Aromatic heterocycle galectin-1 interactions for selective single-digit nM affinity ligands.

ABSTRACT: A series of 3-triazole-thiogalactosides and 3,3'-triazole-thiodigalactosides substituted with different five-membered heterocycles at the C-4 triazole position were found to have high selectivity for galectin-1. Initial studies on the 3-triazole-thiogalactosides indicated that five membered heterocycles in general gave increased affinity for galectin-1 and improved selectivity over galectin-3. The selectivity profile was similar for thiodigalactosides exemplified by 3,3' substituted thien-3-yltriazole and thiazol-2-yltriazole, both having single-digit nM galectin-1 affinity and almost 10-fold galectin-1 selectivity. The binding interactions of a thiodigalactoside based galectin-1 inhibitor with two thien-3-yltriazole moieties were studied with X-ray crystallography. One of the thiophene mo

SUBMITTER: Peterson K 

PROVIDER: S-EPMC9082524 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature