[en] Despite the large number of articles and patents dealing with penicillin and other b-lactam antibiotics, there have been no reports about the self-assembly of such substances as monolayers on gold surfaces. The main reason stems from the high reactivity of the b-lactam ring, which hinders the development of molecules possessing this entity together with a metal-anchoring function. Herein, we present the synthesis of a novel molecule, 6-[(R,S)-5-(1,2-dithiolan-3-yl)pentanoyl-amino]-penicillanic acid, which combines the b-lactam ring and a metal-anchoring group. Using spectroscopic tools, we demonstrate the chemisorption of this compound on gold as self-assembled monolayers without any alteration of the penicillin pharmacophore and document its
reactivity towards a penicillin-binding protein, BlaR-CTD. Our work is a preliminary step towards the development of new biosensors and well-ordered protein arrays, both based on the high affinity of penicillin for penicillin-binding proteins.
Disciplines :
Physics
Author, co-author :
Dreesen, Laurent ; Université de Liège - ULiège > Département de physique > Biophotonique
Silien, Christophe
Volcke, Cédric
Sartenaer, Yannick
Thiry, Paul A.
Peremans, André
Grugier, Jérome
Marchand-Brynaert, Jacqueline
Brans, Alain ; Université de Liège - ULiège > Centre d'ingénierie des protéines - GIGA-Management : Plate-forme production protéines
Grubisic, Stana ; Université de Liège - ULiège > Services administratifs généraux > Protection et hygiène du travail (SUPHT)
Joris, Bernard ; Université de Liège - ULiège > Département des sciences de la vie > Physiologie et génétique bactériennes - Centre d'ingénierie des protéines
Language :
English
Title :
Adsorption Properties of the Penicillin Derivative DTPA on Gold Substrates
Publication date :
2007
Journal title :
Chemphyschem: A European Journal of Chemical Physics and Physical Chemistry
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