Synthesis of new 2-galactosylthiazolidine-4-carboxylic acid amides. Antitumor evaluation against melanoma and breast cancer cells

A set of 2-galactosylthiazolidine-4-carboxylic acid amides was synthesized with different length for the carbon chain amide moiety. The cytotoxicity of the molecules was evaluated against A375 melanoma and MCF7 breast cancer cell lines. For the derivatives tested, the one that contains a C16 amide carbon chain is the most active with an IC50 of 17.0 μM for A375 and 5.8 μM for MCF7. This compound also shows cytotoxicity in the triple negative cancer cell line HCC1806. The selectivity of the compounds was assessed by comparing the cytotoxicity in cancer cell line versus in a fibroblast cell line. Flow cytometry studies show the activation of apoptotic pathways and also DNA damages with blockage of the cell cycle in the S-phase and appearance of peaks in G0/G1-phase.

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► Thiazolidine ring presents diversified biological properties.
► New 2-galactosylthiazolidine-4-carboxylic acid amides were prepared by simple routes.
► The compounds showed anti-proliferative properties against A375 melanoma and MCF7 breast cancer cells.
► The more active compound 11 showed a IC50 of 12.6 ± 1.8 μM for a triple negative cancer cell line, a very aggressive cancer type.