857450P
Avanti
C6-Pyridinium-Ceramide
D-erythro-2-N-[6′-(1"-pyridinium)-hexanoyl]-sphingosine bromide, powder
Synonym(s):
D-erythro-C6-pyridinium-ceramide; LCL29
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About This Item
Empirical Formula (Hill Notation):
C29H51N2O3Br
CAS Number:
Molecular Weight:
555.63
UNSPSC Code:
12352211
NACRES:
NA.25
assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 1 mg (857450P-1mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 857450P
lipid type
bioactive lipids
sphingolipids
shipped in
dry ice
storage temp.
−20°C
General description
Application
C6-Pyridinium-Ceramide has been used in treating HeLa cell lines, to elucidate its role in alternative splicing and as a standard for high performance liquid chromatography (HPLC).[3] It has also been used in combination with photodynamic therapy for head and neck squamous cancer cell carcinoma[4] and mouse squamous cell carcinoma.[5]
Biochem/physiol Actions
C6-Pyridinium-Ceramide plays an important role in alternative splicing of the gene by inhibiting protein phosphatase-1.[3] C6-Pyridinium-Ceramide (LCL29) acts as an anti-cancer agent. It sensitizes cancer cells when combined with photodynamic therapy.[4] In cancer cells, LCL29 accumulates in the negatively charged mitochondria.[1]
Packaging
5 mL Amber Glass Screw Cap Vial (857450P-1mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
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Sergei A Novgorodov et al.
The Journal of biological chemistry, 280(16), 16096-16105 (2005-02-22)
Ceramide-induced cell death is thought to be mediated by change in mitochondrial function, although the precise mechanism is unclear. Proposed models suggest that ceramide induces cell death through interaction with latent binding sites on the outer or inner mitochondrial membranes
C6-pyridinium ceramide sensitizes SCC17B human head and neck squamous cell carcinoma cells to photodynamic therapy
Boppana NB, et al.
Journal of Photochemistry and Photobiology. B, Biology, 143, 163-168 (2015)
Enhanced tumor cures after Foscan photodynamic therapy combined with the ceramide analog LCL29. Evidence from mouse squamous cell carcinomas for sphingolipids as biomarkers of treatment response
Separovic D, et al.
International journal of oncology, 38(2), 521-527 (2011)
Zdzislaw M Szulc et al.
Bioorganic & medicinal chemistry, 14(21), 7083-7104 (2006-08-22)
In the course of our studies on compartment-specific lipid-mediated cell regulation, we identified an intimate connection between ceramides (Cers) and the mitochondria-dependent death-signaling pathways. Here, we report on a new class of cationic Cer mimics, dubbed ceramidoids, designed to act
C6 pyridinium ceramide influences alternative pre-mRNA splicing by inhibiting protein phosphatase-1
Sumanasekera C, et al.
Nucleic Acids Research, 40(9), 4025-4039 (2011)
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