567735

Sphingosylphosphoryl-choline

SPC is the deacylated derivative of sphingomyelin known to accumulate in neuropathic Niemann-Pick disease type A.

• Synonym(s): Sphingosylphosphoryl-choline, SPC, lyso-Sphingomyelin
• Empirical Formula (Hill Notation): C₂₃H₄₉N₂O₅P
• CAS Number: 1670-26-4
• Molecular Weight: 464.62
• MDL number: MFCD02259287
• UNSPSC Code: 12352211
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥98% (TLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; desiccated
• color: white
• solubility: chloroform/methanol (2:1): 1 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: [P](=O)([O-])(OC[C@H](N)[C@H](O)\C=C\CCCCCCCCCCCCC)OCC[N+](C)(C)C
• InChI: 1S/C23H49N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4/h17-18,22-23,26H,5-16,19-21,24H2,1-4H3/b18-17+/t22-,23+/m0/s1
• InChI key: JLVSPVFPBBFMBE-HXSWCURESA-N

Description

General description

SPC is the deacylated derivative of sphingomyelin known to accumulate in neuropathic Niemann-Pick disease type A. A potent mitogen that increases intracellular free Ca²⁺ and free arachidonate through pathways that are only partially PKC-dependent. Stimulates DNA-binding activity of the transcription activator protein AP-1. Rapidly induces tyrosine phosphorylation of focal adhesion kinase (p125^FAK) and paxillin and causes a rapid and transient activation of MAP kinase in Swiss/3T3 cells. Also induces a unique reorganization of the actin cytoskeleton.

SPC is the deacylated derivative of sphingomyelin known to accumulate in neuropathic Niemann-Pick disease type A. A potent mitogen that increases intracellular free Ca²⁺ and free arachidonate through pathways that are only partially PKC-dependent. Stimulates DNA-binding activity of the transcription activator protein AP-1. Rapidly induces tyrosine phosphorylation of focal adhesion kinase (p125^FAK) and paxillin and causes a rapid and transient activation of MAP kinase in Swiss 3T3 cells. Also induces a unique reorganization of the actin cytoskeleton.

Biochem/physiol Actions

Cell permeable: no

Primary Target
A potent mitogen

Product does not compete with ATP.

Reversible: no

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following initial thaw, aliquot and freeze (-20°C). Stock solutions are stable for up to 2 months at -20°C.

Other Notes

Berger, A., et al. 1995. Proc. Natl. Acad. Sci. USA 92, 5885.
Dettbarn, C., et al. 1995. Brain Res.669, 79.
Seufferlein, T. and Rozengurt, E. 1995. J. Biol. Chem. 270, 24343.
Seufferlein, T. and Rozengurt, E. 1995. J. Biol. Chem. 270, 24334.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable