Methoxychalcones: Effect of methoxyl group on the antifungal, antibac-terial and antiproliferative activities

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MetadadosDescriçãoIdioma
Autor(es): dc.contributorUniversidade Estadual Paulista (Unesp)-
Autor(es): dc.contributorUniversidade Estadual de Campinas (UNICAMP)-
Autor(es): dc.creatorMarques, Beatriz C. [UNESP]-
Autor(es): dc.creatorSantos, Mariana B. [UNESP]-
Autor(es): dc.creatorAnselmo, Daiane B. [UNESP]-
Autor(es): dc.creatorMonteiro, Diego A. [UNESP]-
Autor(es): dc.creatorGomes, Eleni [UNESP]-
Autor(es): dc.creatorSaiki, Marilia F. C. [UNESP]-
Autor(es): dc.creatorRahal, Paula [UNESP]-
Autor(es): dc.creatorRosalen, Pedro L.-
Autor(es): dc.creatorSardi, Janaina C. O.-
Autor(es): dc.creatorRegasini, Luis O. [UNESP]-
Data de aceite: dc.date.accessioned2022-02-22T00:35:09Z-
Data de disponibilização: dc.date.available2022-02-22T00:35:09Z-
Data de envio: dc.date.issued2020-12-11-
Data de envio: dc.date.issued2020-12-11-
Data de envio: dc.date.issued2019-12-31-
Fonte completa do material: dc.identifierhttp://dx.doi.org/10.2174/1573406415666190724145158-
Fonte completa do material: dc.identifierhttp://hdl.handle.net/11449/202015-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/11449/202015-
Descrição: dc.descriptionBackground: Chalcones substituted by methoxyl groups have presented a broad spec-trum of bioactivities, including antifungal, antibacterial and antiproliferative effects. However, a clear and unambiguous investigation about the relevance of this substituent on the chalcone framework has not been described. Objective: The purpose of this work is to assess the antibacterial, antifungal and antiproliferative activities of the two series of seventeen synthesized regioisomeric methoxychalcones. Series I and II were constituted by chalcones substituted by methoxyl groups on rings A (5–12) and B (13–21), respectively. In addition, the library of methoxychalcones was submitted to in silico drug-likeness and pharmacokinetics properties predictions. Methods: Methoxychalcones were synthesized and their structures were confirmed by NMR spectral data analyses. Evaluations of antimicrobial activity were performed against five species of Candida, two Gram-negative and five Gram-positive species. For antiproliferative activity, methoxychalcones were evaluated against four human tumorigenic cell lines, as well as human non-tumorigenic keratinocytes. Drug-likeness and pharmacokinetics properties were predicted using Molinspiration and PreADMET toolkits. Results: In general, chalcones of series I are the most potent antifungal, antibacterial and antipro-liferative agents. 3’, 4’, 5’-Trimethoxychalcone (12) demonstrated potent antifungal activity against Candida krusei (MIC = 3.9 µg/mL), eight times more potent than fluconazole (reference antifungal drug). 3’-Methoxychalcone (6) displayed anti-Pseudomonas activity (MIC = 7.8 µg/mL). 2’,5’-Dimethoxychalcone (9) displayed potent antiproliferative effect against C-33A (cervix), A-431 (skin) and MCF-7 (breast), with IC50 values ranging from 7.7 to 9.2 µM. Its potency was superior to curcumin (reference antiproliferative compound), which exhibited IC50 values ranging from 10.4 to 19.0 µM. Conclusion: Our studies corroborated the relevance of methoxychalcones as antifungal, antibacte-rial and antiproliferative agents. In addition, we elucidated influence of the position and number of methoxyl groups toward bioactivity. In silico predictions indicated good drug-likeness and phar-macokinetics properties to the library of methoxychalcones.-
Descrição: dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)-
Descrição: dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)-
Descrição: dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)-
Descrição: dc.descriptionDepartment of Chemistry and Environmental Sciences Institute of Biosciences Humanities and Exact Sciences São Paulo State University (Unesp)-
Descrição: dc.descriptionDepartment of Biology Institute of Bio-sciences Humanities and Exact Sciences São Paulo State University (Unesp)-
Descrição: dc.descriptionDepartment of Physiological Sciences Piracicaba Dental School University of Campinas (Unicamp)-
Descrição: dc.descriptionDepartment of Chemistry and Environmental Sciences Institute of Biosciences Humanities and Exact Sciences São Paulo State University (Unesp)-
Descrição: dc.descriptionDepartment of Biology Institute of Bio-sciences Humanities and Exact Sciences São Paulo State University (Unesp)-
Descrição: dc.descriptionCAPES: 001-
Descrição: dc.descriptionFAPESP: 2009/53989-4-
Descrição: dc.descriptionFAPESP: 2014/18330-0-
Descrição: dc.descriptionFAPESP: 2014/18577-5-
Descrição: dc.descriptionFAPESP: 2014/50926-0-
Descrição: dc.descriptionFAPESP: 2016/08084-7-
Descrição: dc.descriptionFAPESP: 2017/09245-7-
Descrição: dc.descriptionFAPESP: 2018/ 15083-2-
Descrição: dc.descriptionCNPq: 309957/2019-2 306251/ 2016-7-
Descrição: dc.descriptionCNPq: 429322/2018-6-
Descrição: dc.descriptionCNPq: 465637/2014-0-
Descrição: dc.descriptionCNPq: 471129/2013-5-
Formato: dc.format881-891-
Idioma: dc.languageen-
Relação: dc.relationMedicinal Chemistry-
???dc.source???: dc.sourceScopus-
Palavras-chave: dc.subjectAntibacterial-
Palavras-chave: dc.subjectAntifungal-
Palavras-chave: dc.subjectAntiproliferative-
Palavras-chave: dc.subjectChalcone-
Palavras-chave: dc.subjectDrug-likeness-
Palavras-chave: dc.subjectMethoxyl-
Título: dc.titleMethoxychalcones: Effect of methoxyl group on the antifungal, antibac-terial and antiproliferative activities-
Tipo de arquivo: dc.typelivro digital-
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