Multimeric Deoxynojirimycin Derivatives to Investigate Glycosidases Inhibition Exploiting Gold Glyconanoparticles

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Multimeric Deoxynojirimycin Derivatives to Investigate Glycosidases Inhibition Exploiting Gold Glyconanoparticles

Costanza Vanni 1 , Camilla Matassini 1 , Andrea Goti 1 , Francesca Cardona 1 , Marco Marradi 1 , Anne Bodlenner 2 , Philippe Compain 2

1 University of Florence, Sesto Fiorentino (FI), Italy, 2 Université de Strasbourg , Strasbourg, France

Gold glyconanoparticles (Au-GNPs) are multivalent tools based on self-assembled monolayers (SAMs) of thiol-ending glycoconjugates grafted onto gold nanoparticles by means of Au–S bonds. These hybrid multivalent systems show significant water solubility together with a good cell permeability, which is essential for therapeutic applications.[1] Multivalent architectures bearing several bioactive units assembled onto a common scaffold showed to be more effective in improving the binding affinity to different kinds of carbohydrate-binding proteins, including enzymes, compared to their parent monovalent counterparts.[2] This is defined as the “Multivalent Effect (MVE)”, and was investigated and observed to be successful also in glycosidase inhibition. [3] Iminosugars are glycomimetics with a nitrogen atom replacing the ring oxygen of sugars and are widely known to inhibit glycosidases.[4] We recently prepared Au-GNPs decorated with pyrrolidine iminosugars, which were able to inhibit enzymes related to metabolic diseases. [5] By following a similar strategy, we now report the preparation and characterization of Au-GNPs decorated with ligands based on deoxynojirimycin (DNJ, Figure 1), a widely investigated iminosugar that has already shown excellent enhancement activities towards commercially available jack-bean α-mannosidase. Preliminary biological evaluation of these new multivalent architectures will be also presented.

Figure 1: Representation of gold glyconanoparticles decorated with deoxynojirimycin (DNJ) derivatives.

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