PMID: 11312774Apr 21, 2001Paper

Neonicotinoid insecticides: molecular features conferring selectivity for insect versus mammalian nicotinic receptors

Journal of Agricultural and Food Chemistry
M TomizawaJ E Casida

Abstract

The favorable selective toxicity of neonicotinoid insecticides (represented here by imidacloprid, thiacloprid, and a nitromethylene analogue) for insects versus mammals is not shared by three of their N-unsubstituted imine derivatives or by nicotine or epibatidine. The same selectivity pattern is evident at the receptor level, i.e., the insect nicotinic acetylcholine receptor (nAChR) versus mammalian nAChR subtypes (alpha1, alpha3, alpha4, and alpha7) assayed independently. The insect-selective compounds are not protonated with a nitroimine, cyanoimine, or nitromethylene group and the mammalian-selective compounds are ionized at physiological pH. We propose that the negatively charged tip of the nitro or cyano group (not a partial positive charge at imidazolidine N-1 as suggested earlier) interacts with a putative cationic subsite of the insect nAChR. This contrasts with the mammalian nAChRs where the iminium cation (+C-NH2 <--> C =+NH2) of the neonicotinoid imine derivatives or ammonium nitrogen of nicotine or epibatidine interacts with the anionic subsite.

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Citations

Aug 2, 2013·Archives of Environmental Contamination and Toxicology·Valentina ColomboVincent J Pettigrove
Jan 12, 2007·Invertebrate Neuroscience : in·Neil S Millar, Ian Denholm
Sep 17, 2013·Cell Biology and Toxicology·Timothy C Marrs, R L Maynard
Jan 20, 2004·Toxicology and Applied Pharmacology·Jean-Luc BrunetLuc P Belzunces
Mar 24, 2004·Trends in Genetics : TIG·Richard H Ffrench-ConstantGaelle Le Goff
Nov 8, 2001·Trends in Pharmacological Sciences·K MatsudaD B Sattelle
May 22, 2002·Insect Biochemistry and Molecular Biology·I SultanaY Ozoe
Feb 24, 2011·Journal of Agricultural and Food Chemistry·Motohiro Tomizawa, John E Casida
Aug 25, 2010·Journal of Agricultural and Food Chemistry·John E Casida
Sep 30, 2010·Journal of Agricultural and Food Chemistry·Motohiro TomizawaJohn E Casida
Jul 31, 2013·Journal of Agricultural and Food Chemistry·Xusheng ShaoJohn E Casida
Jan 31, 2008·Proceedings of the National Academy of Sciences of the United States of America·Motohiro TomizawaJohn E Casida
Mar 1, 2013·Food Additives & Contaminants. Part B, Surveillance·Leonardo SabatinoGiacomo Gagliano
Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online·Chuan-Wen SunDing-Rong Yang
Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online·Chuan-Wen SunHong-Fei Bu
Nov 9, 2011·Acta Crystallographica. Section E, Structure Reports Online·Jian Wu
Jan 16, 2013·Annual Review of Entomology·John E Casida, Kathleen A Durkin
Sep 5, 2002·Annual Review of Entomology·Motohiro Tomizawa, John E Casida
Apr 12, 2005·Annual Review of Pharmacology and Toxicology·Motohiro Tomizawa, John E Casida
May 9, 2007·Proceedings of the National Academy of Sciences of the United States of America·Motohiro TomizawaJohn E Casida
Aug 13, 2013·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·Predrag KalajdzicCharalambos Savakis
Oct 30, 2015·Critical Reviews in Toxicology·Larry P SheetsRichard C Peffer
Aug 21, 2008·Pest Management Science·Peter Jeschke, Ralf Nauen
Mar 17, 2009·Biochemical and Biophysical Research Communications·Gunjan PandeyJohn G Oakeshott

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