文献类型：期刊文献

中文题名：Water bridges are essential to neonicotinoids: Insights from synthesis,bioassay and molecular modelling studies

英文题名：Water bridges are essential to neonicotinoids: Insights from synthesis,bioassay and molecular modelling studies

作者：Chengchun Zhu[1];Guanglong Li[1];Keya Xiao[1];Xusheng Shao[1];Jiagao Cheng[1];Zhong Li[1,2]

机构：[1]Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology;[2]Shanghai Collaborative Innovation Center for Biomanufacturing Technology

年份：2019

卷号：30

期号：1

起止页码：255

中文期刊名：Chinese Chemical Letters

外文期刊名：中国化学快报（英文版）

收录：CSTPCD;;Scopus;CSCD:【CSCD2019_2020】；PubMed;

基金：the financial supports from the National Natural Science Foundation of China (Nos. 21572059, 21172070);Innovation Program of Shanghai Municipal Education Commission (No. 201701070002E00037)

语种：英文

中文关键词：Neonicotinoids;Water;bridge;Insecticidal;activity;Cyano;group;Molecular;design

外文关键词：Neonicotinoids;Water bridge;Insecticidal activity;Cyano group;Molecular design

摘要：Water-bridged H-bonds have been observed in many cases of ligand-receptor recognitions. To explore the roles of water bridges in the binding of neonicotinoids with receptors, twenty-four neonicotinoid compounds with nine fragments, including 1 H-1,2,3-triazole, CN, COOMe, CONHNH_2, CONHMe, NO_2,NH_2, NHCOMe and NHCSNH_2 were synthesized and evaluated, of which, compounds with cyano group showed the best activities against Aphis craccivora. Accordingly, the cyano group is the optimal fragment mimicking the water bridge. Two cyano-substituted cis-nitromethylene compounds display good insecticidal activities, whereas the LC_(50) values are lower than those of their corresponding prototypes.Docking study showed that the cyano group acts only as H-bond acceptor, while the water bridge can act as both donor and acceptor. It revealed that the water bridge might be stable in the active site and was not suitable to be replaced by other groups. The findings illustrated that the water bridge is necessary for high insecticidal activities of neonicotinoids, which should be also helpful in better understanding the binding mode of neonicotinoids.
Water-bridged H-bonds have been observed in many cases of ligand-receptor recognitions. To explore the roles of water bridges in the binding of neonicotinoids with receptors, twenty-four neonicotinoid compounds with nine fragments, including 1 H-1,2,3-triazole, CN, COOMe, CONHNH_2, CONHMe, NO_2,NH_2, NHCOMe and NHCSNH_2 were synthesized and evaluated, of which, compounds with cyano group showed the best activities against Aphis craccivora. Accordingly, the cyano group is the optimal fragment mimicking the water bridge. Two cyano-substituted cis-nitromethylene compounds display good insecticidal activities, whereas the LC_(50) values are lower than those of their corresponding prototypes.Docking study showed that the cyano group acts only as H-bond acceptor, while the water bridge can act as both donor and acceptor. It revealed that the water bridge might be stable in the active site and was not suitable to be replaced by other groups. The findings illustrated that the water bridge is necessary for high insecticidal activities of neonicotinoids, which should be also helpful in better understanding the binding mode of neonicotinoids.