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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Published in | Proceedings of the National Academy of Sciences - PNAS Vol. 105; no. 21; pp. 7359 - 7364 |
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Main Authors | , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
United States
National Academy of Sciences
27.05.2008
National Acad Sciences |
Subjects | |
Online Access | Get full text |
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Summary: | 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. |
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Bibliography: | http://dx.doi.org/10.1073/pnas.0800571105 http://hdl.handle.net/10113/15990 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 Author contributions: A.R.K., S.S., D.D., U.R.B., G.G.C., and K.J.L. designed research; Z.W., M.T., N.G.A., U.R.B., G.G.C., and K.J.L. performed research; S.S., D.D., and C.D.H. analyzed data; and A.R.K., Z.W., S.S., M.T., C.D.H., U.R.B., G.G.C., and K.J.L. wrote the paper. Edited by Barry J. Beaty, Colorado State University, Fort Collins, CO, and approved April 1, 2008 |
ISSN: | 0027-8424 1091-6490 |
DOI: | 10.1073/pnas.0800571105 |