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Anticancer Agents Med Chem ; 20(5): 622-633, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-31976847

RESUMO

BACKGROUND: Cancer is a multifactorial disease, representing one of the leading causes of death worldwide. On a global estimate, breast cancer is the most frequently occurring cancer in women and cervical cancer, the fourth most common. Both types of cancer remain the major cause of cancer-related mortality in developing countries. A strategy for rational drug design is hybridization, which aims to bring together in one molecule, two or more pharmacophores in order to reach several biological targets. OBJECTIVE: The objective of this work was to develop new hybrids based on natural pharmacophores: Betulinic acid (1) and brosimine b (2), active in female cancer cell lines. METHODS: The coupling reactions were carried out by Steglich esterification. Different compounds were designed for the complete and simplified structural hybridization of molecules. The anticancer activities of the compounds were evaluated in human cervical adenocarcinoma (HeLa), human cervical metastatic epidermoid carcinoma (ME-180), and human breast adenocarcinoma (MCF-7) cell lines. RESULTS: Hybrid 3 presented higher potency (IC50 = 9.2 ± 0.5µM) and SI (43.5) selectively in MCF-7 cells (in relation to Vero cells) with its cytotoxic effect occurring via apoptosis. In addition, compound 6 showed activity in MCF-7 and HeLa cells with intermediate potency, but with high efficacy, acting via apoptosis as well. CONCLUSION: In this context, we showed that the combination of two complex structures generated the development of hybrids with differing inhibitory profiles and apoptotic modes of action, thus representing potential alternatives in female cancer treatment.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Flavonoides/farmacologia , Triterpenos Pentacíclicos/farmacologia , Antineoplásicos Fitogênicos/síntese química , Antineoplásicos Fitogênicos/química , Apoptose/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Feminino , Flavonoides/síntese química , Flavonoides/química , Células HeLa , Humanos , Conformação Molecular , Moraceae/química , Triterpenos Pentacíclicos/síntese química , Triterpenos Pentacíclicos/química , Plantas Medicinais/química , Relação Estrutura-Atividade , Células Tumorais Cultivadas , Ácido Betulínico
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