c14-hsl

Δ7(Z)-C14-HSL (Compound 12), an immunosuppressive agent, inhibits the proliferation of mouse splenic cells, exhibiting an IC 50 of 17 μM. It holds promise for exploring its role as a molecular mechanism in TNF-R-driven immune diseases, including autoimmune disorders like psoriasis, rheumatoid arthritis, and type 1 diabetes [1].

N-tetradecanoyl-L-homoserine lactone is a long-chain N-acyl homoserine lactone (AHL) and bacterial quorum sensing signal molecule that promotes diatom growth and upregulates genes involved in intracellular signalling.

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. Controlling bacterial infections by quenching their quorum sensing systems is a promising field of study. The expression of specific target genes, such as transcriptional regulators belonging to the LuxIR family of proteins, is coordinated by the synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-3-oxo-tetradecanoyl-L-homoserine lactone (3-oxo-C14-HSL) is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria.[1] [2] [3] It appears later than shorter acyl chain AHLs in developing biofilms [4] and, like other long chain 3-oxo-AHLs, stimulates the production of putisolvin, [5] which in turn, inhibits biofilm formation.

Quorum sensing is a regulatory process used by bacteria for controlling gene expression in response to increasing cell density. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. Coordinated gene expression is achieved by the production, release, and detection of small diffusible signal molecules called autoinducers. The N-acylated homoserine lactones (AHLs) comprise one such class of autoinducers, each of which generally consists of a fatty acid coupled with homoserine lactone (HSL). AHLs vary in acyl group length (C4-C18), in the substitution of C3 (hydrogen, hydroxyl, or oxo group) and in the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signal specificity through the affinity of transcriptional regulators of the LuxR family. C14:1-δ9-cis-(L)-HSL is a long-chain AHL that functions as a signaling molecule in the quorum sensing of A. vitis. Regulating bacterial quorum sensing signaling can be used to inhibit pathogenesis and thus, represents a new approach to antimicrobial therpy in the treatment of infectious diseases.