Thioureido N-acetyllactosamine derivatives as potent galectin-7 and 9N inhibitors
(2006) In Bioorganic & Medicinal Chemistry 14(4). p.1215-1220- Abstract
- 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)
- 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. (Less)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/419553
- author
- Salameh, Bader LU ; Sundin, Anders LU ; Leffler, Hakon LU and Nilsson, Ulf LU
- organization
- publishing date
- 2006
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- N-acetyllactosamine, thiourea, galectin, inhibitor
- in
- Bioorganic & Medicinal Chemistry
- volume
- 14
- issue
- 4
- pages
- 1215 - 1220
- publisher
- Elsevier
- external identifiers
-
- wos:000234909700036
- pmid:16242339
- scopus:30344486680
- pmid:16242339
- ISSN
- 0968-0896
- DOI
- 10.1016/j.bmc.2005.09.050
- 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: Division of Microbiology, Immunology and Glycobiology - MIG (013025200), Organic chemistry (S/LTH) (011001240)
- id
- ea4cabf8-25a8-4564-a55f-f64eb236e67f (old id 419553)
- date added to LUP
- 2016-04-01 11:59:00
- date last changed
- 2022-01-26 21:06:10
@article{ea4cabf8-25a8-4564-a55f-f64eb236e67f,
abstract = {{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.}},
author = {{Salameh, Bader and Sundin, Anders and Leffler, Hakon and Nilsson, Ulf}},
issn = {{0968-0896}},
keywords = {{N-acetyllactosamine; thiourea; galectin; inhibitor}},
language = {{eng}},
number = {{4}},
pages = {{1215--1220}},
publisher = {{Elsevier}},
series = {{Bioorganic & Medicinal Chemistry}},
title = {{Thioureido N-acetyllactosamine derivatives as potent galectin-7 and 9N inhibitors}},
url = {{http://dx.doi.org/10.1016/j.bmc.2005.09.050}},
doi = {{10.1016/j.bmc.2005.09.050}},
volume = {{14}},
year = {{2006}},
}