Adsorption properties of the penicillin derivative DTPA on gold substrates

Laurent Dreesen, Cedric Volcke, Yannick Sartenaer, Paul Thiry, André Peremans, Jérôme Grugier, Jacqueline Marchand-Brynaert, Alain Brans, Stana Grubisic, Bernard Joris, Christophe Silien

Research output: Contribution to journalArticle

Abstract

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.
Original languageEnglish
Pages (from-to)1071-1076
Number of pages6
JournalChemPhysChem
Volume8
Publication statusPublished - 2007

Keywords

  • antibiotics · chemisorption · immobilization · monolayers · synthetic methods

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    Dreesen, L., Volcke, C., Sartenaer, Y., Thiry, P., Peremans, A., Grugier, J., Marchand-Brynaert, J., Brans, A., Grubisic, S., Joris, B., & Silien, C. (2007). Adsorption properties of the penicillin derivative DTPA on gold substrates. ChemPhysChem, 8, 1071-1076.