Are enzymes sensitive to the multivalent effect? Emerging evidence with glycosidases

被引：54

作者：

Matassini, Camilla ^{[1
]}

Parmeggiani, Camilla ^{[1
,2
,3
]}

Cardona, Francesca ^{[1
]}

Goti, Andrea ^{[1
]}

机构：

[1] Univ Florence, Dipartimento Chim Ugo Schiff, Via Lastruccia 3-13, I-50019 Sesto Fiorentino, Italy

[2] UOS Sesto Fiorentino, CNR INO, Via Nello Carrara 1, I-50019 Sesto Fiorentino, Italy

[3] LENS, Via Nello Carrara 1, I-50019 Sesto Fiorentino, Italy

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 49期

基金：

欧洲研究理事会;

关键词：

Multivalency; Glycosidases; Inhibitors; Iminosugars; Synthesis; IMINOSUGAR CLICK CLUSTERS; CARBOHYDRATE-PROCESSING ENZYMES; LYSOSOMAL STORAGE DISORDERS; ALPHA-L-FUCOSIDASE; PHARMACOLOGICAL CHAPERONES; REPLACEMENT THERAPY; GAUCHER-DISEASE; INHIBITION; BALLS; ARCHITECTURES;

D O I：

10.1016/j.tetlet.2016.10.080

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The multivalent effect in glycosidase inhibition is rapidly emerging as a hot topic of the research. In the last five years, several iminosugar-based inhibitors showed remarkable multivalent effects towards specific glycosidases, thus demonstrating that the concept of multivalency goes far beyond the interaction among protein receptors, as lectins, and carbohydrates and can be involved also for enzymes bearing a single active site. This critical overview aims to illustrate and discuss both cases of glycosidases prone to accept inhibitors with a multivalent presentation of the bioactive molecule as well as enzymes displaying a controversial behavior. (C) 2016 Elsevier Ltd. All rights reserved.

引用

收藏

页码：5407 / 5415

页数：9

相关论文

共 54 条

[1]

[Anonymous], 2007, IMINOSUGARS SYNTHESI

[2] Glycosidase inhibitors: update and perspectives on practical use [J].

Asano, N .

GLYCOBIOLOGY, 2003, 13 (10) :93R-104R

[3] Iminosugar-based glycopolypeptides: glycosidase inhibition with bioinspired glycoprotein analogue micellar self-assemblies [J].

Bonduelle, Colin ;

Huang, Jin ;

Mena-Barragan, Teresa ;

Ortiz Mellet, Carmen ;

Decroocq, Camille ;

Etame, Emile ;

Heise, Andreas ;

Compain, Philippe ;

Lecommandoux, Sebastien .

CHEMICAL COMMUNICATIONS, 2014, 50 (25) :3350-3352

[4] Enzyme replacement therapy for alpha-mannosidosis: 12 months follow-up of a single centre, randomised, multiple dose study [J].

Borgwardt, L. ;

Dali, C. I. ;

Fogh, J. ;

Mansson, J. E. ;

Olsen, K. J. ;

Beck, H. C. ;

Nielsen, K. G. ;

Nielsen, L. H. ;

Olsen, S. O. E. ;

Riise Stensland, H. M. F. ;

Nilssen, O. ;

Wibrand, F. ;

Thuesen, A. M. ;

Pearl, T. ;

Haugsted, U. ;

Saftig, P. ;

Blanz, J. ;

Jones, S. A. ;

Tylki-Szymanska, A. ;

Guffon-Fouiloux, N. ;

Beck, M. ;

Lund, A. M. .

JOURNAL OF INHERITED METABOLIC DISEASE, 2013, 36 (06) :1015-1024

[5] Pharmacological Chaperones as Therapeutics for Lysosomal Storage Diseases [J].

Boyd, Robert E. ;

Lee, Gary ;

Rybczynski, Philip ;

Benjamin, Elfrida R. ;

Khanna, Richie ;

Wustman, Brandon A. ;

Valenzano, Kenneth J. .

JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (07) :2705-2725

[6] Polymeric Iminosugars Improve the Activity of Carbohydrate-Processing Enzymes [J].

Brissonnet, Yoan ;

Ladeveze, Simon ;

Teze, David ;

Fabre, Emeline ;

Deniaud, David ;

Daligault, Franck ;

Tellier, Charles ;

Sestak, Sergej ;

Remaud-Simeon, Magali ;

Potocki-Veronese, Gabrielle ;

Gouin, Sebastien G. .

BIOCONJUGATE CHEMISTRY, 2015, 26 (04) :766-772

[7] Topological Effects and Binding Modes Operating with Multivalent Iminosugar-Based Glycoclusters and Mannosidases [J].

Brissonnet, Yoan ;

Ortiz Mellet, Carmen ;

Morandat, Sandrine ;

Garcia Moreno, M. Isabel ;

Deniaud, David ;

Matthews, Susan E. ;

Vidal, Sebastien ;

Sestak, Sergej ;

El Kirat, Karim ;

Gouin, Sebastien G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (49) :18427-18435

[8]

Choi S.K., 2004, SYNTHETIC MULTIVALEN

[9] Searching for Glycomimetics That Target Protein Misfolding in Rare Diseases: Successes, Failures, and Unexpected Progress Made in Organic Synthesis [J].

Compain, Philippe .

SYNLETT, 2014, 25 (09) :1215-1240

[10] The Multivalent Effect in Glycosidase Inhibition: A New, Rapidly Emerging Topic in Glycoscience [J].

Compain, Philippe ;

Bodlenner, Anne .

CHEMBIOCHEM, 2014, 15 (09) :1239-1251

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