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| Names | |
|---|---|
| Preferred IUPAC name (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b-Dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-9aH-cyclopropa[3,4]benzo[1,2-e]azulene-9,9a-diyl 9a-acetate 9-tetradecanoate | |
| Other names TPA, PMA, Phorbol myristate acetate, Tetradecanoylphorbol acetate. | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.109.485 |
| KEGG |
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| UNII | |
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| Properties | |
| C36H56O8 | |
| Molar mass | 616.83 g/mol |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
12-O-Tetradecanoylphorbol-13-acetate (TPA), also commonly known astetradecanoylphorbol acetate,tetradecanoyl phorbol acetate, andphorbol 12-myristate 13-acetate (PMA) is a diester ofphorbol. It is a potenttumor promoter often employed in biomedical research to activate thesignal transductionenzymeprotein kinase C (PKC).[1][2][3] The effects of TPA on PKC result from its similarity to one of the natural activators of classic PKC isoforms,diacylglycerol. TPA is asmall molecule drug.
InROS biology,superoxide was identified as the major reactive oxygen species induced by TPA/PMA but not byionomycin in mouse macrophages.[4] Thus, TPA/PMA has been routinely used as an inducer for endogenoussuperoxide production.[5]
TPA is also being studied as adrug in the treatment ofhematologiccancer[citation needed]
TPA has a specific use in cancer diagnostics as a B-cell specificmitogen incytogenetic testing. Cells must be divided in a cytogenic test to view the chromosomes. TPA is used to stimulate division of B-cells during cytogenetic diagnosis of B-cell cancers such aschronic lymphocytic leukemia.[6]
TPA is also commonly used together withionomycin to stimulate T-cell activation, proliferation, and cytokine production, and is used in protocols for intracellular staining of these cytokines.[7]
TPA inducesKSHV reactivation in PEL cell cultures via stimulation of the mitogen-activated protein kinase (MAPK)/extracellular signal-regulated kinase (ERK) pathway. The pathway involves the activation of the early-immediate viral protein RTA that contributes to the activation of the lytic cycle.[8]
TPA was first found in theCroton plant, a shrub found in Southeast Asia, exposure to which provokes apoison ivy-like rash.[citation needed] It underwent a phase 1clinical trial.[9]
