12-O-Tetradecanoylphorbol-13-acetate
 | |
| Names | |
|---|---|
| IUPAC name
(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetyloxy)-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl myristate | |
| Other names
TPA, PMA, Phorbol myristate acetate, Tetradecanoylphorbol acetate. | |
| Identifiers | |
16561-29-8  | |
| ChEMBL | ChEMBL279115  |
| ChemSpider | 25977 |
| |
| Jmol-3D images | Image Image |
| KEGG | C05151 |
| PubChem | 27924 |
| |
| Properties | |
| Molecular formula |
C36H56O8 |
| Molar mass | 616.83 g·mol−1 |
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| verify (what is: /?) | |
| Infobox references | |
12-O-Tetradecanoylphorbol-13-acetate (TPA), also commonly known as tetradecanoylphorbol acetate, tetradecanoyl phorbol acetate, and phorbol 12-myristate 13-acetate (PMA), is a diester of phorbol and a potent tumor promoter often employed in biomedical research to activate the signal transduction enzyme protein 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 a small molecule drug.
In ROS biology, superoxide, but not hydrogen peroxide, hydroxyl radical, peroxynitrite, was identified as the major ROS species induced by TPA/PMA but not by ionomycin in mouse macrophages.[4] Thus, TPA/PMA has been routinely used as an inducer for endogenous superoxide production. [5]
TPA is also being studied as a drug in the treatment of hematologic cancer.
TPA has a specific use in cancer diagnostics as a B-cell specific mitogen in cytogenetic testing. To view the chromosomes, a cytogenetic test requires dividing cells. TPA is used to stimulate division of B-cells during cytogenetic diagnosis of B-cell cancers such as chronic lymphocytic leukemia.[6]
TPA is also commonly used together with ionomycin to stimulate T-cell activation, proliferation, and cytokine production, and is used in protocols for intracellular staining of these cytokines.[7]
TPA was first found in the croton plant, a shrub found in Southeast Asia, exposure to which provokes a poison ivy-like rash. It underwent a phase 1 clinical trial.
References
- ↑ Castagna et al. (1982). Journal of Biological Chemistry 257 (13): 7847–7851.
- ↑ Blumberg (1988). Cancer Research 48: 1–8.
- ↑ Niedel et al. (1983). "Phorbol Diester Receptor Copurifies with Protein Kinase C". Proceedings of the National Academy of Sciences 80: 36–40. doi:10.1073/pnas.80.1.36.
- ↑ Swindle (2002). The journal of Immunology 169: 5866–5873. .
- ↑ Huang (2014). PLOS ONE (journal) 9: e96246. .
- ↑ The AGT cytogenetics laboratory manual. 3rd ed. Barch, Margaret J., Knutsen, Turid., Spurbeck, Jack L., eds. 1997. Lippincott-Raven.
- ↑ "Flow Cytometry Intracellular Staining Guide". eBioscience, Inc. Retrieved 2011-09-25.
External links
- Tetradecanoylphorbol Acetate at the US National Library of Medicine Medical Subject Headings (MeSH)
- "NCI Dictionary Entry". Retrieved 2005-07-02.
- "Phase 1 Clinical Trials". Retrieved 2005-07-02.