A PKC activator
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Phorbol 12-myristate 13-acetate

Item No. 10008014

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
tetradecanoic acid, (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1H-cyclopropa[3,4]benz[1,2-e]azulen-9-yl ester
CAS Number
16561-29-8
Synonyms
  • PMA
  • 12-O-Tetradecanoylphorbol-13-acetate
  • TPA
Molecular Formula
C36H56O8
Formula Weight
616.8
Purity
≥95%
Formulation
A solid
SMILES
O=C(CCCCCCCCCCCCC)O[C@H]1[C@](C2(C)C)(OC(C)=O)[C@]2([H])[C@@](C=C(CO)C[C@@]3(O)[C@@]4([H])C=C(C)C3=O)([H])[C@]4(O)[C@@H]1C
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Phorbol 12-myristate 13-acetate (PMA), also known as 12-O-tetradecanoylphorbol 13-acetate (TPA), is a phorbol ester and PKC activator.1,2,3,4,5 It activates the PKC isoforms PKCα, -β, -γ, -δ, -ε, -η, and -θ but not PKCζ or -ι/λ.2 PMA (1-10 ng/ml) induces NF-κB-dependent gene expression in a reporter assay.3 It promotes the differentiation of THP-1 monocytes into pro-inflammatory macrophages, as well as induces the formation of neutrophil extracellular traps (NETs), in vitro.4,5 PMA, in combination with 7,12-dimethylbenz[a]anthracene (DMBA; Item No. 30383), promotes papilloma formation in a rat two-stage model of skin carcinogenesis.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Goel, G., Makkar, H.P.S., Francis, G., et al. Phorbol esters: Structure, biological activity, and toxicity in animals. Int. J. Toxicol. 26(4), 279-288 (2007).

    2. Steinberg, S.F. Structural basis of protein kinase C isoform function. Physiol. Rev. 88(4), 1341-1378 (2008).

    3. Hellweg, C.E., Arenz, A., Bogner, S., et al. Activation of nuclear factor κB by different agents: Influence of culture conditions in a cell-based assay. Ann. N. Y. Acad. Sci. 1091, 191-204 (2006).

    4. Lund, M.E., To, J., O'Brien, B.A., et al. The choice of phorbol 12-myristate 13-acetate differentiation protocol influences the response of THP-1 macrophages to a pro-inflammatory stimulus. J. Immunol. Methods 430, 64-70 (2016).

    5. Petretto, A., Bruschi, M., Pratesi, F., et al. Neutrophil extracellular traps (NET) induced by different stimuli: A comparative proteomic analysis. PLoS One 14(7), e0218946 (2019).

    6. Vähätupa, M., Pemmari, T., Junttila, I., et al. Chemical-Induced Skin Carcinogenesis Model Using Dimethylbenz[a]Anthracene and 12-O-Tetradecanoyl Phorbol-13-Acetate (DMBA-TPA). J. Vis. Exp. 154 (2019).

    Product Citations

    Valbuena Perez, J.V., Linnenberger, R., Dembek, A., et al. Altered glucocorticoid metabolism represents a feature of macroph-aging. Aging Cell 19(6), e13156 (2020).

    Ghergurovich, J.M., García-Cañaveras, J.C., Wang, J., et al. A small molecule G6PD inhibitor reveals immune dependence on pentose phosphate pathway. Nat. Chem. Biol. 16(7), 731-739 (2020).

    Xu, S., Liu, B., Yin, M., et al. A novel TRPV4-specific agonist inhibits monocyte adhesion and atherosclerosis. Oncotarget 7(25), 37622-37635 (2016).