12-O-Tetradecanoylphorbol-13-acetate

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
CAS Number	16561-29-8
ChEBI	CHEBI:37537
ChEMBL	ChEMBL279115
ChemSpider	25977
IUPHAR/BPS	2341
Jmol 3D model	Interactive image Interactive image
KEGG	C05151
PubChem	27924
InChI 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 Key: PHEDXBVPIONUQT-RGYGYFBISA-N InChI=1/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 Key: PHEDXBVPIONUQT-RGYGYFBIBK
SMILES CCCCCCCCCCCCCC(=O)O[C@@H]1[C@H]([C@]2([C@@H](C=C(C[C@]3([C@H]2C=C(C3=O)C)O)CO)[C@H]4[C@@]1(C4(C)C)OC(=O)C)O)C CCCCCCCCCCCCCC(=O)O[C@@H]2C(C)[C@]1(O)C4/C=C(/C)C(=O)[C@@]4(O)CC(\CO)=C/[C@H]1[C@H]3[C@]2(OC(C)=O)C3(C)C
Properties
Chemical formula	C36H56O8
Molar mass	616.83 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

1. Castagna; et al. (1982). Journal of Biological Chemistry 257 (13): 7847–7851.
2. Blumberg (1988). Cancer Research 48: 1–8.
3. 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.
4. Swindle (2002). The journal of Immunology 169: 5866–5873..
5. Huang (2014). PLOS ONE (journal) 9: e96246..
6. The AGT cytogenetics laboratory manual. 3rd ed. Barch, Margaret J., Knutsen, Turid., Spurbeck, Jack L., eds. 1997. Lippincott-Raven.
7. "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.