Synthesis and biological evaluation of gem-diamine 1-N-iminosugars related to L-iduronic acid as inhibitors of heparan sulfate 2-O-sulfotransferase

Jillian R Brown; Yoshio Nishimura; Jeffrey D Esko

doi:10.1016/j.bmcl.2005.10.055

Synthesis and biological evaluation of gem-diamine 1-N-iminosugars related to L-iduronic acid as inhibitors of heparan sulfate 2-O-sulfotransferase

Bioorg Med Chem Lett. 2006 Feb;16(3):532-6. doi: 10.1016/j.bmcl.2005.10.055. Epub 2005 Nov 4.

Authors

Jillian R Brown¹, Yoshio Nishimura, Jeffrey D Esko

Affiliation

¹ Department of Cellular and Molecular Medicine, Glycobiology Research and Training Center, University of California-San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0687, USA.

PMID: 16275065
DOI: 10.1016/j.bmcl.2005.10.055

Abstract

A variety of gem-diamine 1-N-iminosugars related to L-iduronic acid were synthesized and evaluated as inhibitors of heparan sulfate uronyl 2-O-sulfotransferase using an in vitro enzyme assay. Two iminosugars containing guanidino groups acted as potent in vitro inhibitors of the enzyme.

Publication types

Evaluation Study
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Animals
Binding Sites
Diamines / chemistry*
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / pharmacology
Humans
Iduronic Acid / chemistry*
Imino Sugars / chemical synthesis*
Imino Sugars / pharmacology
Models, Chemical
Sulfotransferases / antagonists & inhibitors*

Substances

Diamines
Enzyme Inhibitors
Imino Sugars
Iduronic Acid
Sulfotransferases
heparan-sulfate 2-sulfotransferase

Grants and funding

CA 112278/CA/NCI NIH HHS/United States