GLPBio

N-3-oxo-dodecanoyl-L-Homoserine lactone

Catalog No.: GC17279Purity:>97.00%Synonyms: 3-oxo-C12-HSL
COASDSData Sheet

N-3-oxo-dodecanoyl-L-Homoserine lactone (3-oxo-C12-HSL), as a quorum-sensing (QS) molecule produced by Gram-negative bacteria in the gastrointestinal tract, is a major inducer of oxidative stress indicated by a high level of intracellular reactive oxygen species (ROS).

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N-3-oxo-dodecanoyl-L-Homoserine lactone
Cas No.: 168982-69-2
5mgIn Stock
$25.00
1
10mgIn Stock
$45.00
1
50mgIn Stock
$198.00
1
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Description

N-3-oxo-dodecanoyl-L-Homoserine lactone (3-oxo-C12-HSL), as a quorum-sensing (QS) molecule produced by Gram-negative bacteria in the gastrointestinal tract, is a major inducer of oxidative stress indicated by a high level of intracellular reactive oxygen species (ROS)[1].

In vitro, 100μM 3-oxo-C12 HSL elevates intracellular free calcium in platelet, and 3-oxo-C12 HSL induces intracellular calcium-dependent ROS generation[2]. In vitro, 3-oxo-12-HSL also significantly inhibited LPS (lipopolysaccharides) induced IL-6 release at 10 μM, while 100 μM reduced IL-6 release by almost 75%[3]. In vitro, treatment of fibroblasts with 50 μM 3O-C12-HSL for 1 or 3 h (in contrast to 10 μM and the control) resulted in a rapid fragmentation of mitochondrial network, as evidenced by decreased mitochondrial length and area and an elevated number of small mitochondria[4]. In addition, 50 μM 3O-C12-HSL increases the cell area and protrusive activity of macrophages[5].

In vivo, Passively sensitized mice that had been treated with 3-oxo-12-HSL (3 mg/kg) 1 h prior to antigen exposure showed a significant (60%) decrease in PCA (passive cutaneous anaphylaxis) response[3].

References:
[1] Tao S, et al. Caspase-1-dependent mechanism mediating the harmful impacts of the quorum-sensing molecule N-(3-oxo-dodecanoyl)-l-homoserine lactone on the intestinal cells. J Cell Physiol. 2019 Apr;234(4):3621-3633.
[2] Yadav VK, et al. Pseudomonas aeruginosa quorum sensing molecule N-3-oxo-dodecanoyl-l-homoserine lactone activates human platelets through intracellular calcium-mediated ROS generation. Int J Med Microbiol. 2018 Oct;308(7):858-864.
[3] Khambati I, et al. The bacterial quorum-sensing molecule, N-3-oxo-dodecanoyl-L-homoserine lactone, inhibits mediator release and chemotaxis of murine mast cells. Inflamm Res. 2017 Mar;66(3):259-268.
[4] Josephson H, et al. Pseudomonas aeruginosa N-3-Oxo-Dodecanoyl-Homoserine Lactone Impacts Mitochondrial Networks Morphology, Energetics, and Proteome in Host Cells. Front Microbiol. 2020 May 25;11:1069.
[5]Holm A, et al. Pseudomonas aeruginosa N-3-oxo-dodecanoyl-homoserine Lactone Elicits Changes in Cell Volume, Morphology, and AQP9 Characteristics in Macrophages. Front Cell Infect Microbiol. 2016 Mar 24;6:32. 

Protocol

Cell experiment [1]:

Cell lines

Platelet cells

Preparation method

Platelet cells were incubated with 5 μM Fluo-4 AM for 45–50 min at 37 °C in the dark. After 60 s of baseline, 3-oxo-C12 HSL (100 μM), or DMSO as vehicle control were added in a different set of samples, and after 300 s 1 mM of CaCl2 was added, and fluorescence intensity was recorded up to 600 s.

Reaction Conditions

100 μM；300 s

Applications

3-oxo-C12 HSL induces intracellular calcium in a dose-dependent manner, and the maximum rise was obtained at 100 μM

Animal experiment [2]:

Animal models

8 week-old C57BL/6 mice or in 6 week-old athymic nude mice

Preparation method

For C12 (N-3-oxo-dodecanoyl-L-Homoserine lactone) toxicity studies, DMSO or C12 (25 mg/kg/day) was administered intraperitoneally each day in 8 week-old C57BL/6 mice or in 6 week-old athymic nude mice. For wild-type A549 tumors, animals were treated with C12 for 6 times/week. For Bcl-2 over-expressing A549 cells tumors, DMSO or C12 was administered with C12 each day. For A549-control-shRNA and A549-PON2-shRNA tumors, DMSO or C12 was administered twice every three days. At the end of the experiments, tumors were excised for apoptosis evaluation.

Dosage form

25 mg/kg/day; i.p.

Applications

C12 inhibits lung tumor growth and induces tumor cell apoptosis in vivo. C12 inhibits LLC tumor growth and induces tumor cell apoptosis in vivo in a dose-dependent fashion. C12 induces tumor apoptotic cell death independent of anti-apoptotic Bcl-2 proteins. PON3 (lactonase paraoxonase) expression recovers C12 cytotoxicity in PON2-deficient tumor cells.

References:

[1] Yadav VK, et al. Mechanism underlying N-(3-oxo-dodecanoyl)-L-homoserine lactone mediated intracellular calcium mobilization in human platelets. Blood Cells Mol Dis. 2019 Nov;79:102340.

[2] Zhao G, et al. N-(3-oxo-acyl) homoserine lactone inhibits tumor growth independent of Bcl-2 proteins. Oncotarget. 2016 Feb 2;7(5):5924-42.

Product Documents

Purity:>97.00%Appearance:A solid
COASDSData Sheet

Chemical Properties

CAS No.
168982-69-2
Synonyms
3-oxo-C12-HSL
Chemical Name
3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-dodecanamide
SMILES
CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O
Molecular Formula
C16H27NO4
Molecular Weight
297.4
Solubility
≤20mg/ml in DMSO;20mg/ml in dimethyl formamide
Storage
Store at -20°C, protect from light
General tips
Select a suitable solvent according to the product solubility data. Once prepared, aliquot the stock solution to avoid repeated freeze-thaw cycles.
Use stock solutions within 6 months when stored at -80°C or within 1 month when stored at -20°C.
To improve solubility, warm the tube to 37°C and sonicate it for an appropriate period.
Shipping Condition
Evaluation samples are shipped with blue ice. Other available sizes are shipped at room temperature or with blue ice upon request.

CalculatorsMolarity / Dilution / Molecular Weight / Unit Conversion / In Vivo Formulation / Solubility

g/mol

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