Synthesis of new triazole linked carbohybrids with ROS-mediated toxicity in breast cancer

Abstract

Carbohybrids are an important class of molecules which exhibit diverse biological activities and are present as structural motifs in many natural products. Two series of new triazole linked N-glycosides of coumarins and quinolones (n = 27) were efficiently synthesized starting from 1-azido-2,3,4,6-tetra-O-acetyl β-D-glucose and 1-azido-2,3,4,6-tetra-O-acetyl β-D-galactose reacting with various 4-O-propargyl coumarins and 4-O-propargyl quinolones in shorter reaction time (30 min) under microwave assisted conditions. Anticancer activity of these newly synthesized triazole linked N-glycosides of coumarins and quinolones was determined in detail through cellular assays against MCF-7 (breast cancer cell line), HepG2 (liver cancer cell line), HCT-116 (colon cancer cell line) and Huh-7.5 cell lines. The selected library member displayed low micromolar (IC₅₀ 10.97 μM) and selective toxicity against the breast cancer cell line (MCF-7). Mechanistic studies showed that the anticancer activity of the active compound was because of the generation of reactive oxygen species (ROS).