Description
Phorbol 12-myristate-13-acetate (16561-29-8) activates protein kinase C (10-100 ng/ml)1. May display PKC-independent effects in various cell types2. Warning: Phorbol 12-myristate-13-acetate is a skin irritant. Avoid contact with this compound.
Chemical Properties
white to off-white solid
Uses
4β-Phorbol 12-Myristate 13-Acetate is used in the activation of certain pyruvate kinases as well as protein kinases.
Definition
ChEBI: Phorbol 13-acetate 12-myristate is a phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types. It has a role as a protein kinase C agonist, an antineoplastic agent, a reactive oxygen species generator, a plant metabolite, a mitogen, a carcinogenic agent and an apoptosis inducer. It is an acetate ester, a tetradecanoate ester, a diester, a tertiary alpha-hydroxy ketone and a phorbol ester.
General Description
White crystals.
Air & Water Reactions
Practically water insoluble.
Reactivity Profile
PHORBOL 12-MYRISTATE 13-ACETATE is sensitive to acids and alkalis. .
Fire Hazard
Flash point data for PHORBOL 12-MYRISTATE 13-ACETATE are not available; however, PHORBOL 12-MYRISTATE 13-ACETATE is probably combustible.
Biological Activity
Extensively used phorbol ester activator of protein kinase C; tumor promoter. Binds to PKC with a K i value of 2.6 nM as measured by displacement of [ 3 H]phorbol 12,13-dibutyrate binding in rat cortex synaptosomal membranes.
Biochem/physiol Actions
Cell permeable: yes
storage
-20°C (protect from light)
References
1) Saraiva et al. (2004), Characterization of phorbol esters activity on individual mammalian protein kinase C isoforms, using the yeast phenotypic assay; Eur. J. Pharmacol., 491 101
2) Doerner et al. (1990), Protein kinase C-dependent and independent effects of phorbol esters on hippocampal calcium channel current; J. Neurosci., 10 1699
3) Merck Index 14:7332
