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

カタログ番号GC43069

C-22セラミドは内因性の生体活性スフィンゴ脂質です。

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C22 Ceramide (d18:1/22:0) 化学構造

Cas No.: 27888-44-4

サイズ 価格 在庫数 個数
1mg
$28.00
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5mg
$84.00
在庫あり
10mg
$140.00
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Sample solution is provided at 25 µL, 10mM.

Product has been cited by 1 publications

Description of C22 Ceramide (d18:1/22:0)

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.

Protocol of C22 Ceramide (d18:1/22:0)

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.

Chemical Properties of C22 Ceramide (d18:1/22:0)

Cas No. 27888-44-4 SDF
同義語 C22 Ceramide;Cer(d18:1/22:0);Ceramide (d18:1/22:0)
Chemical Name 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
Formula C40H79NO3 M.Wt 622.1
溶解度 0.15mg/ml in DMF Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of C22 Ceramide (d18:1/22:0)

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1 mg 5 mg 10 mg
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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Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )

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Review for C22 Ceramide (d18:1/22:0)

Average Rating: 5 ★★★★★ (Based on Reviews and 15 reference(s) in Google Scholar.)

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