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Effects of oxygen-sulfur substitution on glycosaminoglycan-priming naphthoxylosides.

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Author

Summary, in English

Three series of sulfur-containing analogs to the selectively antiproliferative 2-(6-hydroxynaphthyl) β-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.

Publishing year

2007

Language

English

Pages

5283-5299

Publication/Series

Bioorganic & Medicinal Chemistry

Volume

15

Issue

15

Document type

Journal article

Publisher

Elsevier

Topic

  • Medicinal Chemistry

Keywords

  • Disulfides
  • Xylose
  • Glycosaminoglycan
  • Thio-β-d-xylopyranoside
  • Thioether

Status

Published

Research group

  • Glycobiology

ISBN/ISSN/Other

  • ISSN: 0968-0896