Thio-sugars VII. Effect of 3-deoxy-4-S-(β-d-gluco- and β-d-galactopyranosyl)-4-thiodisaccharides and their sulfoxides and sulfones on the viability and growth of selected murine and human tumor cell lines Original Research Article

The first conversion of (1→4)-thiodisaccharides into corresponding sulfoxides and sulfones by conventional oxidation with m-chloroperoxybenzoic acid (MCPBA) is reported. The effects of α-(1→4)-3′-deoxythiodisaccharides (8–9) and their sulfoxide (14–15) and sulfone (16–17) derivatives on murine leukemia and human colon and pancreatic carcinoma cell viability were studied. Concentrations of thio-sugars that decreased tumor cell line viability by 50% (IC50), measured via the MTT assay, ranged from 6.4 to 38.3 μg/mL. The effect of α-(1→4)-3′-deoxythiodisaccharide derivatives were most profound on human pancreatic epithelial carcinoma (PANC-1) cells with compounds 8 and 9 having IC50 values of 6.4 μg/mL and 8.2 μg/mL, respectively. Sulfone derivatives 16 and 17 also had pronounced effects on PANC-1 cell viability (IC50=10.2 μg/mL and 9.6 μg/mL, respectively). These results indicate that deoxythio-disaccharide analogs generated by functionalization of the universal chiral precursor levoglucosenone may have cytotoxic properties and therapeutic potential as anticancer agents.