Discovery of Rhodanine Inhibitors Targeting Of ChtI Based on the π-Stacking Effect and Aqueous Solubility

文献类型： 外文期刊

第一作者： Han, Qing

作者： Han, Qing;Zhang, Jingyu;Feng, Tianyu;Zi, Yunjiang;Zhang, Rulei;Zou, Renxuan;Liu, Yaoyang;Duan, Hongxia;Han, Qing;Zhang, Jingyu;Feng, Tianyu;Zi, Yunjiang;Zhang, Rulei;Zou, Renxuan;Liu, Yaoyang;Duan, Hongxia;Wu, Nan;Yang, Qing;Yang, Qing

作者机构：

关键词： Of ChtI; rhodanine analogues; pi-stacking effect; aqueoussolubility; insectgrowth and regulator agents

期刊名称：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY （ 影响因子：6.1； 五年影响因子：6.3 ）

ISSN： 0021-8561

年卷期： 2023 年 71 卷 48 期

页码：

收录情况： SCI

摘要： The application of some reported inhibitors against the chitinolytic enzyme Of ChtI was limited due to their unsatisfactory insecticidal activities. Hence, we first performed a synergetic design strategy combining the pi-stacking effect with aqueous solubility to find novel rhodanine analogues with inhibitory activities against Of ChtI. Novel rhodanine compounds IAa-f and IBa-f have weak aqueous solubility, but they (IAd: K-i = 4.0 mu M; IBd: K-i = 2.2 mu M) showed better inhibitory activities against Of ChtI and comparable insecticidal efficiency toward Ostrinia furnacalis compared to the high aqueous solubility compounds IIAa-f and IIBa-f (IIAd: K-i = 21.6 mu M; IIBd: K-i = 14.3 mu M) without a large conjugate plane. Further optimized compounds IIIAa-j with a conjugate plane as well as a higher aqueous solubility exhibited similar good inhibitory activities against Of ChtI (IIIAe: K-i = 2.4 mu M) and better insecticidal potency (IIIAe: mortality rate of 63.33%) compared to compounds IAa-f and IBa-f, respectively. Molecular docking studies indicated that the conjugate planarity with the pi-stacking effect for rhodanine analogues is responsible for their enzyme inhibitory activity against Of ChtI. This study provides a new strategy for designing insect chitinolytic enzyme inhibitors as insect growth regulators for pest control.

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