Effects of oxygen-sulfur substitution on glycosaminoglycan-priming naphthoxylosides.
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.
Jacobsson
Mårten
M
Organic Chemistry, Lund University, Lund, Sweden.
Mani
Katrin
K
Ellervik
Ulf
U
D002460:Cell Line; D006025:Glycosaminoglycans / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013455:Sulfur / Q000737:chemistry*
D006025:Glycosaminoglycans; D006027:Glycosides; C010807:xylosides; D013455:Sulfur; D010100:Oxygen