Adsorption properties of the penicillin derivative DTPA on gold substrates. |
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Authors: | Laurent Dreesen Christophe Silien Cédric Volcke Yannick Sartenaer Paul A Thiry André Peremans Jerome Grugier Jacqueline Marchand-Brynaert Alain Brans Stana Grubisic Bernard Joris |
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Institution: | Laboratoire de Spectroscopie Moléculaire de Surface, University of Namur rue de Bruxelles 61, 5000 Namur, Belgium. laurent.dreesen@fundp.ac.be |
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Abstract: | Despite the large number of articles and patents dealing with penicillin and other beta-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 beta-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 beta-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. |
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