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524400

Sigma-Aldrich

Phorbol-12-myristate-13-acetate - CAS 16561-29-8 - Calbiochem

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 - CAS 16561-29-8 - Calbiochem, PMA, TPA, PKC Activator I, TPA, PMA, PKC Activator I
Empirical Formula (Hill Notation):
C36H56O8
CAS Number:
Molecular Weight:
616.83
MDL number:

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).

Packaging

1, 5, 10, 25 mg in Glass bottle
Packaged under inert gas

Biochem/physiol Actions

Product does not compete with ATP.
Cell permeable: no
Reversible: yes
Primary Target
Protein Kinase C

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.

Legal Information

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

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 1 Inhalation - Acute Tox. 2 Oral - Carc. 2 - Eye Dam. 1 - Skin Irrit. 2

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

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