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Metadados | Descrição | Idioma |
---|---|---|
Autor(es): dc.contributor | Universidade Estadual Paulista (Unesp) | - |
Autor(es): dc.contributor | Universidade Estadual de Campinas (UNICAMP) | - |
Autor(es): dc.creator | Marques, Beatriz C. [UNESP] | - |
Autor(es): dc.creator | Santos, Mariana B. [UNESP] | - |
Autor(es): dc.creator | Anselmo, Daiane B. [UNESP] | - |
Autor(es): dc.creator | Monteiro, Diego A. [UNESP] | - |
Autor(es): dc.creator | Gomes, Eleni [UNESP] | - |
Autor(es): dc.creator | Saiki, Marilia F. C. [UNESP] | - |
Autor(es): dc.creator | Rahal, Paula [UNESP] | - |
Autor(es): dc.creator | Rosalen, Pedro L. | - |
Autor(es): dc.creator | Sardi, Janaina C. O. | - |
Autor(es): dc.creator | Regasini, Luis O. [UNESP] | - |
Data de aceite: dc.date.accessioned | 2022-02-22T00:35:09Z | - |
Data de disponibilização: dc.date.available | 2022-02-22T00:35:09Z | - |
Data de envio: dc.date.issued | 2020-12-11 | - |
Data de envio: dc.date.issued | 2020-12-11 | - |
Data de envio: dc.date.issued | 2019-12-31 | - |
Fonte completa do material: dc.identifier | http://dx.doi.org/10.2174/1573406415666190724145158 | - |
Fonte completa do material: dc.identifier | http://hdl.handle.net/11449/202015 | - |
Fonte: dc.identifier.uri | http://educapes.capes.gov.br/handle/11449/202015 | - |
Descrição: dc.description | Background: 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.description | Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) | - |
Descrição: dc.description | Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) | - |
Descrição: dc.description | Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) | - |
Descrição: dc.description | Department of Chemistry and Environmental Sciences Institute of Biosciences Humanities and Exact Sciences São Paulo State University (Unesp) | - |
Descrição: dc.description | Department of Biology Institute of Bio-sciences Humanities and Exact Sciences São Paulo State University (Unesp) | - |
Descrição: dc.description | Department of Physiological Sciences Piracicaba Dental School University of Campinas (Unicamp) | - |
Descrição: dc.description | Department of Chemistry and Environmental Sciences Institute of Biosciences Humanities and Exact Sciences São Paulo State University (Unesp) | - |
Descrição: dc.description | Department of Biology Institute of Bio-sciences Humanities and Exact Sciences São Paulo State University (Unesp) | - |
Descrição: dc.description | CAPES: 001 | - |
Descrição: dc.description | FAPESP: 2009/53989-4 | - |
Descrição: dc.description | FAPESP: 2014/18330-0 | - |
Descrição: dc.description | FAPESP: 2014/18577-5 | - |
Descrição: dc.description | FAPESP: 2014/50926-0 | - |
Descrição: dc.description | FAPESP: 2016/08084-7 | - |
Descrição: dc.description | FAPESP: 2017/09245-7 | - |
Descrição: dc.description | FAPESP: 2018/ 15083-2 | - |
Descrição: dc.description | CNPq: 309957/2019-2 306251/ 2016-7 | - |
Descrição: dc.description | CNPq: 429322/2018-6 | - |
Descrição: dc.description | CNPq: 465637/2014-0 | - |
Descrição: dc.description | CNPq: 471129/2013-5 | - |
Formato: dc.format | 881-891 | - |
Idioma: dc.language | en | - |
Relação: dc.relation | Medicinal Chemistry | - |
???dc.source???: dc.source | Scopus | - |
Palavras-chave: dc.subject | Antibacterial | - |
Palavras-chave: dc.subject | Antifungal | - |
Palavras-chave: dc.subject | Antiproliferative | - |
Palavras-chave: dc.subject | Chalcone | - |
Palavras-chave: dc.subject | Drug-likeness | - |
Palavras-chave: dc.subject | Methoxyl | - |
Título: dc.title | Methoxychalcones: Effect of methoxyl group on the antifungal, antibac-terial and antiproliferative activities | - |
Tipo de arquivo: dc.type | livro digital | - |
Aparece nas coleções: | Repositório Institucional - Unesp |
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