Display options
Cite
Nierengarten JF, Schneider JP, Trinh TMN, et al. Giant Glycosidase Inhibitors: First- and Second-Generation Fullerodendrimers with a Dense Iminosugar Shell. Chemistry. 2018;24(10):2483-2492doi: 10.1002/chem.201705600.
Nierengarten, J. F., Schneider, J. P., Trinh, T. M. N., Joosten, A., Holler, M., Lepage, M. L., Bodlenner, A., García-Moreno, M. I., Ortiz Mellet, C., & Compain, P. (2018). Giant Glycosidase Inhibitors: First- and Second-Generation Fullerodendrimers with a Dense Iminosugar Shell. Chemistry (Weinheim an der Bergstrasse, Germany), 24(10), 2483-2492. https://doi.org/10.1002/chem.201705600
Nierengarten, Jean-François, et al. "Giant Glycosidase Inhibitors: First- and Second-Generation Fullerodendrimers with a Dense Iminosugar Shell." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 24,10 (2018): 2483-2492. doi: https://doi.org/10.1002/chem.201705600
Nierengarten JF, Schneider JP, Trinh TMN, Joosten A, Holler M, Lepage ML, Bodlenner A, García-Moreno MI, Ortiz Mellet C, Compain P. Giant Glycosidase Inhibitors: First- and Second-Generation Fullerodendrimers with a Dense Iminosugar Shell. Chemistry. 2018 Feb 16;24(10):2483-2492. doi: 10.1002/chem.201705600. Epub 2018 Jan 25. PMID: 29281149.
Copy Download .nbib Format: NLM
Share it on

Chemistry. 2018 Feb 16;24(10):2483-2492. doi: 10.1002/chem.201705600. Epub 2018 Jan 25.

Giant Glycosidase Inhibitors: First- and Second-Generation Fullerodendrimers with a Dense Iminosugar Shell.

Chemistry (Weinheim an der Bergstrasse, Germany)

Jean-François Nierengarten, Jérémy P Schneider, Thi Minh Nguyet Trinh, Antoine Joosten, Michel Holler, Mathieu L Lepage, Anne Bodlenner, M Isabel García-Moreno, Carmen Ortiz Mellet, Philippe Compain

Affiliations

  1. Laboratoire de Chimie des Matériaux Moléculaires, Université de Strasbourg et CNRS (UMR 7509), Ecole Européenne de Chimie, Polymères et Matériaux, 25 rue Becquerel, 67087, Strasbourg Cedex 2, France.
  2. Laboratoire de Synthèse Organique et Molécules Bioactives, Université de Strasbourg et CNRS (UMR 7509), Ecole Européenne de Chimie, Polymères et Matériaux, 25 rue Becquerel, 67087, Strasbourg Cedex 2, France.
  3. Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Profesor García González 1, 41012, Sevilla, Spain.

PMID: 29281149 DOI: 10.1002/chem.201705600

Abstract

The multivalent effect in glycosidase inhibition is a new topic in glycoscience that has emerged a few years ago, with the discovery of neoglycoclusters displaying strong binding enhancements over the corresponding monovalent inhibitor. Iminosugar-fullerene conjugates with high valencies have been prepared from iminosugar-terminated dendrons and a clickable fullerene hexa-adduct scaffold. The simultaneous grafting of twelve dendrons allows for a very fast dendritic growth thus limiting the number of synthetic steps required to prepare compounds with a high number of peripheral units. The grafting of first- and second-generation dendrons provided fullerodendrimers surrounded by 36 and 108 peripheral iminosugars, respectively. Inhibition studies have been carried out with a panel of glycosidases. In the particular case of Jack bean α-mannosidase, the 108-valent nanoconstruct displays inhibition in the nanomolar range and an additional binding enhancement of one order of magnitude when compared to the 36-valent analogues.

© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: dendrimers; fullerenes; glycosidase inhibition; iminosugars; multivalent effects

Publication Types