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

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

doi:10.1021/acs.jafc.3c05287

Cited by 3 publications

(1 citation statement)

References 38 publications

(88 reference statements)

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“…Newly emerged adult worker bees (<24 h) were reared and treated throughout the test, which was conducted in a dark artificial climate chamber at a temperature of 23 According to our previous study, piperine-based butenolide compounds (5a−f) were reported to have excellent inhibitory potency against Of ChtI (K i values from 1.03 to 2.04 μM), and the introduction of a butenolide skeleton could enhance πstacking interactions with some key residues in the Of ChtI binding cavity. 39 Other reports further elaborated on the significance of introducing a conjugated plane for inhibitory activity of chitinase inhibitor against Of ChtI or Of Chi-h. 20,42 Therefore, the previously reported piperine-based butenolide compound 5f was selected as a lead compound in this work. The basic butenolide skeleton of 5f was retained, and benzo[d] [1,3]dioxole was replaced with a more economical benzene ring based on the reported inhibitory mechanism of chitinase inhibitors.…”

Section: Growth Inhibition Effectsmentioning

confidence: 99%

Novel Butenolide Derivatives as Dual-Chitinase Inhibitors to Arrest the Growth and Development of the Asian Corn Borer

Zou,

Li,

Jiang

et al. 2024

J. Agric. Food Chem.

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Of ChtI and Of Chi-h are considered potential targets for the control of Asian corn borer (Ostrinia furnacalis). In this work, the previously reported Of ChtI inhibitor 5f was found to show certain inhibitory activity against Of Chi-h (K i = 5.81 μM). Two series of novel butenolide derivatives based on lead compound 5f were designed with the conjugate skeleton, contributing to the π-binding interaction to chitinase, and then synthesized. Compounds 4a−l and 7a−p displayed excellent inhibitory activities against Of ChtI and Of Chi-h, respectively, at a concentration of 10 μM. Compound 4h was found to be a good dual-Chitinase inhibitor, with K i values of 1.82 and 2.00 μM against Of ChtI and Of Chi-h, respectively. The inhibitory mechanism studies by molecular docking suggested that π−π stacking interactions were crucial to the inhibitory activity of novel butenolide derivatives against two different chitinases. A preliminary bioassay indicated that 4h exhibited certain growth inhibition effects against O. furnacalis. Butenolide-like analogues should be further studied as promising novel dual-chitinase inhibitor candidates for the control of O. furnacalis.

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