Inhibitory Potential of New Phenolic Hydrazide-Hydrazones with a Decoy Substrate Fragment towards Laccase from a Phytopathogenic Fungus: SAR and Molecular Docking Studies

Laccase from pathogenic fungi participates in both the delignification and neutralization of phytoantibiotics. Furthermore, it interferes with the hormone signaling in plants and catalyzes melanization. Infections of these pathogens contribute to loss in forestry, agriculture, and horticulture. As t...

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Autores principales:	Halina Maniak, Michał Talma, Mirosław Giurg
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	fungal oxidoreductase electron-rich arene derivatives enzyme kinetics molecular modeling structure-activity relationship Biology (General) QH301-705.5 Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/be850aeb77424c29b86f0ba54a2d66e8
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spelling	oai:doaj.org-article:be850aeb77424c29b86f0ba54a2d66e82021-11-25T17:55:16ZInhibitory Potential of New Phenolic Hydrazide-Hydrazones with a Decoy Substrate Fragment towards Laccase from a Phytopathogenic Fungus: SAR and Molecular Docking Studies10.3390/ijms2222123071422-00671661-6596https://doaj.org/article/be850aeb77424c29b86f0ba54a2d66e82021-11-01T00:00:00Zhttps://www.mdpi.com/1422-0067/22/22/12307https://doaj.org/toc/1661-6596https://doaj.org/toc/1422-0067Laccase from pathogenic fungi participates in both the delignification and neutralization of phytoantibiotics. Furthermore, it interferes with the hormone signaling in plants and catalyzes melanization. Infections of these pathogens contribute to loss in forestry, agriculture, and horticulture. As there is still a need to expand knowledge on efficient defense strategies against phytopathogenic fungi, the present study aimed to reveal more information on the molecular mechanisms of laccase inhibition with natural and natural-like carboxylic acid semi-synthetic derivatives. A set of hydrazide-hydrazones derived from carboxylic acids, generally including electron-rich arene units that serve as a decoy substrate, was synthesized and tested with laccase from <i>Trametes versicolor</i>. The classic synthesis of the title inhibitors proceeded with good to almost quantitative yield. Ninety percent of the tested molecules were active in the range of <i>K</i><sub>I</sub> = 8–233 µM and showed different types of action. Such magnitude of inhibition constants qualified the hydrazide-hydrazones as strong laccase inhibitors. Molecular docking studies supporting the experimental data explained the selected derivatives’ interactions with the enzyme. The results are promising in developing new potential antifungal agents mitigating the damage scale in the plant cultivation, gardening, and horticulture sectors.Halina ManiakMichał TalmaMirosław GiurgMDPI AGarticlefungal oxidoreductaseelectron-rich arene derivativesenzyme kineticsmolecular modelingstructure-activity relationshipBiology (General)QH301-705.5ChemistryQD1-999ENInternational Journal of Molecular Sciences, Vol 22, Iss 12307, p 12307 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	fungal oxidoreductase electron-rich arene derivatives enzyme kinetics molecular modeling structure-activity relationship Biology (General) QH301-705.5 Chemistry QD1-999
spellingShingle	fungal oxidoreductase electron-rich arene derivatives enzyme kinetics molecular modeling structure-activity relationship Biology (General) QH301-705.5 Chemistry QD1-999 Halina Maniak Michał Talma Mirosław Giurg Inhibitory Potential of New Phenolic Hydrazide-Hydrazones with a Decoy Substrate Fragment towards Laccase from a Phytopathogenic Fungus: SAR and Molecular Docking Studies
description	Laccase from pathogenic fungi participates in both the delignification and neutralization of phytoantibiotics. Furthermore, it interferes with the hormone signaling in plants and catalyzes melanization. Infections of these pathogens contribute to loss in forestry, agriculture, and horticulture. As there is still a need to expand knowledge on efficient defense strategies against phytopathogenic fungi, the present study aimed to reveal more information on the molecular mechanisms of laccase inhibition with natural and natural-like carboxylic acid semi-synthetic derivatives. A set of hydrazide-hydrazones derived from carboxylic acids, generally including electron-rich arene units that serve as a decoy substrate, was synthesized and tested with laccase from <i>Trametes versicolor</i>. The classic synthesis of the title inhibitors proceeded with good to almost quantitative yield. Ninety percent of the tested molecules were active in the range of <i>K</i><sub>I</sub> = 8–233 µM and showed different types of action. Such magnitude of inhibition constants qualified the hydrazide-hydrazones as strong laccase inhibitors. Molecular docking studies supporting the experimental data explained the selected derivatives’ interactions with the enzyme. The results are promising in developing new potential antifungal agents mitigating the damage scale in the plant cultivation, gardening, and horticulture sectors.
format	article
author	Halina Maniak Michał Talma Mirosław Giurg
author_facet	Halina Maniak Michał Talma Mirosław Giurg
author_sort	Halina Maniak
title	Inhibitory Potential of New Phenolic Hydrazide-Hydrazones with a Decoy Substrate Fragment towards Laccase from a Phytopathogenic Fungus: SAR and Molecular Docking Studies
title_short	Inhibitory Potential of New Phenolic Hydrazide-Hydrazones with a Decoy Substrate Fragment towards Laccase from a Phytopathogenic Fungus: SAR and Molecular Docking Studies
title_full	Inhibitory Potential of New Phenolic Hydrazide-Hydrazones with a Decoy Substrate Fragment towards Laccase from a Phytopathogenic Fungus: SAR and Molecular Docking Studies
title_fullStr	Inhibitory Potential of New Phenolic Hydrazide-Hydrazones with a Decoy Substrate Fragment towards Laccase from a Phytopathogenic Fungus: SAR and Molecular Docking Studies
title_full_unstemmed	Inhibitory Potential of New Phenolic Hydrazide-Hydrazones with a Decoy Substrate Fragment towards Laccase from a Phytopathogenic Fungus: SAR and Molecular Docking Studies
title_sort	inhibitory potential of new phenolic hydrazide-hydrazones with a decoy substrate fragment towards laccase from a phytopathogenic fungus: sar and molecular docking studies
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/be850aeb77424c29b86f0ba54a2d66e8
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Inhibitory Potential of New Phenolic Hydrazide-Hydrazones with a Decoy Substrate Fragment towards Laccase from a Phytopathogenic Fungus: SAR and Molecular Docking Studies

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