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C22 Ceramide (d18:1/22:0)

(Synonyms: C22 Ceramide;Cer(d18:1/22:0);Ceramide (d18:1/22:0)) 目录号 : GC43069

C22 Ceramide (d18:1/22:0)是一种从海绵Haliclona koremella中分离的含有山萮酸的长链神经酰胺,是一种内源性生物活性鞘脂。

C22 Ceramide (d18:1/22:0) Chemical Structure

Cas No.:27888-44-4

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1mg
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Description

C22 Ceramide (d18:1/22:0) is a long-chain ceramide containing behenic acid isolated from the sea sponge Haliclona koremella and is an endogenous bioactive sphingolipid. C22 Ceramide (d18:1/22:0) is widely used to study lipid-mediated signal transduction mechanisms that affect cell homeostasis, apoptosis, and differentiation[1][2]. C22 Ceramide (d18:1/22:0) can also be used as a standard for measuring ceramide concentration in samples by high-performance liquid chromatography/tandem mass spectrometry (LC/MS2) and as a standard for the quantification of sphingolipid metabolites[3][4].

C22 Ceramide (d18:1/22:0) (40nmol; 15min) reduces the propensity of C16-ceramide channel formation in isolated rat liver mitochondria and in liposomes[1]. C22 ceramide (d18:1/22:0) can inhibit the mitochondrial to cytoplasmic stress response induced by hsp-6 RNAi[2]. C22 Ceramide (d18:1/22:0) (0.2µM; 48h) activated miR-199a-3p and inhibited mammalian target of rapamycin(mTOR) level, thus activating the mTOR-ULK1 signaling pathway by promoting the expression of unc-51-like autophagy activating kinase 1 (ULK1), B-cell lymphoma-2 (Bcl-2), Beclin-1, autophagy-related gene 5 (ATG5), and microtubule-associated protein light chain 3 (LC3-II) and degrading p62[5].

References:
[1]. Stiban J, Perera M. Very long chain ceramides interfere with C16-ceramide-induced channel formation: A plausible mechanism for regulating the initiation of intrinsic apoptosis[J]. Biochimica et Biophysica Acta (BBA)-Biomembranes, 2015, 1848(2): 561-567.
[2]. Kim H E, Grant A R, Simic M S, et al. Lipid biosynthesis coordinates a mitochondrial-to-cytosolic stress response[J]. Cell, 2016, 166(6): 1539-1552. e16.
[3]. Kauhanen D, Sysi-Aho M, Koistinen K M, et al. Development and validation of a high-throughput LC–MS/MS assay for routine measurement of molecular ceramides[J]. Analytical and bioanalytical chemistry, 2016, 408: 3475-3483.
[4]. Aslan M, Afşar E, Kırımlıoglu E, et al. Antiproliferative effects of thymoquinone in MCF-7 breast and HepG2 liver cancer cells: possible role of ceramide and ER stress[J]. Nutrition and Cancer, 2021, 73(3): 460-472.
[5]. Wan J, Zhang S, Li G, et al. Ceramide Ehux-C22 Targets the miR-199a-3p/mTOR Signaling Pathway to Regulate Melanosomal Autophagy in Mouse B16 Cells[J]. International Journal of Molecular Sciences, 2024, 25(15): 8061.

C22 Ceramide (d18:1/22:0)是一种从海绵Haliclona koremella中分离的含有山萮酸的长链神经酰胺,是一种内源性生物活性鞘脂。C22 Ceramide (d18:1/22:0)广泛用于细胞稳态、凋亡和分化的脂质介导信号转导机制的研究[1][2]。C22 Ceramide (d18:1/22:0)还可以用作高效液相色谱/串联质谱(LC/MS2)测量样品中神经酰胺浓度的标准品,以及定量鞘脂代谢物的标准品[3][4]

C22 Ceramide (d18:1/22:0)(40nmol;15min)降低了分离的大鼠肝线粒体和脂质体中C16-神经酰胺通道的形成[1]。C22 Ceramide (d18:1/22:0)能够抑制hsp-6 RNAi诱导的线粒体到细胞质的应激反应[2]。C22 Ceramide (d18:1/22:0)(0.2µM; 48h)激活miR-199a-3p并抑制哺乳动物雷帕霉素靶蛋白(mTOR)水平,从而通过促进unc-51样自噬激活激酶1(ULK1)、B细胞淋巴瘤-2(Bcl-2)、Beclin-1、自噬相关基因5(ATG5)和微管相关蛋白轻链3(LC3-II)的表达并降解p62来激活mTOR-ULK1信号通路[5]

实验参考方法

Cell experiment [1]:

Cell lines

B16 cells

Preparation Method

B16 cells were cultured with RPMI 1640 medium provided with 10% FBS and 1% PS (5% CO2, 37°C) overnight. Dissolved in DMSO and MTBE (1:1), 2µM C22 Ceramide (d18:1/22:0) was added to the cell.

Reaction Conditions

0.2µM; 48h

Applications

C22 Ceramide (d18:1/22:0) activated miR-199a-3p and inhibited mammalian target of rapamycin(mTOR) level, thus activating the mTOR-ULK1 signaling pathway by promoting the expression of unc-51-like autophagy activating kinase 1 (ULK1), B-cell lymphoma-2 (Bcl-2), Beclin-1, autophagy-related gene 5 (ATG5), and microtubule-associated protein light chain 3 (LC3-II) and degrading p62.

References:
[1]. Wan J, Zhang S, Li G, et al. Ceramide Ehux-C22 Targets the miR-199a-3p/mTOR Signaling Pathway to Regulate Melanosomal Autophagy in Mouse B16 Cells[J]. International Journal of Molecular Sciences, 2024, 25(15): 8061.

化学性质

Cas No. 27888-44-4 SDF
别名 C22 Ceramide;Cer(d18:1/22:0);Ceramide (d18:1/22:0)
化学名 N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-docosanamide
Canonical SMILES OC[C@H](NC(CCCCCCCCCCCCCCCCCCCCC)=O)[C@H](O)/C=C/CCCCCCCCCCCCC
分子式 C40H79NO3 分子量 622.1
溶解度 0.15mg/ml in DMF 储存条件 Store at -20°C
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1 mM 1.6075 mL 8.0373 mL 16.0746 mL
5 mM 0.3215 mL 1.6075 mL 3.2149 mL
10 mM 0.1607 mL 0.8037 mL 1.6075 mL
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