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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/647557
- author
- Jacobsson, Mårten
LU
; Mani, Katrin
LU
and Ellervik, Ulf
LU
- organization
- publishing date
- 2007
- 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
- additional info
- The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240), Glycobiology (013212006)
- id
- 3d5ef0d4-ee08-471d-92de-9c1be24af47e (old id 647557)
- date added to LUP
- 2016-04-01 11:42:45
- date last changed
- 2023-09-01 04:20:04
@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}},
keywords = {{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}},
doi = {{10.1016/j.bmc.2007.05.008}},
volume = {{15}},
year = {{2007}},
}