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

Jacobsson, Mårten LU ; Mani, Katrin LU and Ellervik, Ulf LU (2007) In Bioorganic & Medicinal Chemistry 15(15). p.5283-5299
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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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Disulfides, Xylose, Glycosaminoglycan, Thio-β-d-xylopyranoside, Thioether
in
Bioorganic & Medicinal Chemistry
volume
15
issue
15
pages
5283 - 5299
publisher
Elsevier
external identifiers
  • wos:000247714900024
  • scopus:34249979248
ISSN
0968-0896
DOI
10.1016/j.bmc.2007.05.008
language
English
LU publication?
yes
id
3d5ef0d4-ee08-471d-92de-9c1be24af47e (old id 647557)
date added to LUP
2007-07-13 14:28:04
date last changed
2017-09-24 03:30:16
@article{3d5ef0d4-ee08-471d-92de-9c1be24af47e,
  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.},
  author       = {Jacobsson, Mårten and Mani, Katrin and Ellervik, Ulf},
  issn         = {0968-0896},
  keyword      = {Disulfides,Xylose,Glycosaminoglycan,Thio-β-d-xylopyranoside,Thioether},
  language     = {eng},
  number       = {15},
  pages        = {5283--5299},
  publisher    = {Elsevier},
  series       = {Bioorganic & Medicinal Chemistry},
  title        = {Effects of oxygen-sulfur substitution on glycosaminoglycan-priming naphthoxylosides.},
  url          = {http://dx.doi.org/10.1016/j.bmc.2007.05.008},
  volume       = {15},
  year         = {2007},
}