Synthesis of multivalent Streptococcus suis adhesion inhibitors by enzymatic cleavage of polygalacturonic acid and 'click' conjugation

被引：26

作者：

Branderhorst, Hilbert M. ^{[1
]}

Kooij, Raymond ^{[1
]}

Salminen, Annika ^{[2
]}

Jongeneel, Lieneke H. ^{[1
]}

Arnusch, Christopher J. ^{[1
]}

Liskamp, Rob M. J. ^{[1
]}

Finne, Jukka ^{[2
]}

Pieters, Roland J. ^{[1
]}

机构：

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

[2] Univ Turku, Dept Med Biochem & Mol Biol, FI-20520 Turku, Finland

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2008年 / 6卷 / 08期

关键词：

D O I：

10.1039/b800283e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A galabiose disaccharide building block was synthesized by an efficient pectinase cleavage of polygalacturonic acid and subsequent chemical functional group transformations. Besides the disaccharide, the corresponding trisaccharide was also obtained and modified. The compounds were subsequently conjugated to dendrimers with up to eight end groups using 'click' chemistry. The compounds were evaluated as inhibitors of adhesion of the pathogen Streptococcus suis in a hemagglutination assay and strong inhibition was observed for the tetra- and octavalent galabiose compound with MIC values in the low nanomolar range. The corresponding octavalent trisaccharide was a ca. 20-fold weaker inhibitor.

引用

页码：1425 / 1434

页数：10

共 28 条

[1] Novel multivalent mannose compounds and their inhibition of the adhesion of type 1 fimbriated uropathogenic E. coli [J].

Appeldoorn, CCM ;

Joosten, JAF ;

el Maate, FA ;

Dobrindt, U ;

Hacker, J ;

Liskamp, RMJ ;

Khan, AS ;

Pieters, RJ .

TETRAHEDRON-ASYMMETRY, 2005, 16 (02) :361-372

[2]

ARENDS JP, 1988, REV INFECT DIS, V10, P131

[3] Adhesion inhibition of F1C-fimbriated Escherichia coli and Pseudomonas aeruginosa PAK and PAO by multivalent carbohydrate ligands [J].

Autar, R ;

Khan, AS ;

Schad, M ;

Hacker, J ;

Liskamp, RMJ ;

Pieters, RJ .

CHEMBIOCHEM, 2003, 4 (12) :1317-1325

[4]

BOCK K, 1985, J BIOL CHEM, V260, P8545

[5]

Brouwer AJ, 2001, EUR J ORG CHEM, V2001, P1903

[6] Studies on the binding site of the galactose-specific agglutinin PA-IL from Pseudomonas aeruginosa [J].

Chen, CP ;

Song, SC ;

Gilboa-Garber, N ;

Chang, KSS ;

Wu, AM .

GLYCOBIOLOGY, 1998, 8 (01) :7-16

[7] 4-0-ALPHA-D-GALACTOPYRANOSYL-D-GALACTOSE - EFFICIENT SYNTHETIC ROUTES FROM POLYGALACTURONIC ACID [J].

DAHMEN, J ;

FREJD, T ;

LAVE, T ;

LINDH, F ;

MAGNUSSON, G ;

NOORI, G ;

PALSSON, K .

CARBOHYDRATE RESEARCH, 1983, 113 (02) :219-224

[8] Exploring and exploiting the therapeutic potential of glycoconjugates [J].

Doores, KJ ;

Gamblin, DP ;

Davis, BG .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (03) :656-665

[9] Large-scale preparation of α-D-(1→4)-oligogalacturonic acids from pectic acid [J].

Fan, HN ;

Liu, MZ ;

Lee, YC .

CANADIAN JOURNAL OF CHEMISTRY, 2002, 80 (08) :900-903

[10] PA-I AND PA-II LECTIN INTERACTIONS WITH THE ABO(H)-BLOOD AND P-BLOOD GROUP GLYCOSPHINGOLIPID ANTIGENS MAY CONTRIBUTE TO THE BROAD-SPECTRUM ADHERENCE OF PSEUDOMONAS-AERUGINOSA TO HUMAN TISSUES IN SECONDARY INFECTIONS [J].

GILBOAGARBER, N ;

SUDAKEVITZ, D ;

SHEFFI, M ;

SELA, R ;

LEVENE, C .

GLYCOCONJUGATE JOURNAL, 1994, 11 (05) :414-417

← 1 2 3 →