Synthesis and bioassay of improved mosquito repellents predicted from chemical structure
Mosquito repellency data on acylpiperidines derived from the U.S. Department of Agriculture archives were modeled by using molecular descriptors calculated by CODESSA PRO software. An artificial neural network model was developed for the correlation of these archival results and used to predict the...
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| Veröffentlicht in: | Proceedings of the National Academy of Sciences - PNAS 2008-05, Vol.105 (21), p.7359-7364 |
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| container_title | Proceedings of the National Academy of Sciences - PNAS |
| container_volume | 105 |
| creator | Katritzky, Alan R Wang, Zuoquan Slavov, Svetoslav Tsikolia, Maia Dobchev, Dimitar Akhmedov, Novruz G Hall, C. Dennis Bernier, Ulrich R Clark, Gary G Linthicum, Kenneth J |
| description | Mosquito repellency data on acylpiperidines derived from the U.S. Department of Agriculture archives were modeled by using molecular descriptors calculated by CODESSA PRO software. An artificial neural network model was developed for the correlation of these archival results and used to predict the repellent activity of novel compounds of similar structures. A series of 34 promising N-acylpiperidine mosquito repellent candidates (4a-4q') were synthesized by reactions of acylbenzotriazoles 2a-2p with piperidines 3a-3f. Compounds (4a-4q') were screened as topically applied mosquito repellents by measuring the duration of repellency after application to cloth patches worn on the arms of human volunteers. Some compounds that were evaluated repelled mosquitoes as much as three times longer than N,N-diethyl-m-toluamide (DEET), the most widely used repellent throughout the world. The newly measured durations of repellency were used to obtain a superior correlation equation relating mosquito repellency to molecular structure. |
| doi_str_mv | 10.1073/pnas.0800571105 |
| format | Article |
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Compounds (4a-4q') were screened as topically applied mosquito repellents by measuring the duration of repellency after application to cloth patches worn on the arms of human volunteers. Some compounds that were evaluated repelled mosquitoes as much as three times longer than N,N-diethyl-m-toluamide (DEET), the most widely used repellent throughout the world. The newly measured durations of repellency were used to obtain a superior correlation equation relating mosquito repellency to molecular structure.</description><identifier>ISSN: 0027-8424</identifier><identifier>EISSN: 1091-6490</identifier><identifier>DOI: 10.1073/pnas.0800571105</identifier><identifier>PMID: 18508970</identifier><language>eng</language><publisher>United States: National Academy of Sciences</publisher><subject>Aedes aegypti ; Agriculture ; Amides ; Animals ; Bioassay ; Bioassays ; Biological Assay ; Bites and stings ; Chemical compounds ; Chemical reactions ; chemical structure ; CODESSA PRO software ; computer software ; Correlation analysis ; Culicidae ; Culicidae - drug effects ; Drug Design ; insect repellents ; Insect Repellents - chemical synthesis ; Insect Repellents - chemistry ; Insect Repellents - pharmacology ; Magnetic Resonance Spectroscopy ; Modeling ; Models, Chemical ; Molecular structure ; Molecules ; Mosquitoes ; Mosquitos ; N-acylpiperidines ; Neural networks ; Neural Networks (Computer) ; Organic farming ; Physical Sciences ; Piperidines ; Piperidines - chemical synthesis ; Piperidines - chemistry ; Piperidines - pharmacology ; Quantitative Structure-Activity Relationship ; quantitative structure-activity relationships ; Receptors ; Software ; synthesis</subject><ispartof>Proceedings of the National Academy of Sciences - PNAS, 2008-05, Vol.105 (21), p.7359-7364</ispartof><rights>Copyright 2008 The National Academy of Sciences of the