RESUMO
Selenoindirubins and selenoindirubin-N-glycosides were prepared by the reaction of isatins and isatin-N-glycosides with 3-acetoxy-benzo[b]selenophene, respectively. While selenoindirubin-N-glycosides have not been reported before, three non-glycosylated selenoindirubins were previously reported, but without quantities, yields, scales, experimental details and spectroscopic data. In addition, the work could, in our hands, not be reproduced to prepare pure products. The present paper includes an optimized procedure for the synthesis of selenoindirubins and their complete characterization. Both selenoindirubins and selenoindirubin-N-glycosides showed antiproliferative activity in lung cancer cell lines. In melanoma cells, antiproliferative effects were further accompanied by induced apoptosis in combination with the death ligand TRAIL.
Assuntos
Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Glicosídeos/síntese química , Indóis/síntese química , Compostos Organosselênicos/síntese química , Antineoplásicos/química , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Glicosídeos/química , Humanos , Indóis/química , Conformação Molecular , Compostos Organosselênicos/química , Relação Estrutura-Atividade , Células Tumorais CultivadasRESUMO
Jatropha gossypifolia root bark is used in ethnomedicine for bacterial infections and cancer of the lungs. Phytochemical investigation resulted in the isolation and characterization of a potent anticancer and novel lathyrane diterpenoid compound, abiodone, with an unusual methylene group. The structure of this novel compound was established by 1D, and 2D NMR spectroscopic experiments a nd confirmed by X-ray analysis.