Article (Scientific journals)
Discovery of novel lipophilic inhibitors of OXA-10 enzyme (class D beta-lactamase) by screening amino analogs and homologs of citrate and isocitrate.
Beck, Joséphine; Vercheval, Lionel; Bebrone, Carine et al.
2009In Bioorganic and Medicinal Chemistry Letters, 19, p. 3593-7
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Abstract :
[en] Aminocitrate (and homolog) derivatives have been prepared by bis-alkylation of glycinate Schiff bases with bromoacetates (and ethyl acrylate), followed by N-acylation and esters (partial or complete) deprotection. Aminoisocitrate was similarly obtained by mono-alkylation with diethyl fumarate. Evaluation against representative beta-lactamases revealed that the free acid derivatives are modest inhibitors of class A enzymes, whilst their benzyl esters showed a good inhibition of OXA-10 (class D enzyme). A docking experiment featured hydrophobic interactions in the active site.
Disciplines :
Biochemistry, biophysics & molecular biology
Author, co-author :
Beck, Joséphine;  Université Catholique de Louvain - UCL > Unité de chimie organique et médicinale
Vercheval, Lionel ;  Université de Liège - ULiège > Doct. sc. (bioch., bioch. mol.&cell., bioinf.&mod.-Bologne)
Bebrone, Carine ;  Université de Liège - ULiège > Centre d'ingénierie des protéines
Herteg-Fernea, Adriana;  Université de Liège - ULiège > Centre d'Ingénierie des Protéines
Lassaux, Patricia ;  Université de Liège - ULiège > Doct. sc. (bioch., bioch. mol.&cell., bioinf.&mod.-Bologne)
Marchand-Brynaert, Jacqueline;  Université Catholique de Louvain - UCL > Unité de chimie organique et médicinale
Language :
English
Title :
Discovery of novel lipophilic inhibitors of OXA-10 enzyme (class D beta-lactamase) by screening amino analogs and homologs of citrate and isocitrate.
Publication date :
01 July 2009
Journal title :
Bioorganic and Medicinal Chemistry Letters
ISSN :
0960-894X
eISSN :
1464-3405
Publisher :
Elsevier Science, Oxford, United Kingdom
Volume :
19
Pages :
3593-7
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE]
Available on ORBi :
since 21 September 2009

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