Quorum sensing (QS) plays a pivotal role in both pathogenic and symbiotic bacteria-host interactions. Processes regulated by quorum sensing include conjugation, antibiotic production, motility, and biofilm formation. Novel analogues of N-acyl homoserine lactones (AHLs) in which a halogen atom was introduced at the a-position of the carbonyl function of the acyl chain have been prepared and studied as quorum sensing modulators. The novel analogues involve a-chloro, a-bromo and a-iodo AHLs. The biological activity of the halogenated AHL analogues was evaluated which demonstrated a reduced activity in the Escherichia coli JB523 bioassay, with the a-iodo AHLs being the less active ones. However, most of the a-haloacylated analogues failed to exhibit a significant reduction of QS activity in an inhibition test. Since this decrease in QS activity is related to the bulkiness of the halo substituent, steric effects play an important role in the binding of AHLs with their target receptors.

Synthesis and biological evaluation of N-α-haloacylated homoserine lactones

245th National Meeting (2013)

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