Adsorption properties of the penicillin derivative DTPA on gold substrates.
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.
Dreesen
Laurent
L
Laboratoire de Spectroscopie Moléculaire de Surface, University of Namur rue de Bruxelles 61, 5000 Namur, Belgium. laurent.dreesen@fundp.ac.be
Silien
Christophe
C
Volcke
Cédric
C
Sartenaer
Yannick
Y
Thiry
Paul A
PA
Peremans
André
A
Grugier
Jerome
J
Marchand-Brynaert
Jacqueline
J
Brans
Alain
A
Grubisic
Stana
S
Joris
Bernard
B
D000327:Adsorption; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D010397:Penicillanic Acid / Q000031:analogs & derivatives* / Q000737:chemistry*; D046915:Penicillin-Binding Proteins / Q000378:metabolism; D013057:Spectrum Analysis; D014965:X-Rays
C522688:6-((R,S)-5-(1,2-dithiolan-3-yl)pentanoyl-amino)penicillanic acid; D046915:Penicillin-Binding Proteins; D006046:Gold; D010397:Penicillanic Acid