United States of America</rights><rights>Copyright National Academy of Sciences May 27, 2008</rights><rights>2008 by The National Academy of Sciences of the USA</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c618t-5c811dd571eb48ff8edd30f94b4e58c4e926661e597490a8da0e0af1b2da54623</citedby><cites>FETCH-LOGICAL-c618t-5c811dd571eb48ff8edd30f94b4e58c4e926661e597490a8da0e0af1b2da54623</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Uhttp://www.pnas.org/content/105/21.cover.gif</thumbnail><linktopdf>$$Uhttps://www.jstor.org/stable/pdf/25462602$$EPDF$$P50$$Gjstor$$H</linktopdf><linktohtml>$$Uhttps://www.jstor.org/stable/25462602$$EHTML$$P50$$Gjstor$$H</linktohtml><link.rule.ids>230,314,727,780,784,803,885,27924,27925,53791,53793,58017,58250</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18508970$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Katritzky, Alan R</creatorcontrib><creatorcontrib>Wang, Zuoquan</creatorcontrib><creatorcontrib>Slavov, Svetoslav</creatorcontrib><creatorcontrib>Tsikolia, Maia</creatorcontrib><creatorcontrib>Dobchev, Dimitar</creatorcontrib><creatorcontrib>Akhmedov, Novruz G</creatorcontrib><creatorcontrib>Hall, C. Dennis</creatorcontrib><creatorcontrib>Bernier, Ulrich R</creatorcontrib><creatorcontrib>Clark, Gary G</creatorcontrib><creatorcontrib>Linthicum, Kenneth J</creatorcontrib><title>Synthesis and bioassay of improved mosquito repellents predicted from chemical structure</title><title>Proceedings of the National Academy of Sciences - PNAS</title><addtitle>Proc Natl Acad Sci U S A</addtitle><description>Mosquito repellency data on acylpiperidines derived from the U.S. Department of Agriculture archives were modeled by using molecular descriptors calculated by CODESSA PRO software. An artificial neural network model was developed for the correlation of these archival results and used to predict the repellent activity of novel compounds of similar structures. A series of 34 promising N-acylpiperidine mosquito repellent candidates (4a-4q') were synthesized by reactions of acylbenzotriazoles 2a-2p with piperidines 3a-3f. Compounds (4a-4q') were screened as topically applied mosquito repellents by measuring the duration of repellency after application to cloth patches worn on the arms of human volunteers. Some compounds that were evaluated repelled mosquitoes as much as three times longer than N,N-diethyl-m-toluamide (DEET), the most widely used repellent throughout the world. The newly measured durations of repellency were used to obtain a superior correlation equation relating mosquito repellency to molecular structure.</description><subject>Aedes aegypti</subject><subject>Agriculture</subject><subject>Amides</subject><subject>Animals</subject><subject>Bioassay</subject><subject>Bioassays</subject><subject>Biological Assay</subject><subject>Bites and stings</subject><subject>Chemical compounds</subject><subject>Chemical reactions</subject><subject>chemical structure</subject><subject>CODESSA PRO software</subject><subject>computer software</subject><subject>Correlation analysis</subject><subject>Culicidae</subject><subject>Culicidae - drug effects</subject><subject>Drug Design</subject><subject>insect repellents</subject><subject>Insect Repellents - chemical synthesis</subject><subject>Insect Repellents - chemistry</subject><subject>Insect Repellents - pharmacology</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Modeling</subject><subject>Models, Chemical</subject><subject>Molecular structure</subject><subject>Molecules</subject><subject>Mosquitoes</subject><subject>Mosquitos</subject><subject>N-acylpiperidines</subject><subject>Neural networks</subject><subject>Neural Networks (Computer)</subject><subject>Organic farming</subject><subject>Physical Sciences</subject><subject>Piperidines</subject><subject>Piperidines - chemical synthesis</subject><subject>Piperidines - chemistry</subject><subject>Piperidines - pharmacology</subject><subject>Quantitative Structure-Activity Relationship</subject><subject>quantitative structure-activity relationships</subject><subject>Receptors</subject><subject>Software</subject><subject>synthesis</subject><issn>0027-8424</issn><issn>1091-6490</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9ks1v1DAQxS0EotvCmRMQ9YC4bDt2bMe-IKGKL6kSh1KJm-XYTterJE5tp2L_exztqgscOPkwv3meN28QeoXhAkNTX06jThcgAFiDMbAnaIVB4jWnEp6iFQBp1oISeoJOU9oCgGQCnqMTLBgI2cAK_bzZjXnjkk-VHm3V-qBT0rsqdJUfphgenK2GkO5nn0MV3eT63o05VVN01ptcql0MQ2U2bvBG91XKcTZ5ju4FetbpPrmXh_cM3X7-9OPq6_r6-5dvVx-v14ZjkdfMCIytLeO7loquE87aGjpJW-qYMNRJwjnHjsmmeNLCanCgO9wSqxnlpD5DH_a609wOzpoyXdS9mqIfdNypoL36uzL6jboLD4rUkje4KQLvDgIx3M8uZTX4ZIpPPbowJ0XKQikTy0_n_4DbMMexmCsMrrHkwAt0uYdMDClF1z1OgkEtkaklMnWMrHS8-dPAkT9kVID3B2DpPMoxRbBqaiZVN_d9dr9yQd_-Hy3E6z2xTTnER4Qsu-RAjgqdDkrfRZ_U7c1ir9wOAMVQ_waRL79s</recordid><startdate>20080527</startdate><enddate>20080527</enddate><creator>Katritzky, Alan R</creator><creator>Wang, Zuoquan</creator><creator>Slavov, Svetoslav</creator><creator>Tsikolia, Maia</creator><creator>Dobchev, Dimitar</creator><creator>Akhmedov, Novruz G</creator><creator>Hall, C. 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Dennis</au><au>Bernier, Ulrich R</au><au>Clark, Gary G</au><au>Linthicum, Kenneth J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and bioassay of improved mosquito repellents predicted from chemical structure</atitle><jtitle>Proceedings of the National Academy of Sciences - PNAS</jtitle><addtitle>Proc Natl Acad Sci U S A</addtitle><date>2008-05-27</date><risdate>2008</risdate><volume>105</volume><issue>21</issue><spage>7359</spage><epage>7364</epage><pages>7359-7364</pages><issn>0027-8424</issn><eissn>1091-6490</eissn><abstract>Mosquito repellency data on acylpiperidines derived from the U.S. Department of Agriculture archives were modeled by using molecular descriptors calculated by CODESSA PRO software. An artificial neural network model was developed for the correlation of these archival results and used to predict the repellent activity of novel compounds of similar structures. A series of 34 promising N-acylpiperidine mosquito repellent candidates (4a-4q') were synthesized by reactions of acylbenzotriazoles 2a-2p with piperidines 3a-3f. Compounds (4a-4q') were screened as topically applied mosquito repellents by measuring the duration of repellency after application to cloth patches worn on the arms of human volunteers. Some compounds that were evaluated repelled mosquitoes as much as three times longer than N,N-diethyl-m-toluamide (DEET), the most widely used repellent throughout the world. The newly measured durations of repellency were used to obtain a superior correlation equation relating mosquito repellency to molecular structure.</abstract><cop>United States</cop><pub>National Academy of Sciences</pub><pmid>18508970</pmid><doi>10.1073/pnas.0800571105</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Aedes aegypti Agriculture Amides Animals Bioassay Bioassays Biological Assay Bites and stings Chemical compounds Chemical reactions chemical structure CODESSA PRO software computer software Correlation analysis Culicidae Culicidae - drug effects Drug Design insect repellents Insect Repellents - chemical synthesis Insect Repellents - chemistry Insect Repellents - pharmacology Magnetic Resonance Spectroscopy Modeling Models, Chemical Molecular structure Molecules Mosquitoes Mosquitos N-acylpiperidines Neural networks Neural Networks (Computer) Organic farming Physical Sciences Piperidines Piperidines - chemical synthesis Piperidines - chemistry Piperidines - pharmacology Quantitative Structure-Activity Relationship quantitative structure-activity relationships Receptors Software synthesis |
| title | Synthesis and bioassay of improved mosquito repellents predicted from chemical structure |
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