Strong inhibition of cholera toxin by multivalent GM1 derivatives

被引：79

作者：

Pukin, Aliaksei V.

Branderhorst, Hilbert M.

Sisu, Cristina

Weijers, Carel A. G. M.

Gilbert, Michel

Liskamp, Rob M. J.

Visser, Gerben M.

Zuilhof, Han

Pieters, Roland J.

机构：

[1] Wageningen Univ, Organ Chem Lab, NL-6703 HB Wageningen, Netherlands

[2] Univ Utrecht, Utrecht Inst Pharmaceut Sci, Dept Med Chem & Chem Biol, NL-3508 TB Utrecht, Netherlands

[3] Natl Res Council Canada, Inst Biol Sci, Ottawa, ON K1A 0R6, Canada

来源：

CHEMBIOCHEM | 2007年 / 8卷 / 13期

关键词：

dendrimers; glycoconjugates; ligand design; oligosaccharides;

D O I：

10.1002/cbic.200700266

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

(Chemical Equation Presented) Sticky fingers. The optimal ligand for the cholera toxin (CT), GM1-oligosaccharide (GM1os), was linked to dendritic structures that contained long spacer arms by using highly efficient click" chemistry coupling. In the inhibition studies very large multivalency effects were observed; the best structure was an unprecedented 380 000-fold more potent ligand for the toxin than a monovalent GM1os derivative. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA."

引用

页码：1500 / 1503

页数：4

共 41 条

[1] Ganglioside-liposome immunoassay for the ultrasensitive detection of cholera toxin
Ahn-Yoon, S
DeCory, TR
Baeumner, AJ
Durst, RA
[J]. ANALYTICAL CHEMISTRY, 2003, 75 (10) : 2256 - 2261
[2] A synthetic divalent cholera toxin glycocalix[4]arene ligand having higher affinity than natural GM1 oligosaccharide
Arosio, D
Fontanella, M
Baldini, L
Mauri, L
Bernardi, A
Casnati, A
Sansone, F
Ungaro, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) : 3660 - 3661
[3] Synthesis and cholera toxin binding properties of multivalent GM1 mimics
Arosio, D
Vrasidas, I
Valentini, P
Liskamp, RMJ
Pieters, RJ
Bernardi, A
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (14) : 2113 - 2124
[4] Adhesion inhibition of F1C-fimbriated Escherichia coli and Pseudomonas aeruginosa PAK and PAO by multivalent carbohydrate ligands
Autar, R
Khan, AS
Schad, M
Hacker, J
Liskamp, RMJ
Pieters, RJ
[J]. CHEMBIOCHEM, 2003, 4 (12) : 1317 - 1325
[5] Chemical glycobiology
Bertozzi, CR
Kiessling, LL
[J]. SCIENCE, 2001, 291 (5512) : 2357 - 2364
[6] CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective
Bock, VD
Hiemstra, H
van Maarseveen, JH
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) : 51 - 68
[7] Brouwer AJ, 2001, EUR J ORG CHEM, V2001, P1903
[8] Bacteria as potential tools in bioterrorism, with an emphasis on bacterial toxins
Clarke, SC
[J]. BRITISH JOURNAL OF BIOMEDICAL SCIENCE, 2005, 62 (01) : 40 - 46
[9] Clicking functionality onto electrode surfaces
Collman, JP
Devaraj, NK
Chidsey, CED
[J]. LANGMUIR, 2004, 20 (04) : 1051 - 1053
[10] Characterization of the binding of cholera toxin to ganglioside GM1 immobilized onto microtitre plates
Dawson, RM
[J]. JOURNAL OF APPLIED TOXICOLOGY, 2005, 25 (01) : 30 - 38

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