RESUMO
A bis-triazolyl phenylalaninyl galactoside was synthesized by a two-fold click reaction between an azido phenylalanine and a di-O-propynyl galactoside. By a cytotoxicity assay the compound was determined to be selectively toxic for multiple myeloma (MM) among a series of cancer cell lines with no toxicity to a control cell line. A Western blot analysis suggested that this compound could potentiate the cleavage of poly ADP-ribose polymerase in MM cells, leading to apoptosis.
Assuntos
Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Mieloma Múltiplo/tratamento farmacológico , Antineoplásicos/química , Apoptose/efeitos dos fármacos , Linhagem Celular Tumoral/efeitos dos fármacos , Química Click , Ensaios de Seleção de Medicamentos Antitumorais , Glicosídeos/química , Humanos , Mieloma Múltiplo/patologia , Poli(ADP-Ribose) Polimerases/metabolismoRESUMO
Glycoligands, which feature a glycoside as the central template incorporating Lewis bases as metal chelation sites and various fluorophores as the chemical reporter, represent a range of interesting scaffolds for development of chemosensors. Here, new types of triazolyl bidentate glycoligands (TBGs) based on the grafting of 3-azidocoumarin to the C2,3- or C4,6-positions of three epimeric pyranoglycosides including a glucoside, a galactoside, and a mannoside were efficiently synthesized via a fluorogenic dual click reaction assisted by microwave irradiation. The desired TBGs were afforded in high conversion rates (>90%) and reasonable yields (â¼70%). Moreover, a preliminary optical study of two hydroxyl-free glucoside-based TBGs indicates that these compounds are strongly fluorescent in pure water, implying their potential for ion detections in aqueous media.
