168982-69-2

Basic information

• Product Name: 3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide
• Synonyms: 3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide;N-(3-oxododecanoyl)-L-homoserine lactone L-enantiomer;(S)-3-Oxo-N-(2-oxotetrahydrofuran-3-yl)dodecanamide
• CAS NO: 168982-69-2
• Molecular Formula: C₁₆H₂₇NO₄
• Molecular Weight: 297.392
• Mol File: 168982-69-2.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 519.4 °C at 760 mmHg
• Flash Point: 267.924 °C
• Appearance: /
• Density: 1.06
• Storage Temp.: -20°C
• Solubility: ≤20mg/ml in DMSO;20mg/ml in dimethyl formamide
• CAS DataBase Reference: 3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide(168982-69-2)
• EPA Substance Registry System: 3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide(168982-69-2)

Safety Data

• Hazardous Substances Data: 168982-69-2(Hazardous Substances Data)

Usage

Description

N-3-oxo-dodecanoyl-L-Homoserine lactone (3-oxo-C12-HSL) is a bacterial quorum-sensing signaling molecule produced by P. aeruginosa and strains of the B. cepacia complex. It induces the production of IL-8 in 16HBE human bronchial epithelial cells when used at a concentration of 100 μM. Supernatants from 3-oxo-C12-HSL-stimulated 16HBE cells induce chemotaxis of isolated human neutrophils. 3-oxo-C12-HSL has been found in respiratory secretions from patients with cystic fibrosis infected with P. aeruginosa.

Uses

N-(3-Oxododecanoyl)-L-homoserine Lactone is a bacterial quorum sensing signal molecule. Inhibits lymphocyte proliferation and TNF-α and IL-12 production by LPS-stimulated macrophages. Inhibits or promotes antibody production at high and low concentrations, respectively, in keyhole limpet hemocyanin (KLH)-stimulated spleen cells.

Biochem/physiol Actions

N-(3-oxododecanoyl)homoserine-L-lactone (3-oxo-C12-HSL) is among a group of homoserine lactones that includes: N-octanoyl-homoserine lactone (N-C8-HSL), N-(3-oxodecanoyl) homoserine-L-lactone (3-oxo-C10 HSL), N-(3-Oxotetradecanoyl)-L-homoserine lactone (3-oxo-C14-HSL, N-(3-hydroxydecanoyl)-L-homoserine lactone, and N-(3-hydroxyoctanoyl)-L-homoserine lactone involved in the processes of bacterial quorum sensing. These N-acyl-homoserine lactones are used to study the processes and mechanisms of bacterial quorum sensing.

references

[1]. henke jm, bassler bl. bacterial social engagements. trends cell biol. 2004 nov;14(11):648-56.[2]. chambers ce, visser mb, schwab u, et al. identification of n-acylhomoserine lactones in mucopurulent respiratory secretions from cystic fibrosis patients. fems microbiol lett. 2005 mar 15;244(2):297-304.[3]. smith rs, fedyk er, springer ta, et al. il-8 production in human lung fibroblasts and epithelial cells activated by the pseudomonas autoinducer n-3-oxododecanoyl homoserine lactone is transcriptionally regulated by nf-kappa b and activator protein-2. j immunol. 2001 jul 1;167(1):366-74.

Upstream product

• 596104-60-8 (2-nonyl-[1,3]dioxolan-2-yl)-acetic acid 
• 71989-28-1 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine 
• 67342-99-8 ethyl 3-oxododecanoate 
• 182359-65-5 5-decanoyl-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 2185-02-6 L-homoserine lactone 
• 2185-03-7 L-homoserine lactone hydrochloride 
• 6305-38-0 (S)-(-)-α-amino-γ-butyrolactone hydrobromide 
• 429675-23-0 5-(1-hydroxydecylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 182359-61-1 (S)-2-(2-nonyl-1,3-dioxolan-2-yl)-N-(2-oxotetrahydrofuran-3-yl)acetamide 
• 112-12-9 methyl nonyl ketone 
• 334-48-5 1-decanoic acid 
• 112-13-0 n-decanoyl chloride 
• 76835-64-8 methyl 3-oxododecanoate 
• 61058-75-1 3-oxo-dodecanoic acid 

Downstream Products

• 182359-60-0 N-(3-hydroxy-dodecanoyl)-L-homoserine lactone 

Relevant articles and documents

Synthesis of new chalcone-based homoserine lactones and their antiproliferative activity evaluation

Three series of new homoserine lactone analogs were efficiently synthesized starting from methionine and further evaluated for their antiproliferative activity against different cancer cell lines. Among these compounds, some of the chalcone containing compounds 6a-n showed acceptable antiproliferative activity against prostate cancer cells DU145 and PC-3 with the IC50 values less than 10 μM. Compounds 6c, 6e and 6h inhibited growth of DU145 and PC-3 cells at low micromolar levels with the IC50 values ranging from 3.0 to 5.0 μM, much more potent than natural OdDHL. Compound 6e concentration-dependently inhibited colony formation and cell migration of DU145 cells. A synergistic effect on the growth inhibition and the apoptosis of DU145 cells was observed when compound 6e was used in combination with TRAIL. OdDHL or 6e treatment concentration-dependently activated TRAIL death receptor DR5 which may account for the observed synergistic effect of 6e or OdDHL with TRAIL on the growth inhibition and cell apoptosis. Compound 6e also inhibited migration of DU145 cells in a time- and concentration-dependent manner. The data suggest that quorum sensing molecules OdDHL and 6e may improve the sensitivity of DU145 cells toward TRAIL via activating DR5, compound 6e may be used as a potential lead compound for developing new TRAIL receptor agonists.

Molecular insights into the impact of oxidative stress on the quorum-sensing regulator protein LasR

The LasR regulator protein functions at the top of the Pseudomonas aeruginosa quorum-sensing hierarchy and is implicated in promoting bacterial virulence. Of note is recent evidence that this transcription factor may also respond to oxidative stress. Here, all cysteines in LasR were inspected to deduce their redox sensitivity and to probe the connection between stress response and LasR activity using purified LasR and individual LasR domains. Cys79 in the ligand binding domain of LasR appears to be important for ligand recognition and folding of this domain to potentiate DNA binding but does not seem to be sensitive to oxidative stress when bound to its native ligand. Two cysteines in the DNA binding domain of LasR do form a disulfide bond when treated with hydrogen peroxide, and formation of this Cys201-Cys203 disulfide bond appears to disrupt the DNA binding activity of the transcription factor. Mutagenesis of either of these cysteines leads to expression of a protein that no longer binds DNA. A cell-based reporter assay linking LasR function with β-galactosidase activity gave results consistent with those obtained with purified LasR. This work provides a possible mechanism for oxidative stress response by LasR and indicates that multiple cysteines within the protein may prove to be useful targets for disabling its activity.

Targeting Staphylococcus aureus quorum sensing with nonpeptidic small molecule inhibitors

A series of 3-oxo-C12-HSL, tetramic acid, and tetronic acid analogues were synthesized to gain insights into the structural requirements for quorum sensing inhibition in Staphylococcus aureus. Compounds active against agr were noncompetitive inhibitors of the autoinducing peptide (AIP) activated AgrC receptor, by altering the activation efficacy of the cognate AIP-1. They appeared to act as negative allosteric modulators and are exemplified by 3-tetradecanoyltetronic acid 17, which reduced nasal cell colonization and arthritis in a murine infection model.