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

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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).

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

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Publication details

The article was received on 25 Jun 2019, accepted on 01 Nov 2019 and first published on 01 Nov 2019


Article type: Paper
DOI: 10.1039/C9NJ03288F
New J. Chem., 2019, Advance Article

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

    P. Kumari, S. Dubey, S. Venkatachalapathy, C. Narayana, A. Gupta and R. Sagar, New J. Chem., 2019, Advance Article , DOI: 10.1039/C9NJ03288F

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