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Thioureido N-acetyllactosamine derivatives as potent galectin-7 and 9N inhibitors

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Author

Summary, in English

Derivatives of N-acetyllactosamine carrying structurally diverse thioureido groups at galactose C3 were prepared from a C3'-azido N-acetyllactosamine derivative in a three-step reaction sequence involving azide reduction and isothiocyanate formation by thiophosgene treatment of the C3-amine, followed by reaction of the isothiocyanate with a panel of amines. Evaluation of the N-acetyllactosamine thioureas as inhibitors against galectins-1, 3, 7, 8N (N-terminal domain), and 9N (N-terminal domain) revealed thiourea-mediated affinity enhancements for galectins-1, 3, 7, and 9N. In particular, good inhibitors were discovered against galectin-7 and 9N (K-d 23 and 47 mu M, respectively, for a 3-pyridylinethylthiourea derivative), which represents more than an order of magnitude affinity enhancement over the parent natural N-acetyllactosamine. (c) 2005 Elsevier Ltd. All rights reserved.

Publishing year

2006

Language

English

Pages

1215-1220

Publication/Series

Bioorganic & Medicinal Chemistry

Volume

14

Issue

4

Document type

Journal article

Publisher

Elsevier

Topic

  • Microbiology in the medical area
  • Immunology in the medical area

Keywords

  • N-acetyllactosamine
  • thiourea
  • galectin
  • inhibitor

Status

Published

ISBN/ISSN/Other

  • ISSN: 0968-0896