Selection of the biological activity of DNJ neoglycoconjugates through click length variation of the side chain

被引：33

作者：

Ardes-Guisot, Nicolas ^{[2
,3
]}

Alonzi, Dominic S. ^{[4
]}

Reinkensmeier, Gabriele ^{[4
]}

Butters, Terry D. ^{[4
]}

Norez, Caroline ^{[5
]}

Becq, Frederic ^{[5
]}

Shimada, Yousuke ^{[6
]}

Nakagawa, Shinpei ^{[6
]}

Kato, Atsushi ^{[6
]}

Bleriot, Yves ^{[1
,7
]}

Sollogoub, Matthieu

Vauzeilles, Boris ^{[2
,3
]}

机构：

[1] Univ Poitiers, Lab Synth & React Subst Nat, CNRS, UMR 6514, F-86022 Poitiers, France

[2] CNRS, F-91405 Orsay, France

[3] Univ Paris Sud, ICMMO, UMR 8182, F-91405 Orsay, France

[4] Univ Oxford, Glycobiol Inst, Oxford OX1 3QU, England

[5] Univ Poitiers, CNRS, Inst Physiol & Biol Cellulaires, F-86022 Poitiers, France

[6] Toyama Univ, Dept Hosp Pharm, Toyama 9300194, Japan

[7] Univ Paris 06, UPMC, Inst Parisien Chim Mol, CNRS,UMR 7201, F-75005 Paris, France

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 15期

关键词：

HEPATITIS-C-VIRUS; CYSTIC-FIBROSIS; PHARMACOLOGICAL CHAPERONES; GAUCHER-DISEASE; GLUCOSYLCERAMIDE SYNTHASE; GLYCOSIDASE INHIBITORS; REPLACEMENT THERAPY; DEFECTIVE ENZYME; IMINO SUGARS; GLUCOSIDASE;

D O I：

10.1039/c1ob05119a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of neoglycoconjugates derived from deoxynojirimycin has been prepared by click connection with functionalised adamantanes. They have been assayed as glycosidase inhibitors, as inhibitors of the glycoenzymes relevant to the treatment of Gaucher disease, as well as correctors of the defective ion-transport protein involved in cystic fibrosis. We have demonstrated that it is possible to selectively either strongly inhibit ER-alpha-glucosidases and ceramide glucosyltransferase or restore the activity of CFTR in CF-KM4 cells by varying the length of the alkyl chain linking DNJ and adamantane.

引用

页码：5373 / 5388

页数：16

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