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Submit ReviewPhorbol 12-myristate 13-acetate
Description: Protein kinase C activator
Alternative Names: PMA
Chemical Name: (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 tetradecanoate
Purity: ≥98% (HPLC)
Biological Activity for Phorbol 12-myristate 13-acetate
Phorbol 12-myristate 13-acetate is an extensively used phorbol ester high affinity activator of protein kinase C (Ki = 2.6 nM as measured by displacement of [3H]phorbol 12,13-dibutyrate binding in rat cortex synaptosomal membranes). It binds to the C1a and C1b domains of PKC inducing membrane translocation of PKC. Phorbol 12-myristate 13-acetate activates the PKC isoforms PKCα, -β, -γ, -δ, -ε, -η, and -θ but not PKCζ or -ι/λ. Phorbol 12-myristate 13-acetate is a tumor promoter. Phorbol 12-myristate 13-acetate can also induce differentiation of THP-1 monocytes to a macrophage phenotype in vitro.
Technical Data for Phorbol 12-myristate 13-acetate
| M. Wt | 616.83 |
| Formula | C36H56O8 |
| Storage | Store at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 16561-29-8 |
| PubChem ID | 27924 |
| InChI Key | PHEDXBVPIONUQT-RGYGYFBISA-N |
| Smiles | OCC1=C[C@]([C@@](C(C)4C)([H])[C@@]4(OC(C)=O)[C@H](OC(CCCCCCCCCCCCC)=O)[C@H]3C)([H])[C@@]3(O)[C@@](C=C(C)C2=O)([H])[C@]2(O)C1 |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for Phorbol 12-myristate 13-acetate
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 61.68 | 100 |
Preparing Stock Solutions for Phorbol 12-myristate 13-acetate
The following data is based on the product molecular weight 616.83. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.62 mL | 8.11 mL | 16.21 mL |
| 5 mM | 0.32 mL | 1.62 mL | 3.24 mL |
| 10 mM | 0.16 mL | 0.81 mL | 1.62 mL |
| 50 mM | 0.03 mL | 0.16 mL | 0.32 mL |
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Product Datasheets for Phorbol 12-myristate 13-acetate
References for Phorbol 12-myristate 13-acetate
References are publications that support the biological activity of the product.
Castagna et al (1982) Direct activation of calcium-activated, phospholipid-dependent protein kinase by tumor-promoting phorbol esters. J.Biol.Chem. 257 7847 PMID: 7085651
Hockberger et al (1989) A diacylglycerol analogue reduces neuronal calcium currents independently of protein kinase C activation. Nature 338 340 PMID: 2922062
Murphy et al (1999) Structural determinants of phorbol ester binding in synaptosomes: pharmacokinetics and pharmacodynamics. Eur.J.Pharmacol. 381 77 PMID: 10528137
Merck Index 12 7487
Steinberg (2008) Structural basis of protein kinase C isoform function. Physiol.Rev. 88 1341 PMID: 18923184
Lund et al (2016) 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 PMID: 26826276
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Keywords: Phorbol 12-myristate 13-acetate, Phorbol 12-myristate 13-acetate supplier, Protein, kinases, C, activators, PKC, Phorbol12-myristate13-acetate, PMA, Kinase, 1201, Tocris Bioscience
28 Citations for Phorbol 12-myristate 13-acetate
Citations are publications that use Tocris products. Selected citations for Phorbol 12-myristate 13-acetate include:
Brust et al (2015) New functional activity of aripipr. revealed: Robust antagonism of D2 DA receptor-stimulated Gβγ signaling. J Vis Exp 93 85 PMID: 25449598
Li et al (2014) PMA induces SnoN proteolysis and CD61 expression through an autocrine mechanism. Cell Signal 26 1369 PMID: 24637302
Baba et al (2013) Heteromeric MT1/MT2 melatonin receptors modulate photoreceptor function. Sci Signal 6 ra89 PMID: 24106342
Gabriel et al (2012) The acid-sensitive, anesthetic-activated potassium leak channel, KCNK3, is regulated by 14-3-3β-dependent, protein kinase C (PKC)-mediated endocytic trafficking. J Biol Chem 287 32354 PMID: 22846993
Arnold et al (2018) Hypertension-evoked RhoA activity in vascular smooth muscle cells requires RGS5. FASEB J 32 2021 PMID: 29208700
Schaffer et al (2018) PKCε Inhibits Neuronal Dendritic Spine Development through Dual Phosphorylation of Ephexin5. Cell Rep 25 2470 PMID: 30485813
Cicero et al (2016) A High Throughput Phenotypic Screening reveals compounds that counteract premature osteogenic differentiation of HGPS iPS-derived mesenchymal stem cells. Sci Rep 6 34798 PMID: 27739443
Quizon (2016) Molecular mechanism: the human DA transporter histidine 547 regulates basal and HIV-1 Tatprotein-inhibited DA transport. Scientific Reports 6 39048 PMID: 27966610
