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Abstract:

Herein, we describe the design and synthesis of a novel family of hydrolytically stable glycoclusters bearing thiodigalactoside (TDG) analogues as recognition elements of β-galactoside binding lectins. The TDG analogue was synthesized by thioglycosylation of a 6-S-acetyl-α-d-glucosyl bromide with the isothiouronium salt of 2,3,4,6-tetra-O-acetyl-β-d-galactose. Further propargylation of the TDG analogue allowed the coupling to azido-functionalized oligosaccharide scaffolds through copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) under microwave activation. The final mono-, di-, and tetravalent ligands were resistant to enzymatic hydrolisis by Escherichia coli β-galactosidase. Binding affinities to peanut agglutinin and human galectin-3 were measured by isothermal titration calorimetry which showed Ka constants in the micromolar range as well as a multivalent effect. Monovalent ligand exhibited a binding affinity higher than that of thiodigalactoside. Docking studies performed with a model ligand on both β-galactoside binding lectins showed additional interactions between the triazole ring and lectin amino acid residues, suggesting a positive effect of this aromatic residue on the biological activity. © 2014 American Chemical Society.

Registro:

Documento: Artículo
Título:Design and synthesis of hydrolytically stable multivalent ligands bearing thiodigalactoside analogues for peanut lectin and human galectin-3 binding
Autor:Cagnoni, A.J.; Kovensky, J.; Uhrig, M.L.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, 1428 Buenos Aires, Argentina
Laboratoire de Glycochimie, des Antimicrobiens et des Agroressources (LG2A), CNRS FRE 3517, Université de Picardie Jules Verne, 33 rue Saint Leu, 80039 Amiens Cedex, France
Palabras clave:Amino acids; Binding energy; Bioactivity; Escherichia coli; Proteins; Scaffolds; Amino acid residues; Binding affinities; Copper(i) catalyzed azide alkyne cycloaddition (CuAAC); Isothermal titration calorimetry; Microwave activation; Multivalent effect; Multivalent ligands; Recognition element; Ligands; alkyne; ascorbic acid; azide; beta galactoside; bromine derivative; copper sulfate; cuprous ion; galactoside; galectin 3; ligand; oligosaccharide; peanut agglutinin; triphenylphosphine; galectin 3; galectin-3, human; glycoconjugate; lectin; ligand; thiodigalactoside; thioglycoside; acetylation; article; binding affinity; carbon nuclear magnetic resonance; cycloaddition; electrospray mass spectrometry; Escherichia coli; glycosylation; human; hydrogen bond; hydrolysis; isothermal titration calorimetry; microwave irradiation; molecular docking; molecular weight; nonhuman; nucleophilicity; peanut; protein binding; proton nuclear magnetic resonance; reaction time; stoichiometry; synthesis; thin layer chromatography; carbohydrate analysis; chemical structure; chemistry; conformation; molecular genetics; peanut; Arachis hypogaea; Carbohydrate Conformation; Carbohydrate Sequence; Galectin 3; Glycoconjugates; Humans; Hydrolysis; Lectins; Ligands; Models, Molecular; Molecular Sequence Data; Thiogalactosides
Año:2014
Volumen:79
Número:14
Página de inicio:6456
Página de fin:6467
DOI: http://dx.doi.org/10.1021/jo500883v
Título revista:Journal of Organic Chemistry
Título revista abreviado:J. Org. Chem.
ISSN:00223263
CODEN:JOCEA
CAS:ascorbic acid, 134-03-2, 15421-15-5, 50-81-7; azide, 12596-60-0, 14343-69-2; copper sulfate, 7758-98-7, 7758-99-8; galectin 3, 208128-56-7; triphenylphosphine, 603-35-0; Galectin 3; galectin-3, human; Glycoconjugates; Lectins; Ligands; thiodigalactoside; Thiogalactosides
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v79_n14_p6456_Cagnoni

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Citas:

---------- APA ----------
Cagnoni, A.J., Kovensky, J. & Uhrig, M.L. (2014) . Design and synthesis of hydrolytically stable multivalent ligands bearing thiodigalactoside analogues for peanut lectin and human galectin-3 binding. Journal of Organic Chemistry, 79(14), 6456-6467.
http://dx.doi.org/10.1021/jo500883v
---------- CHICAGO ----------
Cagnoni, A.J., Kovensky, J., Uhrig, M.L. "Design and synthesis of hydrolytically stable multivalent ligands bearing thiodigalactoside analogues for peanut lectin and human galectin-3 binding" . Journal of Organic Chemistry 79, no. 14 (2014) : 6456-6467.
http://dx.doi.org/10.1021/jo500883v
---------- MLA ----------
Cagnoni, A.J., Kovensky, J., Uhrig, M.L. "Design and synthesis of hydrolytically stable multivalent ligands bearing thiodigalactoside analogues for peanut lectin and human galectin-3 binding" . Journal of Organic Chemistry, vol. 79, no. 14, 2014, pp. 6456-6467.
http://dx.doi.org/10.1021/jo500883v
---------- VANCOUVER ----------
Cagnoni, A.J., Kovensky, J., Uhrig, M.L. Design and synthesis of hydrolytically stable multivalent ligands bearing thiodigalactoside analogues for peanut lectin and human galectin-3 binding. J. Org. Chem. 2014;79(14):6456-6467.
http://dx.doi.org/10.1021/jo500883v