım</creatorcontrib><collection>Access via Taylor & Francis (Open Access Collection)</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Immunology Abstracts</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Journal of enzyme inhibition and medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Karaca Gençer, Hülya</au><au>Acar Çevik, Ulviye</au><au>Kaya Çavuşoğlu, Betül</au><au>Sağlık, Begüm Nurpelin</au><au>Levent, Serkan</au><au>Atlı, Özlem</au><au>Ilgın, Sinem</au><au>Özkay, Yusuf</au><au>Kaplancıklı, Zafer Asım</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, synthesis, and evaluation of novel 2-phenylpropionic acid derivatives as dual COX inhibitory-antibacterial agents</atitle><jtitle>Journal of enzyme inhibition and medicinal chemistry</jtitle><addtitle>J Enzyme Inhib Med Chem</addtitle><date>2017-01-01</date><risdate>2017</risdate><volume>32</volume><issue>1</issue><spage>732</spage><epage>745</epage><pages>732-745</pages><issn>1475-6366</issn><eissn>1475-6374</eissn><abstract>A series of 2-(4-substitutedmethylphenyl)propionic acid derivatives (6a-6m) were synthesized, characterized and evaluated for cyclooxygenase (COX) enzyme inhibitory and antimicrobial activity. Test compounds that exhibited good COX inhibition and antibacterial activity were further screened for their cytotoxicity and genotoxicity. Compounds 6h and 6l showed better COX-1 and COX-2 inhibition when compared to ibuprofen. Inhibition potency of these compounds against COX-2 was very close to that of nimesulide. The compounds 6d, 6h, 6l and 6m displayed promising antibacterial property when compared to chloramphenicol. However, the compound 6l was emerged as the best dual COX inhibitory-antibacterial agent in this study. The ADME prediction of the compounds revealed that they may have a good pharmacokinetic profile. Docking results of the compounds 6h and 6l with COX-1 (PDB ID: 1EQG) also exhibited a strong binding profile.</abstract><cop>England</cop><pub>Taylor & Francis</pub><pmid>28413890</pmid><doi>10.1080/14756366.2017.1310726</doi><tpages>14</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Acids antibacterial Antibacterial activity Antibacterial agents Antimicrobial activity Antimicrobial agents Chloramphenicol COX inhibition Cyclooxygenase-1 Cyclooxygenase-2 Cytotoxicity docking Drug resistance dual effect Enzymes Genotoxicity Ibuprofen Inflammatory diseases International organizations Laboratories Methods Nimesulide Nonsteroidal anti-inflammatory drugs Patients Pharmaceutical sciences Pharmacy Phenylpropionic acid Propionic acid |
| title | Design, synthesis, and evaluation of novel 2-phenylpropionic acid derivatives as dual COX inhibitory-antibacterial agents |
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