Discovery of potent inhibitors of PapG adhesins from uropathogenic Escherichia coli through synthesis and evaluation of galabiose derivatives

Jörgen Ohlsson; J Jass; BE Uhlin; J Kihlberg; Ulf Nilsson

doi:10.1002/1439-7633(20020802)3:8<772::AID-CBIC772>3.0.CO;2-8

Discovery of potent inhibitors of PapG adhesins from uropathogenic Escherichia coli through synthesis and evaluation of galabiose derivatives

Jörgen Ohlsson, J Jass, BE Uhlin, J Kihlberg, Ulf Nilsson

Centre for Analysis and Synthesis

Research output: Contribution to journal › Article › peer-review

Abstract

The synthesis of two galabioside (Golalpha1-4Gal) collections based on diversification at the O-1 and O-3' atoms is reported. The galabiosides were evaluated as inhibitors of hemagglutination of human erythrocytes by two strains of Escherichia coli that expressed the class I and class II PapG adhesins, respectively. The class I adhesin. was found to prefer aromatic substituents both at the O-1 and the O-3' position of the galabiose disaccharide. One galabioside, p-methoxyphenyl [3-O-(m-nitrobenzyl)-alpha-D-galacto-pyranosyl]-(1-4)-beta-D-galactopyro noside], had an IC50 value of 4.1 mum, which is the best inhibition of the class I adhesin to date.

Original language	English
Pages (from-to)	772-779
Journal	ChemBioChem
Volume	3
Issue number	8
DOIs	https://doi.org/10.1002/1439-7633(20020802)3:8<772::AID-CBIC772>3.0.CO;2-8
Publication status	Published - 2002

Bibliographical note

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

Subject classification (UKÄ)

Organic Chemistry

Free keywords

inhibitors
galabiose
carbohydrates
antibiotics
bacterial adhesin

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10.1002/1439-7633(20020802)3:8<772::AID-CBIC772>3.0.CO;2-8

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title = "Discovery of potent inhibitors of PapG adhesins from uropathogenic Escherichia coli through synthesis and evaluation of galabiose derivatives",

abstract = "The synthesis of two galabioside (Golalpha1-4Gal) collections based on diversification at the O-1 and O-3' atoms is reported. The galabiosides were evaluated as inhibitors of hemagglutination of human erythrocytes by two strains of Escherichia coli that expressed the class I and class II PapG adhesins, respectively. The class I adhesin. was found to prefer aromatic substituents both at the O-1 and the O-3' position of the galabiose disaccharide. One galabioside, p-methoxyphenyl [3-O-(m-nitrobenzyl)-alpha-D-galacto-pyranosyl]-(1-4)-beta-D-galactopyro noside], had an IC50 value of 4.1 mum, which is the best inhibition of the class I adhesin to date.",

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author = "J{\"o}rgen Ohlsson and J Jass and BE Uhlin and J Kihlberg and Ulf Nilsson",

note = "The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)",

year = "2002",

doi = "10.1002/1439-7633(20020802)3:8<772::AID-CBIC772>3.0.CO;2-8",

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T1 - Discovery of potent inhibitors of PapG adhesins from uropathogenic Escherichia coli through synthesis and evaluation of galabiose derivatives

AU - Ohlsson, Jörgen

AU - Jass, J

AU - Uhlin, BE

AU - Kihlberg, J

AU - Nilsson, Ulf

N1 - The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

PY - 2002

Y1 - 2002

N2 - The synthesis of two galabioside (Golalpha1-4Gal) collections based on diversification at the O-1 and O-3' atoms is reported. The galabiosides were evaluated as inhibitors of hemagglutination of human erythrocytes by two strains of Escherichia coli that expressed the class I and class II PapG adhesins, respectively. The class I adhesin. was found to prefer aromatic substituents both at the O-1 and the O-3' position of the galabiose disaccharide. One galabioside, p-methoxyphenyl [3-O-(m-nitrobenzyl)-alpha-D-galacto-pyranosyl]-(1-4)-beta-D-galactopyro noside], had an IC50 value of 4.1 mum, which is the best inhibition of the class I adhesin to date.

AB - The synthesis of two galabioside (Golalpha1-4Gal) collections based on diversification at the O-1 and O-3' atoms is reported. The galabiosides were evaluated as inhibitors of hemagglutination of human erythrocytes by two strains of Escherichia coli that expressed the class I and class II PapG adhesins, respectively. The class I adhesin. was found to prefer aromatic substituents both at the O-1 and the O-3' position of the galabiose disaccharide. One galabioside, p-methoxyphenyl [3-O-(m-nitrobenzyl)-alpha-D-galacto-pyranosyl]-(1-4)-beta-D-galactopyro noside], had an IC50 value of 4.1 mum, which is the best inhibition of the class I adhesin to date.

KW - inhibitors

KW - galabiose

KW - carbohydrates

KW - antibiotics

KW - bacterial adhesin

U2 - 10.1002/1439-7633(20020802)3:8<772::AID-CBIC772>3.0.CO;2-8

DO - 10.1002/1439-7633(20020802)3:8<772::AID-CBIC772>3.0.CO;2-8

M3 - Article

SN - 1439-4227

VL - 3

SP - 772

EP - 779

JO - ChemBioChem

JF - ChemBioChem

IS - 8

ER -

Discovery of potent inhibitors of PapG adhesins from uropathogenic Escherichia coli through synthesis and evaluation of galabiose derivatives

Abstract

Bibliographical note

Subject classification (UKÄ)

Free keywords

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