Citation: Zhu Chengchun, Li Guanglong, Xiao Keya, Shao Xusheng, Cheng Jiagao, Li Zhong. Water bridges are essential to neonicotinoids: Insights from synthesis, bioassay and molecular modelling studies[J]. Chinese Chemical Letters, ;2019, 30(1): 255-258. doi: 10.1016/j.cclet.2018.05.013 shu

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

Zhu Chengchun ^a,1 ,
Li Guanglong ^a,1 ,
Xiao Keya ^a ,
Shao Xusheng ^a ,
Cheng Jiagao ^a,, ,
Li Zhong ^a,b

a.
Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
b.
Shanghai Collaborative Innovation Center for Biomanufacturing Technology, Shanghai 200237, China

Corresponding author: Cheng Jiagao, jgcheng@ecust.edu.cn

Received Date: 6 April 2018
Revised Date: 3 May 2018
Accepted Date: 4 May 2018
Available Online: 7 January 2018

Figures(4)

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 1H-1, 2, 3-triazole, CN, COOMe, CONHNH₂, CONHMe, NO₂, NH₂, NHCOMe and NHCSNH₂ 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 LC50 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.
- Neonicotinoids,
- Water bridge,
- Insecticidal activity,
- Cyano group,
- Molecular design
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