Thio-sugars VII. Effect of 3-deoxy-4-S-(beta-D-gluco- and beta-D-galactopyranosyl)-4-thiodisaccharides and their sulfoxides and sulfones on the viability and growth of selected murine and human tumor cell lines. Witczak, Z. J., Kaplon, P., & Dey, P. M. Carbohydrate Research, 338(1):11–18, January, 2003.
abstract   bibtex   
The first conversion of (1–\textgreater4)-thiodisaccharides into corresponding sulfoxides and sulfones by conventional oxidation with m-chloroperoxybenzoic acid (MCPBA) is reported. The effects of alpha-(1–\textgreater4)-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% (IC(50)), measured via the MTT assay, ranged from 6.4 to 38.3 microg/mL. The effect of alpha-(1–\textgreater4)-3'-deoxythiodisaccharide derivatives were most profound on human pancreatic epithelial carcinoma (PANC-1) cells with compounds 8 and 9 having IC(50) values of 6.4 microg/mL and 8.2 microg/mL, respectively. Sulfone derivatives 16 and 17 also had pronounced effects on PANC-1 cell viability (IC(50)=10.2 microg/mL and 9.6 microg/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.
@article{witczak_thio-sugars_2003,
	title = {Thio-sugars {VII}. {Effect} of 3-deoxy-4-{S}-(beta-{D}-gluco- and beta-{D}-galactopyranosyl)-4-thiodisaccharides and their sulfoxides and sulfones on the viability and growth of selected murine and human tumor cell lines},
	volume = {338},
	issn = {0008-6215},
	abstract = {The first conversion of (1--{\textgreater}4)-thiodisaccharides into corresponding sulfoxides and sulfones by conventional oxidation with m-chloroperoxybenzoic acid (MCPBA) is reported. The effects of alpha-(1--{\textgreater}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\% (IC(50)), measured via the MTT assay, ranged from 6.4 to 38.3 microg/mL. The effect of alpha-(1--{\textgreater}4)-3'-deoxythiodisaccharide derivatives were most profound on human pancreatic epithelial carcinoma (PANC-1) cells with compounds 8 and 9 having IC(50) values of 6.4 microg/mL and 8.2 microg/mL, respectively. Sulfone derivatives 16 and 17 also had pronounced effects on PANC-1 cell viability (IC(50)=10.2 microg/mL and 9.6 microg/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.},
	language = {eng},
	number = {1},
	journal = {Carbohydrate Research},
	author = {Witczak, Zbigniew J. and Kaplon, Peter and Dey, P. Markus},
	month = jan,
	year = {2003},
	pmid = {12504376},
	keywords = {Animals, Antineoplastic Agents, Carbohydrates, Cell Division, Cell Survival, Humans, Inhibitory Concentration 50, Mice, Structure-Activity Relationship, Sulfhydryl Compounds, Sulfones, Sulfoxides, Tumor Cells, Cultured},
	pages = {11--18},
}

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