C8-Ceramide

• CAT Number: R020636
• CAS Number: 74713-59-0
• Molecular Formula: C26H51NO3
• Molecular Weight: 425.69
• Purity: ≥95%
• Synonyms: N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]octanamide
• InChI: InChI=1S/C26H51NO3/c1-3-5-7-9-10-11-12-13-14-15-16-18-19-21-25(29)24(23-28)27-26(30)22-20-17-8-6-4-2/h19,21,24-25,28-29H,3-18,20,22-23H2,1-2H3,(H,27,30)/b21-19+/t24-,25+/m0/s1
• InChIKey: APDLCSPGWPLYEQ-WRBRXSDHSA-N
• SMILES: CCCCCCCCCCCCCC=CC(C(CO)NC(=O)CCCCCCC)O

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].
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].
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].

Reference

[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.
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[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.
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[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.
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[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.
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[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.
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