Effects of oxygen-sulfur substitution on glycosaminoglycan-priming naphthoxylosides.
Författare
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.
Avdelning/ar
Publiceringsår
2007
Språk
Engelska
Sidor
5283-5299
Publikation/Tidskrift/Serie
Bioorganic & Medicinal Chemistry
Volym
15
Issue
15
Dokumenttyp
Artikel i tidskrift
Förlag
Elsevier
Ämne
- Medicinal Chemistry
Nyckelord
- Disulfides
- Xylose
- Glycosaminoglycan
- Thio-β-d-xylopyranoside
- Thioether
Status
Published
Forskningsgrupp
- Glycobiology
ISBN/ISSN/Övrigt
- ISSN: 0968-0896