Multimerization of DAB-1 onto Au GNPs affords new potent and selective N-acetylgalactosamine-6-sulfatase (GALNS) inhibitors

Gold glyconanoparticles (Au GNPs) decorated with the natural iminosugar DAB-1 at different densities are reported. These new multivalent iminosugar architectures strongly and selectively inhibit N-acetylgalactosamine-6-sulfatase (GALNS), whose deficiency is connected to the lysosomal storage disease...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2018-11, Vol.16 (44), p.8604-8612
Main Authors: Matassini, C, Vanni, C, Goti, A, Morrone, A, Marradi, M, Cardona, F
Format: Article
Language:English
Subjects:
Gold
N-Acetylgalactosamine
N-Acetylgalactosamine-6-sulfatase
Nanoparticles
NMR
Nuclear magnetic resonance
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Summary:Gold glyconanoparticles (Au GNPs) decorated with the natural iminosugar DAB-1 at different densities are reported. These new multivalent iminosugar architectures strongly and selectively inhibit N-acetylgalactosamine-6-sulfatase (GALNS), whose deficiency is connected to the lysosomal storage disease Morquio A. The combination of the dendrimeric technique with the synthetic strategy employed for Au GNP preparation allowed the enhancement of the multivalent presentation of the iminosugar onto the surface of gold nanoparticles, which resulted in the best GALNS inhibitor reported to date (IC50 = 520 nM).
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob02587h