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Title: Design, synthesis and the effect of 1,2,3-triazole sialylmimetic neoglycoconjugates on Trypanosoma cruzi and its cell surface trans-sialidase
Authors: Campo, Vanessa L.
Sesti-Costa, Renata
Carneiro, Zumira A.
Silva, Joao S.
Schenkman, Sergio [UNIFESP]
Carvalho, Ivone
Universidade de São Paulo (USP)
Universidade Federal de São Paulo (UNIFESP)
Keywords: Triazole
Click chemistry
Trypanosoma cruzi
Issue Date: 1-Jan-2012
Publisher: Elsevier B.V.
Citation: Bioorganic & Medicinal Chemistry. Oxford: Pergamon-Elsevier B.V., v. 20, n. 1, p. 145-156, 2012.
Abstract: This work describes the synthesis of a series of sialylmimetic neoglycoconjugates represented by 1,4-disubstituted 1,2,3-triazole-sialic acid derivatives containing galactose modified at either C-1 or C-6 positions, glucose or gulose at C-3 position, and by the amino acid derivative 1,2,3-triazole fused threonine-3-O-galactose as potential TcTS inhibitors and anti-trypanosomal agents. This series was obtained by Cu(I)-catalysed azide-alkyne cycloaddition reaction ('click chemistry') between the azido-functionalized sugars 1-N(3)-Gal (commercial), 6-N(3)-Gal, 3-N(3)-Glc and 3-N(3)-Gul with the corresponding alkyne-based 2-propynyl-sialic acid, as well as by click chemistry reaction between the amino acid N(3)-ThrOBn with 3-O-propynyl-GalOMe. the 1,2,3-triazole linked sialic acid-6-O-galactose and the sialic acid-galactopyranoside showed high Trypanosoma cruzi trans-sialidase (TcTS) inhibitory activity at 1.0 mM (approx. 90%), whilst only the former displayed relevant trypanocidal activity (IC(50) 260 mu M). These results highlight the 1,2,3-triazole linked sialic acid-6-O-galactose as a prototype for further design of new neoglycoconjugates against Chagas' disease. (C) 2011 Elsevier B.V. All rights reserved.
ISSN: 0968-0896
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