N-3-oxo-dodecanoyl-L-homoserine lactone  (Synonyms: OdDHL; N-(3-オキソドデカノイル)-L-ホモセリンラクトン)

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^[1][2].Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density.N-3-oxo-dodecanoyl-L-Homoserine lactone induces the production of IL-8 in 16HBE human bronchial epithelial cells^[3].

N-3-oxo-dodecanoyl-L-homoserine lactone (25-100 μM, 18 h) inhibits the expression of IL-8 in cell L828, and induces chemotaxic of neutrophils through activation of NF-κB and ERK1/2^[3].
N-3-oxo-dodecanoyl-L-homoserine lactone (50 μM, 24 h) induces ER stress response, ROS generation and decreased mitochondrial membrane potential, which causes the activation of caspase 3/8/9/12, thereby leading to apoptosis in BMDMs^[6].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

N-3-oxo-dodecanoyl-L-homoserine lactone (0.3-1 mg/kg, ip, single dose) enhances immune bias of the host animal, exhibits immunomodulatory activity in OVA-immunized mouse models, ameliorates type 1 diabetes by inhibiting the activation and differentiation of naive T cells^[4][5].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

297.39

C₁₆H₂₇NO₄

168982-69-2

Solid

White to light yellow

CCCCCCCCCC(CC(N[C@@H]1C(OCC1)=O)=O)=O

Room temperature in continental US; may vary elsewhere.

4°C, protect from light

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

• [1]. Pearson JP, Gray KM, Passador L, Tucker KD, Eberhard A, Iglewski BH, Greenberg EP. Structure of the autoinducer required for expression of Pseudomonas aeruginosa virulence genes. Proc Natl Acad Sci U S A. 1994 Jan 4;91(1):197-201.  [Content Brief]

  [2]. Chambers CE, Visser MB, Schwab U, Sokol PA. Identification of N-acylhomoserine lactones in mucopurulent respiratory secretions from cystic fibrosis patients. FEMS Microbiol Lett. 2005 Mar 15;244(2):297-304.  [Content Brief]

  [3]. Smith RS, Fedyk ER, Springer TA, Mukaida N, Iglewski BH, Phipps RP. 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 a  [Content Brief]

  [4]. Ritchie AJ, et al., Modification of in vivo and in vitro T- and B-cell-mediated immune responses by the Pseudomonas aeruginosa quorum-sensing molecule N-(3-oxododecanoyl)-L-homoserine lactone. Infect Immun. 2003 Aug;71(8):4421-31.  [Content Brief]

  [5]. Gaisford W, et al., OdDHL inhibits T cell subset differentiation and delays diabetes onset in NOD mice. Clin Vaccine Immunol. 2011 Aug;18(8):1213-20.  [Content Brief]

  [6]. Woo K, et al., N-3-Hydroxy Dodecanoyl-DL-homoserine Lactone (OH-dDHL) Triggers Apoptosis of Bone Marrow-Derived Macrophages through the ER- and Mitochondria-Mediated Pathways. Int J Mol Sci. 2021 Jul 15;22(14):7565.  [Content Brief]