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Novel mandelic acid derivatives containing piperazinyls as potential candidate fungicides against Monilinia fructicola: Design, synthesis and mechanism study.
- Source :
-
Bioorganic chemistry [Bioorg Chem] 2024 Oct; Vol. 151, pp. 107647. Date of Electronic Publication: 2024 Jul 15. - Publication Year :
- 2024
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Abstract
- Brown rot of stone fruit, a disease caused by the ascomycete fungus Monilinia fructicola, has caused significant losses to the agricultural industry. In order to explore and discover potential fungicides against M. fructicola, thirty-one novel mandelic acid derivatives containing piperazine moieties were designed and synthesized based on the amide skeleton. Among them, target compound Z <subscript>31</subscript> exhibited obvious in vitro antifungal activity with the EC <subscript>50</subscript> value of 11.8 mg/L, and significant effects for the postharvest pears (79.4 % protective activity and 70.5 % curative activity) at a concentration of 200 mg/L. Antifungal activity for the target compounds was found to be significantly improved by the large steric hindrance of the R <subscript>1</subscript> groups and the electronegative of the piperazines in the molecular structure, according to a three-dimensional quantitative structure-activity relationship (3D-QSAR) analysis. Further mechanism studies have demonstrated that the compound Z <subscript>31</subscript> can disrupt cell membrane integrity, resulting in increased membrane permeability, release of intracellular electrolytes, and affect the normal growth of hyphae. Additional, morphological study also indicated that Z <subscript>31</subscript> may disrupt the integrity of the membrane by inducing generate excess endogenous reactive oxygen species (ROS) and resulting in the peroxidation of cellular lipids, which was further verified by the detection of malondialdehyde (MDA) content. These studies have provided the basis for the creation of novel fungicides to prevent brown rot in stone fruits.<br />Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.<br /> (Copyright © 2024 Elsevier Inc. All rights reserved.)
- Subjects :
- Antifungal Agents pharmacology
Antifungal Agents chemical synthesis
Antifungal Agents chemistry
Dose-Response Relationship, Drug
Molecular Structure
Piperazines pharmacology
Piperazines chemistry
Piperazines chemical synthesis
Quantitative Structure-Activity Relationship
Benzyl Compounds chemical synthesis
Benzyl Compounds chemistry
Benzyl Compounds pharmacology
Ascomycota drug effects
Drug Design
Fungicides, Industrial pharmacology
Fungicides, Industrial chemical synthesis
Fungicides, Industrial chemistry
Mandelic Acids pharmacology
Mandelic Acids chemistry
Microbial Sensitivity Tests
Subjects
Details
- Language :
- English
- ISSN :
- 1090-2120
- Volume :
- 151
- Database :
- MEDLINE
- Journal :
- Bioorganic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 39024805
- Full Text :
- https://doi.org/10.1016/j.bioorg.2024.107647