NDLI: A novel halogen bond and a better-known hydrogen bond cooperation of neonicotinoid and insect nicotinic acetylcholine receptor recognition

Content Provider	Springer Nature Link
Author	Duan, Hongxia Zhang, Weiwei Zhao, Jin Liang, Desheng Yang, Xinling Jin, Shuhui
Copyright Year	2012
Abstract	Neonicotinoid insecticides target the insect nicotinic acetylcholine receptor (nAChR) and are highly effective against the piercing-sucking pests. To explore the molecular interaction mechanism between the neonicotinoids and the insect nAChR, some key neonicotinoid compounds were docked into Aplysia californica acetylcholine binding protein (Ac-AChBP), which serves as a suitable structural surrogate of the insect nAChR. The binding mode study showed that the hydrogen bond force between the electronegative pharmacophore of the neonicotinoids and Cys190NH of the target binding pocket is crucial to the high efficiency of the neonicotinoids. Increasing the coplanarity between the guanidine or amidine and the electronegative pharmacophore of the neonicotinoids could increase the Π-Π stacking effect with Tyr188 of the Ac-AChBP and thus enhance the insecticidal potency. The introduction of an azide group to the chloropyridine ring of the neonicotinoids would reduce its binding ability due to the disappearance of a novel halogen bonding interaction. A series of novel neonicotinoid molecules were designed based on the halogen bonding interaction and two compounds with 6-bromopyridine-3-yl and 6-(trifluoromethyl)-3-pyridinyl were found to be with potential insecticidal activities. Figure A new binding model between the neonicotinoids and the insect target nAChR with the hydrogen bond force, the π-π stacking effect and the halogen bond interaction is successfully generated by the Surflex-Dock algorithm. Two compounds with 6-bromopyridine-3-yl and 6-(trifluoromethyl)-3-pyridinyl are found to be good neonicotinoids candidates with potentially high activities
Starting Page	3867
Ending Page	3875
Page Count	9
File Format	PDF
ISSN	16102940
Journal	Journal of Molecular Modeling
Volume Number	18
Issue Number	8
e-ISSN	09485023
Language	English
Publisher	Springer-Verlag
Publisher Date	2012-03-17
Publisher Place	Berlin, Heidelberg
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Halogen bonding Hydrogen bond Neonicotinoid Nicotinic acetylcholine receptor Π–Π stacking Computer Application in Life Sciences Biomedicine general Life Sciences Molecular Medicine Computer Applications in Chemistry Health Informatics
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Physical and Theoretical Chemistry Computational Theory and Mathematics Catalysis Inorganic Chemistry Computer Science Applications

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