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C24:1 Ceramide (d18:1/24:1(15Z))

(Synonyms: Ceramide (d18:1/24:1(15Z)); Cer(d18:1/24:1(15Z)); Nervonic Ceramide; N-Nervonoyl-D-erythro-Sphingosine) 目录号 : GC43078

C24:1 Ceramide (d18:1/24:1(15Z))是一种丰富的天然存在的神经酰胺,神经酰胺调节许多不同的生物活动,例如细胞凋亡、细胞分化、平滑肌细胞增殖和线粒体呼吸链的抑制等。

C24:1 Ceramide (d18:1/24:1(15Z)) Chemical Structure

Cas No.:54164-50-0

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Sample solution is provided at 25 µL, 10mM.

Description

C24:1 Ceramide (d18:1/24:1(15Z)) is an abundant naturally occurring ceramide that regulates many different biological activities, such as apoptosis, cell differentiation, smooth muscle cell proliferation, and inhibition of the mitochondrial respiratory chain[1, 2]. C24:1 Ceramide is abundantly expressed in brain tissue and accumulates in patients with Gaucher disease[3]. C24:1 Ceramide can be used as a standard hexosylceramide for hydrophilic interaction chromatography-based liquid chromatography-mass spectrometry[4].

In vitro, C24:1 Ceramide (1μM) treatment of ependymal cells for 48h induced cell ciliary elongation[5].

References:
[1] Manni M M, Sot J, Arretxe E, et al. The fatty acids of sphingomyelins and ceramides in mammalian tissues and cultured cells: Biophysical and physiological implications[J]. Chemistry and physics of lipids, 2018, 217: 29-34.
[2] Birbes H, El Bawab S, Obeid L M, et al. Mitochondria and ceramide: intertwined roles in regulation of apoptosis[J]. Advances in enzyme regulation, 2002, 42: 113-129.
[3] Nagata M, Izumi Y, Ishikawa E, et al. Intracellular metabolite β-glucosylceramide is an endogenous Mincle ligand possessing immunostimulatory activity[J]. Proceedings of the National Academy of Sciences, 2017, 114(16): E3285-E3294.
[4] Von Gerichten J, Schlosser K, Lamprecht D, et al. Diastereomer-specific quantification of bioactive hexosylceramides from bacteria and mammals [S][J]. Journal of lipid research, 2017, 58(6): 1247-1258.
[5] Kong J N, Hardin K, Dinkins M, et al. Regulation of Chlamydomonas flagella and ependymal cell motile cilia by ceramide-mediated translocation of GSK3[J]. Molecular biology of the cell, 2015, 26(24): 4451-4465.

C24:1 Ceramide (d18:1/24:1(15Z))是一种丰富的天然存在的神经酰胺,神经酰胺调节许多不同的生物活动,例如细胞凋亡、细胞分化、平滑肌细胞增殖和线粒体呼吸链的抑制等[1, 2]。C24:1 Ceramide在脑组织中大量表达,并在戈谢病患者中大量积累[3]。C24:1 Ceramide能够作为基于亲水相互作用色谱的液相色谱质谱法的标准己糖神经酰胺[4]

在体外,C24:1 Ceramide(1μM)处理室管膜细胞48h,诱导了细胞纤毛伸长[5]

实验参考方法

Cell experiment [1]:

Cell lines

Ependymal cells

Preparation Method

Quantitation of motile cilium length in ependymal cells treated for 48h with ceramide biosynthesis inhibitors (5μM myriocin, 10μM FB1) with or without exogenous C24:1 ceramide (1μM).

Reaction Conditions

1μM; 48h

Applications

Addition of C24:1 ceramide to the culture medium rescued cilia in cells treated with FB1 and induced elongation of cilia in cells not treated with ceramide biosynthesis inhibitors.

References:
[1]Kong J N, Hardin K, Dinkins M, et al. Regulation of Chlamydomonas flagella and ependymal cell motile cilia by ceramide-mediated translocation of GSK3[J]. Molecular biology of the cell, 2015, 26(24): 4451-4465.

化学性质

Cas No. 54164-50-0 SDF
别名 Ceramide (d18:1/24:1(15Z)); Cer(d18:1/24:1(15Z)); Nervonic Ceramide; N-Nervonoyl-D-erythro-Sphingosine
化学名 N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-15Z-tetracosenamide
Canonical SMILES OC[C@H](NC(CCCCCCCCCCCCC/C=C\CCCCCCCC)=O)[C@H](O)/C=C/CCCCCCCCCCCCC
分子式 C42H81NO3 分子量 648.1
溶解度 3mg/ml in ethanol; <20ug/ml in DMSO; >5.5mg/ml in DMF 储存条件 Store at -20°C
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1 mM 1.543 mL 7.7149 mL 15.4297 mL
5 mM 0.3086 mL 1.543 mL 3.0859 mL
10 mM 0.1543 mL 0.7715 mL 1.543 mL
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