524400
Phorbol-12-myristate-13-acetate
Phorbol-12-myristate-13-acetate, CAS 16561-29-8, is the most common phorbol ester. Activates PKC at nanomolar concentrations.
Synonym(s):
Phorbol-12-myristate-13-acetate, PMA, TPA, PKC Activator I, TPA, PMA, PKC Activator I
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About This Item
Empirical Formula (Hill Notation):
C36H56O8
CAS Number:
Molecular Weight:
616.83
MDL number:
UNSPSC Code:
12352211
Recommended Products
Quality Level
Assay
≥98% (HPLC)
form
solid
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze
color
white
solubility
DMSO: 10 mg/mL
shipped in
ambient
storage temp.
−20°C
InChI
1S/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30-,32-,34-,35-,36-/m1/s1
InChI key
PHEDXBVPIONUQT-RGYGYFBISA-N
General description
Extremely potent mouse skin tumor promoter. Activates protein kinase C (PKC) in vivo and in vitro, even at nanomolar concentrations. Promotes the expression of iNOS in cultured hepatocytes. Activates Ca2+-ATPase and potentiates forskolin-induced cAMP formation. Inhibits apoptosis induced by the Fas antigen, but induces apoptosis in HL-60 promyelocytic leukemia cells. Most commonly used phorbol ester.
Most commonly-used phorbol ester. Extremely potent mouse skin tumor promoter. Activates protein kinase C in vivo and in vitro, even at nM concentrations. Promotes the expression of inducible NOS in cultured hepatocytes. Activates Ca2+-ATPase and potentiates forskolin-induced cAMP formation. Inhibits apoptosis induced by the Fas antigen, but induces apoptosis in HL-60 promyelocytic leukemia cells. Its binding is reversible. Also available as a 10 mM solution in DMSO (Cat. No. 500582).
Biochem/physiol Actions
Cell permeable: no
Primary Target
Protein Kinase C
Protein Kinase C
Product does not compete with ATP.
Reversible: yes
Packaging
Packaged under inert gas
Warning
Toxicity: Harmful (C)
Preparation Note
Further dilute with aqueous buffers just prior to use.
Reconstitution
Following reconstitution, aliquot and freeze (-20°C). Anhydrous DMSO stock solutions are stable for up to 6 months at -20°C. With frequent use, the DMSO stock solutions may accumulate water. The presence of water in the stock solution will accelerate the decomposition of the product, resulting in significant loss of activity in 2-3 months.
Other Notes
Powell, D.J., et al. 2003. Mol. Cell Biol.23, 7794.
Tepper, C.G., et al. 1995. Proc. Natl. Acad. Sci. USA92, 8443.
Oishi, K., and Yamaguchi, M. 1994. J. Cell. Biochem. 55, 168.
Macfarlane, D.E., and O’Donnell, P.S. 1993. Leukemia7, 1846.
Ghandi, V.C. and Jones, D.J., 1992. Neuropharmacol.31, 1101.
Hortelano, S., et al. 1992. J. Biol. Chem. 267, 24937.
Kontny, E., et al. 1992. Eur. J. Pharmacol.227, 333.
Zanaboni, P.B., et al. 1992. J. Appl. Physiol.73, 2011.
Saltis, J., et al. 1991. J. Biol. Chem.266, 261.
Beguinot, L., et al. 1985. Proc. Natl. Acad. Sci. USA82, 2774.
Perchellet, J. 1985. Carcinogenesis6, 567.
Nishizuka, Y. 1984. Science255, 1365.
Mastro, A. 1982. Lymphokines6, 263.
Tepper, C.G., et al. 1995. Proc. Natl. Acad. Sci. USA92, 8443.
Oishi, K., and Yamaguchi, M. 1994. J. Cell. Biochem. 55, 168.
Macfarlane, D.E., and O’Donnell, P.S. 1993. Leukemia7, 1846.
Ghandi, V.C. and Jones, D.J., 1992. Neuropharmacol.31, 1101.
Hortelano, S., et al. 1992. J. Biol. Chem. 267, 24937.
Kontny, E., et al. 1992. Eur. J. Pharmacol.227, 333.
Zanaboni, P.B., et al. 1992. J. Appl. Physiol.73, 2011.
Saltis, J., et al. 1991. J. Biol. Chem.266, 261.
Beguinot, L., et al. 1985. Proc. Natl. Acad. Sci. USA82, 2774.
Perchellet, J. 1985. Carcinogenesis6, 567.
Nishizuka, Y. 1984. Science255, 1365.
Mastro, A. 1982. Lymphokines6, 263.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 1 Dermal - Acute Tox. 1 Inhalation - Acute Tox. 2 Oral - Carc. 2 - Eye Dam. 1 - Resp. Sens. 1 - Skin Corr. 1B - Skin Sens. 1
Storage Class Code
6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials
WGK
WGK 3
Certificates of Analysis (COA)
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