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Discovery of Rhodanine Inhibitors Targeting Of ChtI Based on the π-Stacking Effect and Aqueous Solubility.
- Source :
-
Journal of agricultural and food chemistry [J Agric Food Chem] 2023 Dec 06; Vol. 71 (48), pp. 18685-18695. Date of Electronic Publication: 2023 Nov 25. - Publication Year :
- 2023
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Abstract
- 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 π-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 <subscript>i</subscript> = 4.0 μM; IBd : K <subscript>i</subscript> = 2.2 μM) 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 <subscript>i</subscript> = 21.6 μM; IIBd : K <subscript>i</subscript> = 14.3 μM) 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 <subscript>i</subscript> = 2.4 μM) 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 π-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.
Details
- Language :
- English
- ISSN :
- 1520-5118
- Volume :
- 71
- Issue :
- 48
- Database :
- MEDLINE
- Journal :
- Journal of agricultural and food chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 38006338
- Full Text :
- https://doi.org/10.1021/acs.jafc.3c05287