559300

Safingol

A cell-permeable and reversible lyso-sphingolipid protein kinase C (PKC) inhibitor that competitively interacts at the regulatory phorbol binding domain of PKC.

• Synonym(s): Safingol, L- threo-Dihydrosphingosine
• Empirical Formula (Hill Notation): C₁₈H₃₉NO₂
• CAS Number: 15639-50-6
• Molecular Weight: 301.51
• MDL number: MFCD00792847
• UNSPSC Code: 12352200

Properties

• Quality Level: 100
• assay: ≥98% (TLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: white
• solubility: ethanol: 10 mg/mL; DMSO: 5 mg/mL; methanol: 5 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• InChI: 1S/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3
• InChI key: OTKJDMGTUTTYMP-UHFFFAOYSA-N

Description

General description

A cell-permeable and reversible lyso-sphingolipid protein kinase C (PKC) inhibitor that competitively interacts at the regulatory phorbol binding domain of PKC. Inhibits enzymatic activity and ³H-phorbol dibutyrate binding of purified rat brain PKC (IC₅₀ = 37.5 µM and 31 µM, respectively). Inhibits human PKC_α, the major overexpressed isoenzyme in MCF-7 DOXR cells (IC₅₀ = 40 µM). Enhances the cytotoxic effect of the chemotherapeutic agent Mitomycin C (MMC; Cat. Nos. 47589 and 475820) in gastric cancer cells by promoting drug-induced apoptosis.

A cell-permeable and reversible lyso-sphingolipid protein kinase C (PKC) inhibitor that competitively interacts at the regulatory phorbol binding domain of PKC. Inhibits enzymatic activity and ³H-phorbol dibutyrate binding of purified rat brain PKC (IC₅₀ = 37.5 µM and 31 µM, respectively). Inhibits human PKC_α, the major overexpressed isoenzyme in MCF-7 DOXR cells (IC₅₀ = 40 µM). Enhances the cytotoxic effect of the chemotherapeutic agent mitomycin C (MMC; Cat. No. 47589) in gastric cancer cells by promoting drug-induced apoptosis.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
Enzymatic activity and 3H-phorbol dibutyrate binding of purified rat brain PKC

Product does not compete with ATP.

Reversible: yes

Target IC₅₀: 37.5 µM and 31 µM, inhibiting enzymatic activity and 3H-phorbol dibutyrate binding of purified rat brain PKC, respectively

Warning

Toxicity: Irritant (B)

Reconstitution

Following initial thaw, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Kedderis, L.B., et al. 1995. Fundam. Appl. Toxicol.25, 201.
Sachs, C.W., et al. 1995. J. Biol. Chem. 270, 26639.
Schwartz, G.K., et al. 1995. J. Natl. Cancer Inst.87,1394.

Legal Information

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable