Adsorption Properties of the Penicillin Derivative DTPA on Gold Substrates

• Published in: Chemphyschem Vol. 8; no. 7; pp. 1071 - 1076
• Main Authors: Dreesen, Laurent, Silien, Christophe, Volcke, Cédric, Sartenaer, Yannick, Thiry, Paul A., Peremans, André, Grugier, Jerome, Marchand-Brynaert, Jacqueline, Brans, Alain, Grubisic, Stana, Joris, Bernard
• Format: Journal Article Web Resource
• Language: English
• Published: Weinheim WILEY-VCH Verlag 14.05.2007; WILEY‐VCH Verlag; Wiley; Wiley-VCH Verlag Gmbh
• Subjects: Adsorption; antibiotics; Biological and medical sciences; chemisorption; Chemistry; Exact sciences and technology; Fundamental and applied biological sciences. Psychology; General and physical chemistry; Gold - chemistry; immobilization; Molecular biophysics; Molecular Structure; monolayers; Penicillanic Acid - analogs & derivatives; Penicillanic Acid - chemistry; Penicillin-Binding Proteins - metabolism; Physical, chemical, mathematical & earth Sciences; Physics; Physique; Physique, chimie, mathématiques & sciences de la terre; Spectrum Analysis; Surface physical chemistry; Surface properties. Adsorption; synthetic methods; X-Rays; Substrate; Chemisorption; Monolayer; Gold; Adsorption; Penicillin; Immobilization; Transition metal; antibiotics; monolayers, synthetic methods
• DOI: 10.1002/cphc.200700087
• ISSN: 1439-4235; 1439-7641

Despite the large number of articles and patents dealing with penicillin and other β‐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 β‐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 β‐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. Immobilized antibiotics: A penicillin derivative is synthesized with a sulfur‐containing terminal group, which allows it to anchor to metallic substrates. This molecule spontaneously forms self‐assembled monolayers on gold substrates (see picture) without alteration of the penicillin pharmacophore properties.