Design and evaluation of analogues of the bacterial cell-wall peptidoglycan motif L-Lys-D-Ala-D-Ala for use in a vancomycin biosensor.
Four small molecular receptors of vancomycin have been designed to make part of a novel biosensor device based on the FTIR-ATR detection: N-Boc (2a) or N-Ac (2b)-6-aminocaproyl-D-Ala-D-Ala and N-Boc (3a) or N-Ac (3b)-6-aminocaproyl-D-Ala-d-Ser. Using an original microbiological approach to assess the competition of compounds with the natural target of vancomycin in bacteria, EC(50) values of 6.3-8.0 x 10(-5)M (2a-b) and 7.1-9.3 x 10(-4)M (3a-b) were determined. Vancomycin:2b complex was characterized by MS.
Hernout
Olivier
O
Unité de Chimie organique et médicinale, Université catholique de Louvain, Bâtiment Lavoisier, Place L. Pasteur 1, B-1348 Louvain-la-Neuve, Belgium.
Berthoin
Karine
K
Delattre
Isabelle
I
Tulkens
Paul M
PM
Carryn
Stéphane
S
Marchand-Brynaert
Jacqueline
J
D001419:Bacteria / Q000737:chemistry*; D015374:Biosensing Techniques; D002473:Cell Wall / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D015195:Drug Design; D004353:Drug Evaluation, Preclinical; D010457:Peptidoglycan / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D014640:Vancomycin / Q000032:analysis*
D010457:Peptidoglycan; D014640:Vancomycin