C2 Ceramide
(Synonyms: N-乙酰基神经鞘氨醇,C2 Ceramide (d18:1/2:0)， C2 Ceramide ，Ceramide (d18:1/2:0)， Cer(18:1/2:0)，N-acetoyl-D-erythro-sphingosine) 目录号 : GC17011C2 Ceramide是一种短链细胞渗透性神经酰胺类似物，可抑制Bcl2蛋白的磷酸化，IC50值为14μmol/L。
Cas No.:3102-57-6
Sample solution is provided at 25 µL, 10mM.
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C2 Ceramide is a short-chain cell-permeable ceramide analogue that inhibits the protein Bcl2 phosphorylation with an IC50 value of 14μmol/L [1]. C2 Ceramide serves as an effective research tool for tumor cell apoptosis studies because C2 Ceramide can activate apoptosis in nearly all cell types[2].
In vitro, C2 Ceramide exhibited the IC50 value of 39µmol/L toward HEp-2 cells for 24h[3]. C2 Ceramide caused the inhibition of HERG potassium channel current in HEK293 cells with an IC50 value of 19.5μmol/L after 10h treatment[4]. C2 Ceramide (25μmol/L, 1h) inhibited the mRNA levels and promoter activities of MMP-1, MMP-3 and MMP-9 in U87MG glioma cells, and suppressed cell migration[5]. The application of C2 Ceramide at a concentration of 50μmol/L for 60 minutes blocked the production of reactive oxygen species triggered by hydrogen peroxide and prevented the resulting cell death in rat primary astrocytes[6].
In vivo, C2 Ceramide treatment at 2.0mg/kg by intraperitoneal injection with Long Evans rat pups for 25 days alleviated the symptoms of hyperglycemia, hyperlipidemia and mild steatohepatitis, reduced the lipid content in the brain, and increased the ceramide levels in the liver, brain and serum[7]. The administration of 120μmol/L C2 Ceramide by gavage for 12 hours resulted in a significant reduction of mRNA and protein expression levels of HNF-1 and GSTA1 in the liver of adult male Kunming mice with acetaminophen-induced acute liver injury[8].
References:
[1] Ruvolo P P, Deng X, Ito T, et al. Ceramide induces Bcl2 dephosphorylation via a mechanism involving mitochondrial PP2A[J]. Journal of Biological Chemistry, 1999, 274(29): 20296-20300.
[2] Wagenknecht B, Roth W, Gulbins E, et al. C2-ceramide signaling in glioma cells: synergistic enhancement of CD95-mediated, caspase-dependent apoptosis[J]. Cell Death & Differentiation, 2001, 8(6): 595-602.
[3] Oğuz O, Manole F, Bayar Muluk N, et al. Effects of ceramide C2 application on human laryngeal carcinoma cells: a cell culture study[J]. Eur Rev Med Pharmacol Sci, 2023, 27(5 Suppl): 109-120.
[4] Bai Y, Wang J, Shan H, et al. Sphingolipid metabolite ceramide causes metabolic perturbation contributing to HERG K+ channel dysfunction[J]. Cellular Physiology and Biochemistry, 2007, 20(5): 429-440.
[5] Jung J S, Ahn Y H, Moon B I, et al. Exogenous C2 ceramide suppresses matrix metalloproteinase gene expression by inhibiting ROS production and MAPK signaling pathways in PMA-stimulated human astroglioma cells[J]. International Journal of Molecular Sciences, 2016, 17(4): 477.
[6] Jung J S, Choi M J, Ko H M, et al. Short-chain C2 ceramide induces heme oxygenase-1 expression by upregulating AMPK and MAPK signaling pathways in rat primary astrocytes[J]. Neurochemistry international, 2016, 94: 39-47.
[7] de la Monte S M, Tong M, Nguyen V A, et al. Ceramide-mediated insulin resistance and impairment of cognitive-motor functions[J]. Journal of Alzheimer’s Disease, 2010, 21(3): 967-984.
[8] Ma X, Chang Y, Zhang Y, et al. Effects of C2-ceramide and oltipraz on hepatocyte nuclear factor-1 and glutathione S-transferase A1 in acetaminophen-mediated acute mice liver injury[J]. Frontiers in Pharmacology, 2018, 9: 1009.
