数字农科院2.0

Novel 5-alkenylthiothiazolidinone scaffold discovery as Multi-Chitinases inhibitors to arrest the molting of Asian corn borer

文献类型： 外文期刊

作者： Shi, Dongmei;Ji, Xinge;Zou, Renxuan;Jiang, Zhiyang;Duan, Yangwei;Han, Qing;Xu, Zhijian;Huang, Jiaxing;Yang, Qing;Duan, Hongxia

作者机构：

关键词： 5-alkenylthiothiazolidinone scaffold;Multichitinase inhibitor;Amide bond;Asian corn borer;insect growth regulator

期刊名称： JOURNAL OF MOLECULAR STRUCTURE

ISSN： 0022-2860

年卷期： 2024 年 1321 卷

页码：

收录情况： SCIE（2024版） ; ; EI（2024版）

摘要： Chitinases are crucial enzymes in insect growth and development processes and have thus become potential targets for the control of insect pests. Rhodanine (5-alkenylthiothiazolidinone) is an important fragment with various biological activities in agriculture. Therefore, 24 novel 5-alkenylthiothiazolidinone derivatives were designed and synthesized by introducing a hydrophobic hydrocarbon chain and a benzylformamide group on the basis of the conserved binding cavity of three chitinases, OfChtI, OfChtII and OfChi-h. These 5-alkenylthiothiazolidinone analogs were found for the first time to have inhibitory effects on OfChtII, except for their ability to inhibit the other two known chitinases, OfChtI and OfChi-h. The inhibitory activities of the target compounds against OfChtI and OfChi-h ranged from 40 % to 95 % at a concentration of 100 mu M. In particular, some compounds were also found to have an inhibitory rate of 50 % against OfChtII. Among them, the Ki values of the most potent compound 5e-9 were 5.82, 27.5 and 6.77 mu M against OfChtI, OfChtII and OfChi-h, respectively. The inhibition mechanism studies revealed that both pi stacking interactions and hydrophobic interactions were vital for the binding of Compound 5e-9 with the three chitinases. A lethal and sublethal bioassay study revealed that Compound 5e-9 could affect the growth and development of Asian corn borers. This work suggested that 5-alkenylthiothiazolidinone could be a novel inhibitor scaffold against multichitinase for the development of insect growth regulators.

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