Imidazolines as non-classical bioisosteres of Nacyl homoserine lactones and Quorum sensing inhibitors
Abstract number: P1250
Bucio-Cano A., Montenegro-Sustaita M., Curiel-Quesada E., Reyes-Arellano A., Aparicio-Ozores G.
Objectives: Synthesis of six non classical N-acyl homoserin lactone bioisosters and evaluation of their inhibitory effects on quorum sensing in Chromobacterium violaceum and Serratia marcescens.
Methods and Results: Imidazolyl ethers were synthesized by alkylation of 4-hydroxibenzadehyde followed by cyclization with ethylenediamine. Imidazolyl amides were synthesized by reaction of 4-amino benzonitrile with organic acids followed by cyclization with ethylenediamine. Products were characterized by NMR and EM. Structures of synthesized bioisosters are shown in Figure 1.
Figure 1. 3a: R = OCH2(CH2)4CH3; 3b: R = OCH2(CH2)7CH3; 3c: R = NHCOCH2(CH2)3CH3; 3d: NHCOCH2(CH2)6CH3.
In order to study their effect on QS, test bioisoster was added to bacterial cultures at final 100 pM to 1 mM concentrations and cultures were incubated for 15 h. Growth was monitored at OD720 while violacein production was measured at 577nm. For prodigiosin synthesis, S. marcescens was incubated for 48 h and pigment was recorded at 540 nm.
Figure 1 shows specific violacein production in the presence of four of the bioisosters assayed.
|Session name:||Abstracts 20th European Congress of Clinical Microbiology and Infectious Diseases|
|Location:||Vienna, Austria, 10 - 13 April 2010|
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