N-3-oxo-dodecanoyl-L-Homoserine lactone
(Synonyms: 3-oxo-C12-HSL) 目录号 : GC17279
N-3-氧代-十二烷酰基-L-单丝氨酸内酯（3-氧代-C12-HSL）作为胃肠道中革兰氏阴性菌产生的群体感应（QS）分子，是由高水平的细胞内活性氧（ROS）指示的氧化应激的主要诱导剂。
Cas No.:168982-69-2
Sample solution is provided at 25 µL, 10mM.
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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.
N-3-氧代-十二烷酰基-L-单丝氨酸内酯（3-氧代-C12-HSL）作为胃肠道中革兰氏阴性菌产生的群体感应（QS）分子，是由高水平的细胞内活性氧（ROS）指示的氧化应激的主要诱导剂[1]。
在体外，100μM 3-氧代-C12 HSL提高血小板中的细胞内游离钙，3-氧代C12 HSL诱导细胞内钙依赖性ROS的产生[2]。在体外，3-氧代-12-HSL在10μM时也显著抑制LPS（脂多糖）诱导的IL-6释放，而100μM时IL-6释放减少了近75%[3]。在体外，用50μM 3氧代-C12-HSL处理成纤维细胞1或3小时（与10μM和对照相比）导致线粒体网络的快速断裂，线粒体长度和面积减少以及小线粒体数量增加就是明证[4]。此外，50μM 3氧代-C12-HSL可增加巨噬细胞的细胞面积和前突活性[5]。
在体内，在抗原暴露前1小时接受3-氧代-12-HSL（3 mg/kg）治疗的被动致敏小鼠的PCA（被动皮肤过敏反应）反应显著降低（60%）[3]。
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Cell experiment [1]: |
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Cell lines |
Platelet cells |
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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. |
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Reaction Conditions |
100 μM；300 s |
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Applications |
3-oxo-C12 HSL induces intracellular calcium in a dose-dependent manner, and the maximum rise was obtained at 100 μM |
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Animal experiment [2]: |
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Animal models |
8 week-old C57BL/6 mice or in 6 week-old athymic nude mice |
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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. |
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Dosage form |
25 mg/kg/day; i.p. |
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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. |
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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. |
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| Cas No. | 168982-69-2 | SDF | |
| 别名 | 3-oxo-C12-HSL | ||
| 化学名 | 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-dodecanamide | ||
| Canonical SMILES | CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O | ||
| 分子式 | C16H27NO4 | 分子量 | 297.4 |
| 溶解度 | ≤20mg/ml in DMSO;20mg/ml in dimethyl formamide | 储存条件 | Store at -20°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.3625 mL | 16.8124 mL | 33.6247 mL |
| 5 mM | 0.6725 mL | 3.3625 mL | 6.7249 mL |
| 10 mM | 0.3362 mL | 1.6812 mL | 3.3625 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
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| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
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2.
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Quality Control & SDS
- View current batch:
- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet