Biofilms pose a threat to public health. The National Institutes of Health estimate that biofilms are linked to between 65 and 80% of hospital-related infections. Biofilms are a complex network of bacterial cells contained within an extracellular matrix and are 10-1000 times more resistant to common antibiotic treatments. Biofilms utilize a form of intercellular communication known as quorum sensing to regulate many bacterial functions including the excretion of the extracellular matrix and dispersal of planktonic cells. Compounds known as diffusible signaling factors (DSF) regulate the formation/degradation of the extracellular matrix. One family of DSF molecules consists of a carboxylic acid headgroup, a C2-C3 cis alkene, and an alkyl tail. Cis-2-decenoic acid (C2DA) can disperse gram-positive and gram-negative bacteria derived biofilms. However, C2DA is susceptible to oxidative degradation and isomerization, which both lead to a loss of activity. 2-heptylcyclopropyl-1-carboxylic acid (2CP) avoids this degradation by substitution of the cis-alkene with a cyclopropyl group. 2CP is a chemically stabilized form of C2DA that retains antibiofilm activity. We have expanded our analysis of DSF analogs to include alkoxy substituted benzoic acids as mimics of the cis-α/β unsaturation in C2DA. To date a series of 12 alkoxy benzoic analogs have been developed. These analogs differ in position (ortho, meta, para), overall chain length, and chain branching. Additional modification of the carboxylic acid headgroup is also in progress. Antibiofilm activity of these novel diffusible signaling factors will be discussed.

Synthesis and quantitative analysis of diffusible signaling factors, for determination of structure activity relationships and structural stability

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ACS Fall 2022

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