C8-Ceramide

Names

[ Name ]:
C8-Ceramide

[Synonym ]:
08:0 CERAMIDE
C8-D-ERYTHRO-CERAMIDE
N-[(2S,3R,4E)-1,3-Dihydroxy-4-octadecen-2-yl]octanamide
CERAMIDE C8
N-Octanoyl-C18-sphingosine
MFCD00236496
Octanamide, N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-
C8 CERAMINE,D-ERYTHRO
N-OCTANOYL-D-SPHINGOSINE
N-Octanoyl-D-erythro-sp
N-OCTANOYLSPHINGOSINE
N-Octanoyl-D-erythr
N-octanoyl-D-erythro-sphingosine

Biological Activity

[Description]:

C8-Ceramide (N-Octanoyl-D-erythro-sphingosine) is a cell-permeable analog of naturally occurring ceramides. C8-Ceramide has anti-proliferation properties and acts as a potent chemotherapeutic agent. C8-Ceramide stimulates dendritic cells to promote T cell responses upon virus infections. C8-Ceramide induces slight activation of protein kinase (PKC) in vitro[1][2][3][4].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Signaling Pathways >> Epigenetics >> PKC

Research Areas >> Cancer

Signaling Pathways >> Autophagy >> Autophagy

Research Areas >> Inflammation/Immunology

Signaling Pathways >> TGF-beta/Smad >> PKC

[Target]

PKC

apoptosis

autophagy

[In Vitro]

C8-ceramide (3 μM; 48 hours) irreversibly reduces tumor-cell proliferation and induces morphological changes[1]. C8-ceramide can induce necrosis-like cell death, but does not induce caspase-dependent cleavage of PARP (biochemical marker of apoptosis) in human cervical tumor cells[1]. C8-ceramide may increase the endogenous ROS level (10-30 µM; 24 hours) by regulating the switch of SOD1 and SOD2, causing the anti-proliferation (10-50 µM; 24 hours), and consequently triggering the apoptosis (10-50 µM; 48 hours) of NSCLC H1299 cells[2]. Cell Viability Assay[1] Cell Line: CALO cells, INBL cells, HeLa cells Concentration: 3 μM Incubation Time: 48 hours Result: Markedly reduced the tumor cell number. Cell Proliferation Assay[2] Cell Line: H1299 cells Concentration: 10 µM, 20 µM, 30 µM, 40 µM, 50 µM Incubation Time: 24 hours Result: Decreased the rate of cellular proliferation in a dose-dependent manner, with an IC50 of 22.9 µM. Cell Cycle Analysis[2] Cell Line: H1299 cells Concentration: 10 µM, 20 µM, 30 µM, 40 µM, 50 µM Incubation Time: 24 hours Result: Caused the G1 arrest. Apoptosis Analysis[2] Cell Line: H1299 cells Concentration: 10 µM, 20 µM, 30 µM Incubation Time: 24 hours, 48 hours Result: Increased the level of cleaved caspase-3.

[In Vivo]

C8-ceramide (0.1 mg/kg; intranasal administration) induces more robust CD8+ and CD4+ T cell responses to viral infections in virus infected mice[3]. Animal Model: C57BL/6 mice, with lymphocytic choriomeningitis virus infected[2] Dosage: 0.1 mg/kg Administration: Intranasal administration Result: Increased the CD8+ T cell response to influenza in the lungs.

[References]

[1]. Rebeca López-Marure , et al. Ceramide promotes the death of human cervical tumor cells in the absence of biochemical and morphological markers of apoptosis. Biochem Biophys Res Commun. 2002 May 10;293(3):1028-36.

[2]. Yuli C. Chang, et al. Exogenous C8-Ceramide Induces Apoptosis by Overproduction of ROS and the Switch of Superoxide Dismutases SOD1 to SOD2 in Human Lung Cancer Cells. Int J Mol Sci. 2018 Oct; 19(10): 3010.

[3]. Curtis J. Pritzl, et al. A ceramide analogue stimulates dendritic cells to promote T cell responses upon virus infections. J Immunol. 2015 May 1; 194(9): 4339–4349.

[4]. H W Huang, et al. Ceramides modulate protein kinase C activity and perturb the structure of Phosphatidylcholine/Phosphatidylserine bilayers. Biophys J. 1999 Sep; 77(3): 1489–1497.

[5]. Lan Weiss, et al. Ceramide contributes to pathogenesis and may be targeted for therapy in VCP inclusion body myopathy. Hum Mol Genet. 2021 Jan 7;ddaa248.

Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
595.5±50.0 °C at 760 mmHg

[ Melting Point ]:
68-70°C

[ Molecular Formula ]:
C₂₆H₅₁NO₃

[ Molecular Weight ]:
425.688

[ Flash Point ]:
313.9±30.1 °C

[ Exact Mass ]:
425.386902

[ PSA ]:
69.56000

[ LogP ]:
9.09

[ Appearance of Characters ]:
waxy solid

[ Vapour Pressure ]:
0.0±3.8 mmHg at 25°C

[ Index of Refraction ]:
1.482

[ Storage condition ]:
−20°C

[ Stability ]:
Temperature Sensitive

[ Water Solubility ]:
DMSO or ethanol: soluble

MSDS

Click to get detail MSDS

Safety Information

[ Safety Phrases ]:
S24/25

[ WGK Germany ]:
3

[ HS Code ]:
2924199090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2924199090

[ Summary ]:
2924199090. other acyclic amides (including acyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%