Effects of oxygen-sulfur substitution on glycosaminoglycan-priming naphthoxylosides
Mårten Jacobsson1, Katrin Mani, Ulf Ellervik
1Organic Chemistry, Lund University, Lund, Sweden.
Abstract:
Three series of sulfur-containing analogs to the selectively antiproliferative 2-(6-hydroxynaphthyl) beta-D-xylopyranoside were synthesized and their biological properties investigated. A short, general route to hydroxynaphthyl disulfides from dihydroxynaphthalenes was developed to utilize the disulfide bond as a sulfur-selective protecting group to enable the orthogonal protection of hydroxyls and thiols. The results indicate that hydrophobic, uncharged oxygen-sulfur substituted naphthoxylosides are taken up by cells and initiate priming of GAG chains to a greater extent compared to the oxygen analogs. No correlation between priming ability and antiproliferative activity was observed.
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