Home>>Lipids>> Sphingolipids>>C20 Ceramide (d18:1/20:0)

C20 Ceramide (d18:1/20:0)

(Synonyms: N-二十酰-D-神经鞘氨醇,Cer(d18:1/20:0)) 目录号 : GC43067

C20 Ceramide (d18:1/20:0)是一种生物活性鞘脂,也是神经酰胺的一种,含有20个碳的脂肪酸链(20:0)和18个碳的鞘氨醇骨架(d18:1)。

C20 Ceramide (d18:1/20:0) Chemical Structure

Cas No.:7344-02-7

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Sample solution is provided at 25 µL, 10mM.

Description

C20 Ceramide (d18:1/20:0) is a bioactive sphingolipid and a type of ceramide, containing a 20-carbon fatty acid chain (20:0) and an 18-carbon sphingosine backbone(d18:1).C20 Ceramide (d18:1/20:0) plays important roles in cellular signaling, particularly in apoptosis[1], cell cycle regulation, and stress responses[2].C20 Ceramide (d18:1/20:0) is commonly utilized in neurobiology research and cancer therpy[3], particularly in the study of its potential in Alzheimer's disease[4]. C20 Ceramide (d18:1/20:0) acts as a standard in quantification of ceramide species in biological samples by liquid chromatography electrospray ionization tandem mass spectrometry[5].

C20 Ceramide (d18:1/20:0) (2µM; 24h) treatment can induce apoptosis in primary cultured astrocytes from presenilin 1 (PS1) knock-in (PS1M146V) mice but not in wild-type astrocytes[6].

C20 Ceramide (d18:1/20:0) is elevated in presenilin 1 (PS1) knock-in (PS1M146V) mice brain[6].C20 Ceramide (d18:1/20:0) infusions of 100µM every other day for two weeks into the ventral hippocampus (VH) of adult male and female rats with implanted cannulas can trigger anhedonia-like behavior in the rats[7].

References:
[1]. Watts JD, Gu M, Patterson SD, Aebersold R, Polverino AJ. On the complexities of ceramide changes in cells undergoing apoptosis: lack of evidence for a second messenger function in apoptotic induction. Cell Death Differ. 1999 Feb;6(2):105-14. doi: 10.1038/sj.cdd.4400472. PMID: 10200556.
[2]. Kim HE, Grant AR, Simic MS, et al. Lipid Biosynthesis Coordinates a Mitochondrial-to-Cytosolic Stress Response. Cell. 2016 Sep 8;166(6):1539-1552.e16. doi: 10.1016/j.cell.2016.08.027. PMID: 27610574; PMCID: PMC5922983.
[3]. Sheridan M, Ogretmen B. The Role of Ceramide Metabolism and Signaling in the Regulation of Mitophagy and Cancer Therapy. Cancers (Basel). 2021 May 19;13(10):2475. doi: 10.3390/cancers13102475. PMID: 34069611; PMCID: PMC8161379.
[4]. Liu X, Jin Y, Cheng X, et al. The relevance between abnormally elevated serum ceramide and cognitive impairment in Alzheimer's disease model mice and its mechanism. Psychopharmacology (Berl). 2024 Mar;241(3):525-542. doi: 10.1007/s00213-024-06530-y. Epub 2024 Jan 26. PMID: 38277004.
[5]. Kasumov T, Huang H, Chung YM, et al. Quantification of ceramide species in biological samples by liquid chromatography electrospray ionization tandem mass spectrometry. Anal Biochem. 2010 Jun 1;401(1):154-61. doi: 10.1016/j.ab.2010.02.023. Epub 2010 Feb 21. PMID: 20178771; PMCID: PMC2872137.
[6]. Wang G, Silva J, Dasgupta S, Bieberich E. Long-chain ceramide is elevated in presenilin 1 (PS1M146V) mouse brain and induces apoptosis in PS1 astrocytes. Glia. 2008 Mar;56(4):449-56. doi: 10.1002/glia.20626. PMID: 18205190.
[7]. Sambolín-Escobales L, Feliciano-Quiñones A, Tirado-Castro L, et al. Infusion of C20:0 ceramide into ventral hippocampus triggers anhedonia-like behavior in female and male rats. Front Behav Neurosci. 2022 Aug 24;16:899627. doi: 10.3389/fnbeh.2022.899627. PMID: 36090653; PMCID: PMC9449580.