Bohnekamp et al (2010) Involvement of the chemokine-like receptor GPR33 in innate immunity. Br J Pharmacol 396 272 PMID: 20399748
Liu et al (2018) Developmental protein kinase C hyper-activation results in microcephaly and behavioral abnormalities in zebrafish. Transl Psychiatry 8 232 PMID: 30352990
Kaszás et al (2012) Small molecule positive allosteric modulation of TRPV1 activation by vanilloids and acidic pH. J Neurosci 340 152 PMID: 22005042
Gao et al (2012) Transient receptor potential vanilloid type 1-dependent regulation of liver-related neurons in the paraventricular nucleus of the hypothalamus diminished in the type 1 diabetic mouse. J Virol 61 1381 PMID: 22492526
Zsombok et al (2011) Functional plasticity of central TRPV1 receptors in brainstem dorsal vagal complex circuits of streptozotocin-treated hyperglycemic mice. Curr Alzheimer Res 31 14024 PMID: 21957263
Hagen et al (2015) Comparative Multi-Donor Study of IFNγ Secretion and Expression by Human PBMCs Using ELISPOT Side-by-Side with ELISA and Flow Cytometry Assays. Cells 4 84 PMID: 25679284
Bemben et al (2015) Autism-associated mutation inhibits protein kinase C-mediated neuroligin-4X enhancement of excitatory synapses. Proc Natl Acad Sci U S A 112 2551 PMID: 25675530
Walsh et al (2014) The role of Nox1 and Nox2 in GPVI-dependent platelet activation and thrombus formation. Redox Biol 2 178 PMID: 24494191
Yu et al (2014) Transactivation of epidermal growth factor receptor through platelet-activating factor/receptor in ovarian cancer cells. J Exp Clin Cancer Res 33 85 PMID: 25261977
Specht et al (2011) Regulation of glycine receptor diffusion properties and gephyrin interactions by protein kinase C. EMBO J 30 3842 PMID: 21829170
Navaroli et al (2011) The plasma membrane-associated GTPase Rin interacts with the DA transporter and is required for protein kinase C-regulated DA transporter trafficking. J Neurosci 31 13758 PMID: 21957239
Davis (2015) The ATP-Binding Cassette Transporter-2 (ABCA2) Overexpression Modulates Sphingosine Levels and Transcription of the Amyloid Precursor Protein (APP) Gene. Biochem Pharmacol 12 847 PMID: 26510981
Brown et al (2014) Mitogen-activated protein kinase-interacting kinase regulates mTOR/AKT signaling and controls the serine/arginine-rich protein kinase-responsive type 1 internal ribosome entry site-mediated translation and viral oncolysis. J Pharmacol Exp Ther 88 13149 PMID: 25187540
Nishida et al (2009) Inhibition of ATR protein kinase activity by schisandrin B in DNA damage response. Nucleic Acids Res 37 5678 PMID: 19625493
Mestre et al (2019) Manipulation of Gut Microbiota Influences Immune Responses, Axon Preservation, and Motor Disability in a Model of Progressive Multiple Sclerosis. Front Immunol 10 1374 PMID: 31258540
Tasoglu et al (2015) Levitational Image Cytometry with Temporal Resolution. Adv Mater 27 3901 PMID: 26058598
Sakata et al (2012) Glucose-mediated control of ghrelin release from primary cultures of gastric mucosal cells. Am J Physiol Endocrinol Metab 302 E1300 PMID: 22414807
Kapfhammer and Gugger (2012) The analysis of purkinje cell dendritic morphology in organotypic slice cultures. J Biol Chem NULL PMID: 22473312
Hirasawa (2003) Nifedipine facilitates neurotransmitter release independently of calcium channels. Proc Natl Acad Sci U S A 100 6139 PMID: 12714685
Jones et al (2004) Regulation of SHP-1 tyrosine phosphatase in human platelets by serine phosphorylation at its C terminus. Biochem Biophys Res Commun 279 40475 PMID: 15269224
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Reviews for Phorbol 12-myristate 13-acetate
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Action of phorbol 12-myristate 13-acetate in neutrophils.
By
Sergiy Sylantyev on 07/13/2023
Assay Type: In Vitro
Species: Human
Cell Line/Tissue: Blood
Phorbol 12-myristate 13-acetate (PMA) was used to quantify the input of PKC into Ca2+ concentration fluctuations in human neutrophils. Figure: PMA effect on the Ca2+ - induced fluorescence in a single neutrophil (right column).
human isolate PBMCs.
By
Tahmineh Safaie on 08/04/2020
Assay Type: In Vitro
Species: Human
Cell Line/Tissue: PBMC
human isolate PBMCs were stimulate with 50 ng/ml of PMA for 24 hours and IFN-g secretion was measured with ELISA
