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

Mårten Jacobsson; Katrin Mani; Ulf Ellervik

doi:10.1016/j.bmc.2007.05.008

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

Mårten Jacobsson, Katrin Mani, Ulf Ellervik

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	5283-5299
Journal	Bioorganic & Medicinal Chemistry
Volume	15
Issue number	15
DOIs	https://doi.org/10.1016/j.bmc.2007.05.008
Publication status	Published - 2007

Bibliographical note

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)

Subject classification (UKÄ)

Medicinal Chemistry

Free keywords

Disulfides
Xylose
Glycosaminoglycan
Thio-β-d-xylopyranoside
Thioether

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10.1016/j.bmc.2007.05.008

Cite this

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title = "Effects of oxygen-sulfur substitution on glycosaminoglycan-priming naphthoxylosides.",

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.",

keywords = "Disulfides, Xylose, Glycosaminoglycan, Thio-β-d-xylopyranoside, Thioether",

author = "M{\aa}rten Jacobsson and Katrin Mani and Ulf Ellervik",

note = "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)",

year = "2007",

doi = "10.1016/j.bmc.2007.05.008",

language = "English",

volume = "15",

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journal = "Bioorganic & Medicinal Chemistry",

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T1 - Effects of oxygen-sulfur substitution on glycosaminoglycan-priming naphthoxylosides.

AU - Jacobsson, Mårten

AU - Mani, Katrin

AU - Ellervik, Ulf

N1 - 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)

PY - 2007

Y1 - 2007

N2 - 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.

AB - 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.

KW - Disulfides

KW - Xylose

KW - Glycosaminoglycan

KW - Thio-β-d-xylopyranoside

KW - Thioether

U2 - 10.1016/j.bmc.2007.05.008

DO - 10.1016/j.bmc.2007.05.008

M3 - Article

SN - 0968-0896

VL - 15

SP - 5283

EP - 5299

JO - Bioorganic & Medicinal Chemistry

JF - Bioorganic & Medicinal Chemistry

IS - 15

ER -

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

Abstract

Bibliographical note

Subject classification (UKÄ)

Free keywords

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