Citation: Yang Huibin, Qi Huitang, Liu Tian, Shao Xusheng, Yang Qing, Qian Xuhong. Naphthalimide and quinoline derivatives as inhibitors for insect N-acetyl-β-D-hexosaminidase[J]. Chinese Chemical Letters, ;2019, 30(5): 977-980. doi: 10.1016/j.cclet.2019.01.023 shu

Naphthalimide and quinoline derivatives as inhibitors for insect N-acetyl-β-D-hexosaminidase

Yang Huibin ^a,b,1 ,
Qi Huitang ^c,1 ,
Liu Tian ^c ,
Shao Xusheng ^a ,
Yang Qing ^c,*, ,
Qian Xuhong ^a,*,

a.
Shanghai Key Laboratory of Chemical Biology, Institute of Pesticides and Pharmaceuticals, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
b.
State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Sinochem Agrochemicals Research and Development Co., Ltd., Shenyang 110021, China
c.
School of Life Science and Biotechnology, Dalian University of Technology, Dalian 116024, China

E-mail addresses:

Received Date: 19 December 2018
Revised Date: 22 January 2019
Accepted Date: 22 January 2019
Available Online: 23 May 2019

Figures(4)

Insect chitinolytic β-N-acetyl-D-hexosaminidase, such as OfHex1 from Ostrinia furnacalis, is a potential target for insecticide design. Among the known OfHex1 inhibitors, Q2 is of great interest because it is the first non-carbohydrate inhibitor. In this study, we designed and synthesized a series of Q2 derivatives by replacing the thiadiazole and naphthalimide groups and changing the linker length. Compound 3m showed the best inhibitory activity with a K_i value of 0.34 μmol/L against OfHex1, which is about onequarter that of Q2 (K_i=1.4 μmol/L). Compound 6a showed the best inhibitory activity among the quinoline-containing derivatives (K_i=2.3 μmol/L). Molecular docking indicated that although 3m, 6a, and Q2 binding the active pocket of OfHex1 in similar mode, compound 3m engaged better than the other compounds in intermolecular interaction with OfHex1.
- OfHex1 inhibitors,
- Structure-activity relationship,
- Naphthalimide derivatives,
- Quinoline derivatives,
- Molecular docking
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