C2 Ceramide是一种短链细胞渗透性神经酰胺类似物，可抑制Bcl2蛋白的磷酸化，IC50值为14μmol/L[1]。C2 Ceramide可以激活几乎所有细胞类型的凋亡，是肿瘤细胞凋亡研究的有效工具[2]。
在体外，C2 Ceramide对HEp-2细胞处理24小时的IC50值为39µmol/L[3]。C2 Ceramide处理10小时后，可抑制HEK293细胞中的HERG钾通道电流，IC50值为19.5μmol/L[4]。C2 Ceramide（25μmol/L, 1h）抑制U87MG胶质瘤细胞MMP-1、MMP-3和MMP-9 mRNA水平和启动子活性，抑制细胞迁移[5]。C2 Ceramide在50μmol/L浓度下作用60分钟，可阻断大鼠原代星形胶质细胞中由过氧化氢引起的活性氧的产生，防止大鼠原代星形胶质细胞死亡[6]。
在体内，C2 Ceramide以2.0mg/kg剂量腹腔注射处理Long Evans大鼠幼崽25天，可缓解高血糖、高脂血症和轻度脂肪性肝炎症状，降低脑内脂质含量，提高肝、脑和血清中神经酰胺水平[7]。通过灌胃给予120μmol/L C2神经酰胺12小时后，对乙酰氨基酚诱导的急性肝损伤成年昆明雄性小鼠肝脏中HNF-1和GSTA1的mRNA及蛋白表达水平均显著降低[8]。
| Cell experiment [1]: | |
Cell lines | HN4 and HN30 cell lines |
Preparation Method | The HN4 and HN30 cell lines were seeded at a density of 1×104 cells per well into 96-well plates with each well containing 100μL of medium. Cells received treatment with C2 Ceramide at concentrations of 0, 20, 40, and 60μmol/L and combinations of C2 Ceramide with autophagy inhibitor CQ at 5μmol/L, necroptosis inhibitor Nec-1 at 5μmol/L, or MEK inhibitor PD98059 at 10μmol/L for 24 hours starting from 24 hours after cell seeding. A minimum of five wells served as replicates for each experimental group. Following the incubation period, 10μL of CCK-8 reagent from a Cell Counting Kit-8 was added to each well, and cells continued to grow in culture. The microplate reader recorded absorbance at 450nm after adding the CCK-8 reagent for 3 hours. All cells were divided into two groups: a DMSO-treated group and a C2 Ceramide-treated group. The cells underwent treatment for 24 hours before collection. Extract fragmented DNA using DNAiso Reagent following the manufacturer's instructions before performing electrophoresis on 2g/L agarose gels containing 0.5g/L ethidium bromide and visualizing the results with UV transillumination. All experiments were repeated three times. |
Reaction Conditions | 0, 20, 40, and 60μmol/L; 24h |
Applications | C2 Ceramide exhibited concentration-dependent cytotoxicity in HN4 and HN30 cell lines. C2 Ceramide induced both caspase-3-independent apoptosis and necroptosis. |
| Animal experiment [2]: | |
Animal models | C57BL/6 mice |
Preparation Method | The 25 C57BL/6 mice were assigned randomly to five groups which included a control group, a model group, and C2 Ceramide low-, medium-, and high-dose groups each containing five mice. The control group remained untreated, and the mouse model of Parkinson’s disease was generated through the injection of mutant A53T α-Syn oligomers into the left striatum of all other groups. The three C2 Ceramide groups received a single intragastric dose of C2 Ceramide at concentrations of 1, 5, and 10μg/g dissolved in saline on the 30th day after injection into the striatum while control and model groups received the same saline volume between days 30 to 90 for 60 days total. Monitor behavioral changes in the mice across all groups. The mouse brain tissue samples were collected by perfusion while the mice remained under anesthesia on the 90th day post striatal injection before examining dopaminergic neuron changes in the midbrain substantia nigra through immunohistochemical staining. ELISA tests showed α-Syn oligomerization and phosphorylation levels in the mouse midbrain while enzyme activities linked to α-Syn phosphorylation underwent analysis. |
Dosage form | 1, 5, and 10μg/g for 60 days; i.g. |
Applications | C2 Ceramide (10μg/g) treatment significantly reduced the content of α-Syn oligomers and phosphorylated α-Syn, increased the content of ceramide, and up-regulated the activity of protein phosphatase 2A in the brain tissue of mice. |
References: | |
| Cas No. | 3102-57-6 | SDF | |
| 别名 | N-乙酰基神经鞘氨醇,C2 Ceramide (d18:1/2:0)， C2 Ceramide ，Ceramide (d18:1/2:0)， Cer(18:1/2:0)，N-acetoyl-D-erythro-sphingosine | ||
| 化学名 | N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]acetamide | ||
| Canonical SMILES | CCCCCCCCCCCCCC=CC(C(CO)NC(=O)C)O | ||
| 分子式 | C20H39NO3 | 分子量 | 341.53 |
| 溶解度 | DMF: >22 mg/ml (from C-8 Ceramide),DMSO: >20 mg/ml (from C-8 Ceramide),Ethanol: >33 mg/ml (from C-8 Ceramide),PBS pH 7.2: <50 µ g/ml (from C-8 Ceramide) | 储存条件 | Desiccate at -20°C |
| 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 | 2.928 mL | 14.64 mL | 29.28 mL |
| 5 mM | 0.5856 mL | 2.928 mL | 5.856 mL |
| 10 mM | 0.2928 mL | 1.464 mL | 2.928 mL |
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| 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 | ||||||||||
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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，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
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Quality Control & SDS
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- Purity: >98.00%
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