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

dc.creatorLima, Graziela Domingues de Almeida
dc.creatorRodrigues, Michelle Peixoto
dc.creatorMoreira, Gabriela Alves
dc.creatorMendes, Tiago Antônio de Oliveira
dc.creatorSiqueira, Raoni Pais
dc.creatorSilva, Adalberto Manoel da
dc.creatorVaz, Boniek Gontijo
dc.creatorFietto, Juliana Lopes Rangel
dc.creatorBressan, Gustavo Costa
dc.creatorTeixeira, Róbson Ricardo
dc.creatorMachado-Neves, Mariana
dc.date2019-01-07T13:21:34Z
dc.date2019-01-07T13:21:34Z
dc.date2018-12
dc.date.accessioned2023-09-27T20:50:35Z
dc.date.available2023-09-27T20:50:35Z
dc.identifier0887-2333
dc.identifierhttps://doi.org/10.1016/j.tiv.2018.07.015
dc.identifierhttp://www.locus.ufv.br/handle/123456789/22921
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/8949188
dc.descriptionIt 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%99%. 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.
dc.formatpdf
dc.formatapplication/pdf
dc.languageeng
dc.publisherToxicology in Vitro
dc.relationVolume 53, Pages 1- 9, December 2018
dc.rights2018 Published by Elsevier Ltd.
dc.subjectCinnamic acid
dc.subject1,2,3-triazoles
dc.subjectAntimetastatic
dc.subjectMelanoma
dc.subjectClick chemistry
dc.subjectGelatinases
dc.subjectMatrix metalloproteinase
dc.subjectVirtual molecular docking
dc.titleSynthesis and antimetastatic activity evaluation of cinnamic acid derivatives containing 1,2,3-triazolic portions
dc.typeArtigo


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