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C6 Ceramide (d18:1/6:0)

(Synonyms: N-己酰基-D-神经鞘氨醇,N-hexanoyl-D-erythro-sphingosine) 目录号 : GC11079

C6 Ceramide (d18:1/6:0)是一种短链的、细胞可透过的神经酰胺类似物,在临床前研究中用于模拟内源性神经酰胺的作用。

C6 Ceramide (d18:1/6:0) Chemical Structure

Cas No.:124753-97-5

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1mg
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25mg
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Sample solution is provided at 25 µL, 10mM.

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Description

C6 Ceramide (d18:1/6:0) is a short-chain, cell-permeable analog of ceramide that has been utilized in preclinical studies to mimic the effects of endogenous ceramide[1]. C6 Ceramide (d18:1/6:0) can induce cell death by both apoptosis and necrosis[2]. C6 Ceramide (d18:1/6:0) is primarily used in research areas such as cancer biology[3][4].

C6 Ceramide (d18:1/6:0) (25µM; 24h) treatment strongly reduced cell viability of CTCL cell lines and induced cell death via apoptosis and necrosis[5]. In MDA-231 and MCF-7 cells, treatment with C6 Ceramide (d18:1/6:0) at 10μg/mL for 72 hours dramatically enhances docetaxel-induced cytotoxicity[6].

C6 Ceramide (d18:1/6:0) (60mg/kg; 15d; i.p.) treatment effectively suppresses the growth of CHMp xenograft tumors in mice[7]. C6 Ceramide (d18:1/6:0) (10mg/kg; 6d; i.p.) combined with Trichostatin-A treatment showed significant tumor growth inhibition, increased survival rate and reduced tumor size in mice xenograft pancreatic and ovarian cancer models[8].

References:
[1]. Morad SA, Ryan TE, Neufer PD, et al. Ceramide-tamoxifen regimen targets bioenergetic elements in acute myelogenous leukemia. J Lipid Res. 2016 Jul;57(7):1231-42. doi: 10.1194/jlr.M067389. Epub 2016 May 2. PMID: 27140664; PMCID: PMC4918852.
[2]. Gentil B, Grimot F, Riva C. Commitment to apoptosis by ceramides depends on mitochondrial respiratory function, cytochrome c release and caspase-3 activation in Hep-G2 cells. Mol Cell Biochem. 2003 Dec;254(1-2):203-10. doi: 10.1023/a:1027359832177. PMID: 14674699.
[3]. Flowers M, Fabriás G, Delgado A, et al. C6-ceramide and targeted inhibition of acid ceramidase induce synergistic decreases in breast cancer cell growth. Breast Cancer Res Treat. 2012 Jun;133(2):447-58. doi: 10.1007/s10549-011-1768-8. Epub 2011 Sep 21. PMID: 21935601.
[4]. Fillet M, Bentires-Alj M, Deregowski V, et al. Mechanisms involved in exogenous C2- and C6-ceramide-induced cancer cell toxicity. Biochem Pharmacol. 2003 May 15;65(10):1633-42. doi: 10.1016/s0006-2952(03)00125-4. PMID: 12754099.
[5]. Wilhelm R, Eckes T, Imre G, et al. C6 Ceramide (d18:1/6:0) as a Novel Treatment of Cutaneous T Cell Lymphoma. Cancers (Basel). 2021 Jan 13;13(2):270. doi: 10.3390/cancers13020270. PMID: 33450826; PMCID: PMC7828274.
[6]. Yang L, Zheng LY, Tian Y, et al. C6 ceramide dramatically enhances docetaxel-induced growth inhibition and apoptosis in cultured breast cancer cells: a mechanism study. Exp Cell Res. 2015 Mar 1;332(1):47-59. doi: 10.1016/j.yexcr.2014.12.017. Epub 2015 Jan 6. PMID: 25576381.
[7]. Liu J, Zhao F, Zhang Y, et al. C6 Ceramide Inhibits Canine Mammary Cancer Growth and Metastasis by Targeting EGR3 through JAK1/STAT3 Signaling. Animals (Basel). 2024 Jan 27;14(3):422. doi: 10.3390/ani14030422. PMID: 38338065; PMCID: PMC10854580.
[8]. Zhu QY, Wang Z, Ji C, et al. C6-ceramide synergistically potentiates the anti-tumor effects of histone deacetylase inhibitors via AKT dephosphorylation and α-tubulin hyperacetylation both in vitro and in vivo. Cell Death Dis. 2011 Jan 27;2(1):e117. doi: 10.1038/cddis.2010.96. PMID: 21368888; PMCID: PMC3077291.

C6 Ceramide (d18:1/6:0)是一种短链的、细胞可透过的神经酰胺类似物,在临床前研究中用于模拟内源性神经酰胺的作用[1]。C6 Ceramide (d18:1/6:0)可以通过凋亡和坏死诱导细胞死亡[2]。C6 Ceramide (d18:1/6:0) 主要用于癌症生物学等研究领域[3][4]

C6 Ceramide (d18:1/6:0) (25µM; 24h)处理显著降低了CTCL细胞系的细胞活力,并通过凋亡和坏死诱导细胞死亡[5]。在MDA-231和MCF-7细胞中,使用10μg/mL的C6 Ceramide (d18:1/6:0)处理72小时显著增强了多西他赛引起的细胞毒性[6]

C6 Ceramide (d18:1/6:0) (60mg/kg; 15天; 腹腔注射) 处理有效抑制了小鼠体内CHMp异种移植肿瘤的生长[7]。C6 Ceramide (d18:1/6:0) (10mg/kg; 6天; 腹腔注射) 联合曲古抑菌素A的治疗在小鼠异种移植的胰腺癌和卵巢癌模型中有显著的肿瘤生长抑制效果,增加了生存率并减小了肿瘤体积[8]

实验参考方法

Cell experiment [1]:

Cell lines

HaCaT cells

Preparation Method

HaCaT cells were treated with 1, 5, 10, 25, 50, and 100µM C6 Ceramide (d18:1/6:0) for 24h. Then Cell viability was determined by MTS assay. To measure cell viability, 3×104 HaCaT cells were seeded in 96-well plates in 100µL volume and 10µL MTS was added and incubated at 37C for 1h. The absorbance at 490nm was recorded using the microplate reader.

Reaction Conditions

1, 5, 10, 25, 50, 100µM; 24h

Applications

C6 Ceramide (d18:1/6:0) treatment can significantly reduce the cell viability of HaCaT cells.
Animal experiment [2]:

Animal models

Primary tumor model Mouse

Preparation Method

Primary tumor-bearing mouse were treatment with 60 mg/kg C6 Ceramide (d18:1/6:0) for 15 days, the tumor volume were measure at the end of the experiment.

Dosage form

60mg/kg/d; 15d; i.p.

Applications

C6 Ceramide (d18:1/6:0) treatment effectively suppresses the growth of CHMp xenograft tumors in vivo.

References:
[1]. Wilhelm R, Eckes T, Imre G, et al. C6 Ceramide (d18:1/6:0) as a Novel Treatment of Cutaneous T Cell Lymphoma. Cancers (Basel). 2021 Jan 13;13(2):270. doi: 10.3390/cancers13020270. PMID: 33450826; PMCID: PMC7828274.
[2]. Liu J, Zhao F, Zhang Y, et al. C6 Ceramide Inhibits Canine Mammary Cancer Growth and Metastasis by Targeting EGR3 through JAK1/STAT3 Signaling. Animals (Basel). 2024 Jan 27;14(3):422. doi: 10.3390/ani14030422. PMID: 38338065; PMCID: PMC10854580.

化学性质

Cas No. 124753-97-5 SDF
别名 N-己酰基-D-神经鞘氨醇,N-hexanoyl-D-erythro-sphingosine
化学名 N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-hexanamide
Canonical SMILES CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](NC(CCCCC)=O)CO
分子式 C24H47NO3 分子量 397.6
溶解度 20mg/mL in DMSO, 22mg/mL in DMF, 33mg/mL in Ethanol 储存条件 Store at -20°C
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1 mM 2.5151 mL 12.5755 mL 25.1509 mL
5 mM 0.503 mL 2.5151 mL 5.0302 mL
10 mM 0.2515 mL 1.2575 mL 2.5151 mL
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