Stability and pK_a Modulation of Aminophenoxazinones and Their Disulfide Mimics by Host-Guest Interaction with Cucurbit[7]uril. Direct Applications in Agrochemical Wheat Models.

ABSTRACT: Aqueous solubility and stability often limit the application of aminophenoxazinones and their sulfur mimics as promising agrochemicals in a sustainable agriculture inspired by allelopathy. This paper presents a solution to the problem using host-guest complexation with cucurbiturils (CBn). Computational studies show that CB7 is the most suitably sized homologue due to its strong affinity for guest molecules and its high water solubility. Complex formation has been studied by direct titrations monitored using UV-vis spectroscopy, finding a preferential interaction with protonated aminophenoxazinone species with high binding affinities (CB7·APOH⁺, K_a = (1.85 ± 0.37) × 10⁶ M^-1; CB7·DiS-NH₃

SUBMITTER: Mejias FJR 

PROVIDER: S-EPMC9837879 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature