Synthesis and antimetastatic activity evaluation of cinnamic acid derivatives containing 1,2,3-triazolic portions

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dc.creatorLima, Graziela Domingues de Almeida
dc.creatorRodrigues, Michelle Peixoto
dc.creatorMendes, Tiago Antônio de Oliveira
dc.creatorMoreira, Gabriela Alves
dc.creatorSiqueira, Raoni Pais
dc.creatorSilva, Adalberto Manoel da
dc.creatorVaz, Boniek Gontijo
dc.creatorFietto, Juliana Lopes Rangel
dc.creatorBressan, Gustavo Costa
dc.creatorNeves, Mariana Machado
dc.date.accessioned2023-08-03T15:25:26Z
dc.date.available2023-08-03T15:25:26Z
dc.date.issued2018
dc.description.abstractIt is herein described the preparation and evaluation of antimetastatic activity of twenty-six cinnamic acid derivatives containing 1,2,3-triazolic portions. The compounds were prepared using as the key step the Copper(I)-catalyzed azide (A)-alkyne (A) cycloaddition (C) (CuAAC reaction), also known as click reaction, between alkynylated cinnamic acid derivatives and different benzyl azides. The reactions were carried in CH2Cl2/H2O (1:1 v/v) at room temperature, and the triazole derivatives were obtained in yields ranging from 73%single bond99%. Reaction times varied from 5 to 40 min. The identity of the synthesized compounds was confirmed by IR and NMR (1H and 13C) spectroscopic techniques. They were then submitted to in vitro bioassays to investigate how they act over metastatic behavior of murine melanoma. The most potent compound, namely 3-(1-benzyl-1H-1,2,3-triazol-4-yl)propyl cinnamate (9a), showed significant antimetastatic and antiproliferative activities against B16-F10 cells. In addition, gelatin zymography and molecular docking analyses pointed to the fact that this compound has potential to interact with matrix metalloproteinase 9 (MMP-9) and MMP-2, which are directly involved in melanoma progression. Therefore, these findings suggest that cinnamic acid derivatives containing 1,2,3-triazolic portions may have potential for development of novel candidates for controlling malignant metastatic melanoma.pt_BR
dc.identifier.citationLIMA, Graziela Domingues de Almeida et al. Synthesis and antimetastatic activity evaluation of cinnamic acid derivatives containing 1,2,3-triazolic portions. Toxicology in Vitro, Amsterdam, v. 53, p. 1-9, 2018. DOI: 10.1016/j.tiv.2018.07.015. Disponível em: https://www.sciencedirect.com/science/article/abs/pii/S0887233318303874?via%3Dihub. Acesso em: 28 jun. 2023.pt_BR
dc.identifier.doi10.1016/j.tiv.2018.07.015
dc.identifier.issn0887-2333
dc.identifier.issne- 1879-3177
dc.identifier.urihttps://www.sciencedirect.com/science/article/abs/pii/S0887233318303874?via%3Dihub
dc.language.isoengpt_BR
dc.publisher.countryHolandapt_BR
dc.publisher.departmentInstituto de Química - IQ (RMG)pt_BR
dc.rightsAcesso Restritopt_BR
dc.subjectCinnamic acidpt_BR
dc.subject1,2,3-triazolespt_BR
dc.subjectAntimetastaticpt_BR
dc.subjectMelanomapt_BR
dc.subjectClick chemistrypt_BR
dc.subjectGelatinasespt_BR
dc.subjectMatrix metalloproteinasept_BR
dc.subjectVirtual molecular dockingpt_BR
dc.titleSynthesis and antimetastatic activity evaluation of cinnamic acid derivatives containing 1,2,3-triazolic portionspt_BR
dc.typeArtigopt_BR

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