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Probing Bacterial Uptake of Glycosylated Ciprofloxacin Conjugates
Author(s) -
Milner Stephen J.,
Carrick Christopher T.,
Kerr Kevin G.,
Snelling Anna M.,
Thomas Gavin H.,
DuhmeKlair AnneKathrin,
Routledge Anne
Publication year - 2014
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201300512
Subject(s) - dna gyrase , disaccharide , ciprofloxacin , chemistry , antimicrobial , monosaccharide , bacteria , biochemistry , in vivo , microbiology and biotechnology , antibiotics , escherichia coli , biology , organic chemistry , genetics , gene
Mono‐ and disaccharide‐functionalised conjugates of the fluoroquinolone antibiotic ciprofloxacin have been synthesised and used as chemical probes of the bacterial uptake of glycosylated ciprofloxacin. Their antimicrobial activities against a panel of clinically relevant bacteria were determined: the ability of these conjugates to inhibit their target DNA gyrase and to be transported into the bacteria was assessed by using in vivo and in vitro assays. The data suggest a lack of active uptake through sugar transporters and that although the addition of monosaccharides is compatible with the inhibition of DNA gyrase, the addition of a disaccharide results in a significant decrease in antimicrobial activity.