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

Fingerprint

penicillin
Lactams
Pentetic Acid
Gold
Penicillins
Penicillin-Binding Proteins
gold
Derivatives
Adsorption
adsorption
Substrates
Metals
Molecules
proteins
Self assembled monolayers
Chemisorption
Biosensors
Self assembly
reactivity
charge transfer devices

Keywords

  • antibiotics · chemisorption · immobilization · monolayers · synthetic methods

Cite this

Dreesen, L., Volcke, C., Sartenaer, Y., Thiry, P., Peremans, A., Grugier, J., ... Silien, C. (2007). Adsorption properties of the penicillin derivative DTPA on gold substrates. ChemPhysChem, 8, 1071-1076.
Dreesen, Laurent ; Volcke, Cedric ; Sartenaer, Yannick ; Thiry, Paul ; Peremans, André ; Grugier, Jérôme ; Marchand-Brynaert, Jacqueline ; Brans, Alain ; Grubisic, Stana ; Joris, Bernard ; Silien, Christophe. / Adsorption properties of the penicillin derivative DTPA on gold substrates. In: ChemPhysChem. 2007 ; Vol. 8. pp. 1071-1076.
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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, vol. 8, pp. 1071-1076.

Adsorption properties of the penicillin derivative DTPA on gold substrates. / Dreesen, Laurent; Volcke, Cedric; Sartenaer, Yannick; Thiry, Paul; Peremans, André; Grugier, Jérôme; Marchand-Brynaert, Jacqueline; Brans, Alain; Grubisic, Stana; Joris, Bernard; Silien, Christophe.

In: ChemPhysChem, Vol. 8, 2007, p. 1071-1076.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Adsorption properties of the penicillin derivative DTPA on gold substrates

AU - Dreesen, Laurent

AU - Volcke, Cedric

AU - Sartenaer, Yannick

AU - Thiry, Paul

AU - Peremans, André

AU - Grugier, Jérôme

AU - Marchand-Brynaert, Jacqueline

AU - Brans, Alain

AU - Grubisic, Stana

AU - Joris, Bernard

AU - Silien, Christophe

PY - 2007

Y1 - 2007

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AB - 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.

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JF - ChemPhysChem

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Dreesen L, Volcke C, Sartenaer Y, Thiry P, Peremans A, Grugier J et al. Adsorption properties of the penicillin derivative DTPA on gold substrates. ChemPhysChem. 2007;8:1071-1076.