Actions between neonicotinoids and key residues of insect nAChR based on an ab initio quantum chemistry study: Hydrogen bonding and cooperative π-π interaction
Neonicotinoid insecticides show selective actions on insect nicotinic acetylcholine receptor (nAChR). Two key residues (Trp and Arg/Lys) have been identified as contributing to the neonicotinoid binding. To investigate the selective mechanism, a computational model was set up to simulate the interaction between residues (Trp and Arg) of insect nAChR and neonicotinoids by quantum chemistry method. Three analogues of neonicotinoids derivatives without the chloropyridinyl moiety and 3-methylindole (3MI), guanidinium (Gua) were used to mimic the neonicotinoids and the sidechain of key residues Trp and Arg accordingly. Interaction features of 3MI-analogues, analogues-Gua and 3MI-analogues-Gua complexes were analyzed comparatively. Hydrogen bonding between the nitro group of analogues and Gua was found to be the most important for binding. Moreover, the cooperative π-π interaction between analogues and the indole ring, which is strengthened by the existence of Gua, also contributes to the binding. The alternative binding model of neonicotinoids proposed here, although slightly different from others, might be close to the actual.
Neonicotinoids Nicotinic acetylcholine receptor Binding model
Yanli Wang Jiagao Cheng Xuhong Qian Zhong Li
Shanghai Key Lab. of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
国际会议
杭州
英文
826-840
2007-04-01（万方平台首次上网日期，不代表论文的发表时间）