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1H-1,2,3-triazol-1-yl thiodigalactoside derivatives as high affinity galectin-3 inhibitors. 2010

Bader A Salameh, and Ian Cumpstey, and Anders Sundin, and Hakon Leffler, and Ulf J Nilsson
Chemistry Department, The Hashemite University, PO Box 150459, Zarka 13115, Jordan.

Galactose C3-triazole derivatives were synthesized by Cu(I)-catalyzed cycloaddition between acetylenes and galactose C3-azido derivatives. Evaluation against galectin-3, 7, 8N (N-terminal) and 9N (N-terminal) revealed 1,4-disubstituted triazoles to be high-affinity inhibitors of galectin-3 with selectivity over galectin-7, 8N, and 9N. Conformational analysis of 1,4-di- and 1,4,5-tri-substituted galactose C3-triazoles suggested that a triazole C5-substituent interfered sterically with the galectin proteins, which explained their poor affinities compared to the corresponding 1,4-disubstituted triazoles. Introduction of two 1,4-disubstituted triazole moieties onto thiodigalactoside resulted in affinities down to 29 nM for galectin-3.

UI MeSH Term Description Entries
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D013862 Thiogalactosides Galactosides in which the oxygen atom linking the sugar and aglycone is replaced by a sulfur atom. Thiogalactopyranosides
D014230 Triazoles Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3. Triazole
D037502 Galectin 3 A multifunctional galactin initially discovered as a macrophage antigen that binds to IMMUNOGLOBULIN E, and as 29-35-kDa lectin that binds LAMININ. It is involved in a variety of biological events including interactions with galactose-containing glycoconjugates, cell proliferation, CELL DIFFERENTIATION, and APOPTOSIS. Mac-2 Antigen,CBP-30,CBP-35,CBP35,Carbohydrate-Binding Protein 35,Epsilon-Binding Protein,Galectin-3,HL-29,IgE Binding Protein,IgEBP,L-29 Lectin,L-31,L-34,L30 Lectin,LGALS3,Macrophage-2 Antigen,Antigen, Mac-2,Antigen, Macrophage-2,Binding Protein, IgE,Carbohydrate Binding Protein 35,Epsilon Binding Protein,L 29 Lectin,Mac 2 Antigen,Macrophage 2 Antigen,Protein, IgE Binding

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