C20 Ceramide (d18:1/20:0)是一种生物活性鞘脂,也是神经酰胺的一种,含有20个碳的脂肪酸链(20:0)和18个碳的鞘氨醇骨架(d18:1)。C20 Ceramide (d18:1/20:0)在细胞信号传导中发挥重要作用,特别是在细胞凋亡[1]、细胞周期调控和应激反应中[2]。C20 Ceramide (d18:1/20:0)常用于神经生物学研究和癌症治疗[3],尤其是研究其在阿尔茨海默病中的潜在作用[4]。C20 Ceramide (d18:1/20:0)可作为标准品,用于液相色谱电喷雾电离串联质谱法定量检测生物样本中神经酰胺[5]

C20 Ceramide (d18:1/20:0)(2µM;24小时)处理可在早老素1(PS1)敲入(PS1M146V)小鼠来源的原代培养星形胶质细胞中诱导凋亡,但在野生型星形胶质细胞中则不能[6]

在早老素1(PS1M146V)小鼠的大脑中,C20 Ceramide (d18:1/20:0)水平升高[6]。通过植入导管,连续两周每两天向成年雄性和雌性大鼠的腹侧海马(VH)中注入100µM的C20 Ceramide (d18:1/20:0)可在大鼠中引发类似快感缺失的行为[7]

实验参考方法

Cell experiment [1]:

Cell lines

Astrocytes from presenilin 1(PS1) mice

Preparation Method

Primary cultured astrocytes from presenilin 1(PS1) mice were incubated for 24h with 2µM C20 Ceramide (d18:1/20:0) , or vehicle (1:1000 ethanol/2% dodecane). Cells were fixed and stained for Hoechst was performed. Quantification of apoptosis induced by ceramide by counting cells with condensed nuclei. More than 200 cells were counted for each experiment.

Reaction Conditions

2µM; 24h

Applications

C20 Ceramide (d18:1/20:0) can induce apoptosis of primary cultured astrocytes from presenilin 1(PS1) mice.
Animal experiment [2]:

Animal models

Sprague Dawley rats

Preparation Method

Adult male and female rats were implanted with cannulas in the ventral hippocampus (VH) and infused with 100µM C20 Ceramide (d18:1/20:0) or vehicle every other day for 2 weeks. Anhedonia-like behavior was assessed with the sucrose preference test 24h after each VH infusion of C20 Ceramide (d18:1/20:0).

Dosage form

100µM; Every other day; 2 weeks; i.p.

Applications

Localized ventral hippocampus infusions of C20 Ceramide (d18:1/20:0) can induce anhedonia-like behavior in male and female rats

References:
[1]. Wang G, Silva J, Dasgupta S, Bieberich E. Long-chain ceramide is elevated in presenilin 1 (PS1M146V) mouse brain and induces apoptosis in PS1 astrocytes. Glia. 2008 Mar;56(4):449-56. doi: 10.1002/glia.20626. PMID: 18205190.
[2]. Sambolín-Escobales L, Feliciano-Quiñones A, Tirado-Castro L, et al. Infusion of C20:0 ceramide into ventral hippocampus triggers anhedonia-like behavior in female and male rats. Front Behav Neurosci. 2022 Aug 24;16:899627. doi: 10.3389/fnbeh.2022.899627. PMID: 36090653; PMCID: PMC9449580.

化学性质

Cas No. 7344-02-7 SDF
别名 N-二十酰-D-神经鞘氨醇,Cer(d18:1/20:0)
化学名 N-[2R-hydroxy-1S-(hydroxymethyl)-3E-heptadecen-1-yl]-eicosanamide
Canonical SMILES CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](NC(CCCCCCCCCCCCCCCCCCC)=O)CO
分子式 C38H75NO3 分子量 594
溶解度 Ethanol: 6mg/ml 储存条件 Store at -20°C
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1 mM 1.6835 mL 8.4175 mL 16.835 mL
5 mM 0.3367 mL 1.6835 mL 3.367 mL
10 mM 0.1684 mL 0.8418 mL 1.6835 mL
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