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

Overview

Journal J Agric Food Chem

Specialties Chemistry
Nutritional Sciences

Date 2022 Dec 22

PMID 36548787

Authors

Francisco J R Mejias

Suhang He

Rosa M Varela

Jose M G Molinillo

Andrea Barba-Bon

Werner M Nau

Francisco A Macias

Affiliations

Soon will be listed here.

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 (). Computational studies show that 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 (, = (1.85 ± 0.37) × 10 M; , = (3.91 ± 0.53) × 10 M; and , = (1.27 ± 0.42) × 10 M). NMR characterization and stability analysis were also performed and revealed an interesting p modulation and stabilization by cucurbiturils (2-amino-3-phenoxazin-3-one (), p = 2.94 ± 0.30, and p = 4.12 ± 0.15; 2,2'-disulfanediyldianiline (), p = 2.14 ± 0.09, and , p = 3.26 ± 0.09), thus favoring applications in different kinds of crop soils. Kinetic studies have demonstrated the stability of the complex at different pH media for more than 90 min. An in vitro bioassay with etiolated wheat coleoptiles showed that the bioactivity of and is enhanced upon complexation.

Citing Articles

Supramolecular complexation of phenylephrine by cucurbit[7]uril in aqueous solution.

Assaf K, Faraj A, Abu-Nameh E, Alnajjar M RSC Adv. 2024; 14(19):13286-13290.

PMID: 38655473 PMC: 11037392. DOI: 10.1039/d4ra01910e.

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