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

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Abstract

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.

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Ämnesklassifikation (UKÄ) – OBLIGATORISK

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Nyckelord

Originalspråkengelska
Sidor (från-till)5283-5299
TidskriftBioorganic & Medicinal Chemistry
Volym15
Utgivningsnummer15
StatusPublished - 2007
PublikationskategoriForskning
Peer review utfördJa