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Issue 16, 2019
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Hybrid ligands with calixarene and thiodigalactoside groups: galectin binding and cytotoxicity

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Abstract

Galectins have diverse functions and are involved in many biological processes because of their complex intra- and extracellular activities. Selective and potent inhibitors for galectins will be valuable tools to investigate the biological functions of these proteins. Therefore, we describe here the synthesis of galectin inhibitors with a potential “chelate effect”. These compounds are designed to bind to two different binding sites on galectins simultaneously. In this paper a series of asymmetric “hybrid” compounds are prepared, which combine two galectin ligands (1) a substituted thiodigalactoside derivative and (2) an antagonist calixarene-based therapeutic agent. NMR spectroscopy was used to evaluate the interactions of these compounds with Galectin-1 and -3. In addition, cellular experiments were conducted to compare the cytotoxic effects of the hybrids with those of a calixarene derivative. While only the thiodigalactoside part of the hybrids showed strong binding, the calixarene part was responsible for observed cytoxoxicity effects, suggesting that the calixarene moiety may also be addressing a non-galectin target.

Graphical abstract: Hybrid ligands with calixarene and thiodigalactoside groups: galectin binding and cytotoxicity

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Publication details

The article was received on 26 Jun 2019, accepted on 08 Jul 2019 and first published on 12 Jul 2019


Article type: Research Article
DOI: 10.1039/C9QO00810A
Org. Chem. Front., 2019,6, 2981-2990

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    Hybrid ligands with calixarene and thiodigalactoside groups: galectin binding and cytotoxicity

    H. Zhang, H. Ippel, M. C. Miller, T. J. Wong, A. W. Griffioen, K. H. Mayo and R. J. Pieters, Org. Chem. Front., 2019, 6, 2981
    DOI: 10.1039/C9QO00810A

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