Molecular Topology QSAR Strategy for Crop Protection: New Natural Fungicides with Chitin Inhibitory Activity

Gálvez-Llompart, María; Zanni, Riccardo; Gálvez, Jorge; García-Domènech, Ramón

doi:10.1021/acsomega.0c00177

Cited by 5 publications

(5 citation statements)

References 46 publications

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“…In addition, it focuses on the interconnection of atoms inside molecules rather than on geometric characteristics such as angles, distances, or three-dimensional structures, which are often addressed in traditional methodologies ( Gálvez-Llompart et al., 2013 ; Zanni et al., 2015 ). MT has recently become the most common and effective plant protection approach used by researchers ( Zanni et al., 2019 ; Galvez-Llompart et al., 2020 ). MT was also used to predict the fungicidal activity of various diphenylamine derivatives against three fungal species namely rice blast cucumber downy mildew, and cucumber grey mold ( Zanni et al., 2019 ).…”

Section: Plant Pathogenic Fungal Cda Inhibitionmentioning

confidence: 99%

The molecular structure, biological roles, and inhibition of plant pathogenic fungal chitin deacetylases

Mapuranga,

Chang,

et al. 2024

Front. Plant Sci.

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Chitin/polysaccharide deacetylases belong to the carbohydrate esterases family 4 (CE4 enzymes). They play a crucial role in modifying the physiochemical characteristics of structural polysaccharides and are also involved in a wide range of biological processes such as fungal autolysis, spore formation, cell wall formation and integrity, and germling adhesion. These enzymes are mostly common in fungi, marine bacteria, and a limited number of insects. They facilitate the deacetylation of chitin which is a structural biopolymer that is abundantly found in fungal cell walls and spores and also in the cuticle and peritrophic matrices of insects. The deacetylases exhibit specificity towards a substrate containing a sequence of four GlcNAc units, with one of these units being subjected to deacetylation. Chitin deacetylation results in the formation of chitosan, which is a poor substrate for host plant chitinases, therefore it can suppress the host immune response triggered by fungal pathogens and enhance pathogen virulence and colonization. This review discusses plant pathogenic fungal chitin/polysaccharide deacetylases including their structure, substrate specificity, biological roles and some recently discovered chitin deacetylase inhibitors that can help to mitigate plant fungal diseases. This review provides fundamental knowledge that will undoubtedly lead to the rational design of novel inhibitors that target pathogenic fungal chitin deacetylases, which will also aid in the management of plant diseases, thereby safeguarding global food security.

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Section: Plant Pathogenic Fungal Cda Inhibitionmentioning

confidence: 99%

The molecular structure, biological roles, and inhibition of plant pathogenic fungal chitin deacetylases

Mapuranga,

Chang,

et al. 2024

Front. Plant Sci.

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“…Therefore, the active search for new active agents to counteract these pests is needed [8]. For this search, the aid of computational methods, such as QSAR [9,10], is increasingly being used in the development of new derivatives of known fungicides [11], in the design of new libraries for computational screening [12], in the identification of new lead structures [13] and in the screening of natural products [14].…”

Section: Introductionmentioning

confidence: 99%

Application of SSIR Method for the Design of Fungicides

Julián-Ortiz

Besalú

2023

Applied Sciences

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The design of fungicides is a central topic in agricultural chemistry. In this manuscript, it is shown how the Superposition of Significant Interaction Rules (SSIR) method can serve the generation of new potentially active molecules. By using SSIR, it is shown how the process becomes a simple symbolic procedure without the intervention of sophisticated statistical methods, although the results obtained are comparable.

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“…The methodology allows a fast and precise prediction of many biological and physicochemical properties. − Defined as a part of mathematical chemistry, MT is related to the assimilation between molecules and graphs, , so that it can depict molecular structures through graph theoretical indices. , Besides, it deals with the connectivity of atoms in molecules and not with geometrical features such as angles, distances, or tridimensional structures, which are common in standard/conventional approaches. , This way, graph theory and surrounding disciplines stand as basic tools for MT development. By this approach, excellent results have been obtained in the design and selection of new drugs for different pharmacological fields − and more recently in crop protection. , …”

Section: Introductionmentioning

confidence: 99%

“…By this approach, excellent results have been obtained in the design and selection of new drugs for different pharmacological fields 23−25 and more recently in crop protection. 26,27 The fungal cell wall is a preferred and safe target for fungicides. Most of the major cell wall components and enzymes that assemble them are not present in humans, other mammals, or plants.…”

Section: Introductionmentioning

confidence: 99%

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Rational Design of Chitin Deacetylase Inhibitors for Sustainable Agricultural Use Based on Molecular Topology

Zanni

Martínez-Cruz

Gálvez-Llompart

et al. 2022

J. Agric. Food Chem.

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Fungicide resistance is a major concern in modern agriculture; therefore, there is a pressing demand to develop new, greener chemicals. Chitin is a major component of the fungal cell wall and a well-known elicitor of plant immunity. To overcome chitin recognition, fungal pathogens developed different strategies, with chitin deacetylase (CDA) activity being the most conserved. This enzyme is responsible for hydrolyzing the N-acetamido group in N-acetylglucosamine units of chitin to convert it to chitosan, a compound that can no longer be recognized by the plant. In previous works, we observed that treatments with CDA inhibitors, such as carboxylic acids, reduced the symptoms of cucurbit powdery mildew and induced rapid activation of chitin-triggered immunity, indicating that CDA could be an interesting target for fungicide development. In this work, we developed an in silico strategy based on QSAR (quantitative structure-activity relationship) and molecular topology (MT) to discover new, specific, and potent CAD inhibitors. Starting with the chemical structures of few carboxylic acids, with and without disease control activity, three predictive equations based on the MT paradigm were developed to identify a group of potential molecules. Their fungicidal activity was experimentally tested, and their specificity as CDA inhibitors was studied for the three best candidates by molecular docking simulations. To our knowledge, this is the first time that MT has been used for the identification of potential CDA inhibitors to be used against resistant powdery mildew strains. In this sense, we consider of special interest the discovery of molecules capable of stimulating the immune system of plants by triggering a defensive response against fungal species that are highly resistant to fungicides such as powdery mildew.

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Molecular Topology QSAR Strategy for Crop Protection: New Natural Fungicides with Chitin Inhibitory Activity

Cited by 5 publications

References 46 publications

The molecular structure, biological roles, and inhibition of plant pathogenic fungal chitin deacetylases

The molecular structure, biological roles, and inhibition of plant pathogenic fungal chitin deacetylases

Application of SSIR Method for the Design of Fungicides

Rational Design of Chitin Deacetylase Inhibitors for Sustainable Agricultural Use Based on Molecular Topology

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