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 = O–CH2–(CH2)4–CH3; 3b: R = O–CH2–(CH2)7–CH3; 3c: R = NH–CO–CH2–(CH2)3–CH3; 3d: NH–CO–CH2–(CH2)6–CH3.

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 Details

Date: 10/04/2010
Time: 00:00-00:00
Session name: Abstracts 20th European Congress of Clinical Microbiology and Infectious Diseases
Location: Vienna, Austria, 10 - 13 April 2010
Presentation type:
Back to top