Molecular Docking and Quantum Studies of Lawsone Dimers Derivatives: New Investigation of Antioxidant Behavior and Antifungal Activity.


Journal

Current topics in medicinal chemistry
ISSN: 1873-4294
Titre abrégé: Curr Top Med Chem
Pays: United Arab Emirates
ID NLM: 101119673

Informations de publication

Date de publication:
2020
Historique:
received: 08 09 2019
revised: 07 11 2019
accepted: 02 12 2019
pubmed: 24 12 2019
medline: 27 11 2020
entrez: 24 12 2019
Statut: ppublish

Résumé

In general, fungal species are characterized by their opportunistic character and can trigger various infections in immunocompromised hosts. The emergence of infections associated with high mortality rates is due to the resistance mechanisms that these species develop. This phenomenon of resistance denotes the need for the development of new and effective therapeutic approaches. In this paper, we report the investigation of the antioxidant and antifungal behavior of dimeric naphthoquinones derived from lawsone whose antimicrobial and antioxidant potential has been reported in the literature. Seven fungal strains were tested, and the antioxidant potential was tested using the combination of the methodologies: reducing power, total antioxidant capacity and cyclic voltammetry. Molecular docking studies (PDB ID 5V5Z and 1EA1) were conducted which allowed the derivation of structureactivity relationships (SAR). Compound 1-i, derived from 3-methylfuran-2-carbaldehyde showed the highest antifungal potential with an emphasis on the inhibition of Candida albicans species (MIC = 0.5 µg/mL) and the highest antioxidant potential. A combination of molecular modeling data and in vitro assays can help to find new solutions to this major public health problem.

Sections du résumé

BACKGROUND BACKGROUND
In general, fungal species are characterized by their opportunistic character and can trigger various infections in immunocompromised hosts. The emergence of infections associated with high mortality rates is due to the resistance mechanisms that these species develop.
METHODS METHODS
This phenomenon of resistance denotes the need for the development of new and effective therapeutic approaches. In this paper, we report the investigation of the antioxidant and antifungal behavior of dimeric naphthoquinones derived from lawsone whose antimicrobial and antioxidant potential has been reported in the literature.
RESULTS RESULTS
Seven fungal strains were tested, and the antioxidant potential was tested using the combination of the methodologies: reducing power, total antioxidant capacity and cyclic voltammetry. Molecular docking studies (PDB ID 5V5Z and 1EA1) were conducted which allowed the derivation of structureactivity relationships (SAR). Compound 1-i, derived from 3-methylfuran-2-carbaldehyde showed the highest antifungal potential with an emphasis on the inhibition of Candida albicans species (MIC = 0.5 µg/mL) and the highest antioxidant potential.
CONCLUSION CONCLUSIONS
A combination of molecular modeling data and in vitro assays can help to find new solutions to this major public health problem.

Identifiants

pubmed: 31868147
pii: CTMC-EPUB-103133
doi: 10.2174/1568026620666191223092723
doi:

Substances chimiques

Antifungal Agents 0
Antioxidants 0
Naphthoquinones 0
Reactive Oxygen Species 0
lawsone TLH4A6LV1W

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

182-191

Informations de copyright

Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.net.

Auteurs

Aldo S de Oliveira (AS)

Department of Exact Sciences and Education, Federal University of Santa Catarina, (UFSC), Blumenau, SC, Brazil.
Laboratory of Medicinal and Computational Chemistry, Center for Research and Innovation in Biodiversity and Drug Discovery, Institute of Physics of Sao Carlos, University of Sao Paulo, Sao Carlos, SP, Brazil.

David L Palomino-Salcedo (DL)

Laboratory of Medicinal and Computational Chemistry, Center for Research and Innovation in Biodiversity and Drug Discovery, Institute of Physics of Sao Carlos, University of Sao Paulo, Sao Carlos, SP, Brazil.

Eduardo Zapp (E)

Department of Exact Sciences and Education, Federal University of Santa Catarina, (UFSC), Blumenau, SC, Brazil.

Daniela Brondani (D)

Department of Exact Sciences and Education, Federal University of Santa Catarina, (UFSC), Blumenau, SC, Brazil.

Thaynara D Hoppe (TD)

Department of Exact Sciences and Education, Federal University of Santa Catarina, (UFSC), Blumenau, SC, Brazil.

Patrícia B Brondani (PB)

Department of Exact Sciences and Education, Federal University of Santa Catarina, (UFSC), Blumenau, SC, Brazil.

Lidiane Meier (L)

Department of Exact Sciences and Education, Federal University of Santa Catarina, (UFSC), Blumenau, SC, Brazil.

Susana Johann (S)

Department of Microbiology, Federal University of Minas Gerais, Belo Horizonte, Minas Gerais, Brazil.

Leonardo L G Ferreira (LLG)

Laboratory of Medicinal and Computational Chemistry, Center for Research and Innovation in Biodiversity and Drug Discovery, Institute of Physics of Sao Carlos, University of Sao Paulo, Sao Carlos, SP, Brazil.

Adriano D Andricopulo (AD)

Laboratory of Medicinal and Computational Chemistry, Center for Research and Innovation in Biodiversity and Drug Discovery, Institute of Physics of Sao Carlos, University of Sao Paulo, Sao Carlos, SP, Brazil.

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Classifications MeSH