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Adsorption Properties of the Penicillin Derivative DTPA on Gold Substrates
Author(s) -
Dreesen Laurent,
Silien Christophe,
Volcke Cédric,
Sartenaer Yannick,
Thiry Paul A.,
Peremans André,
Grugier Jerome,
MarchandBrynaert Jacqueline,
Brans Alain,
Grubisic Stana,
Joris Bernard
Publication year - 2007
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.200700087
Subject(s) - pharmacophore , penicillin , chemistry , monolayer , combinatorial chemistry , molecule , ring (chemistry) , penicillin binding proteins , reactivity (psychology) , lactam , stereochemistry , derivative (finance) , biosensor , metal , antibiotics , organic chemistry , biochemistry , medicine , alternative medicine , pathology , financial economics , economics
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.