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P8139 Sigma

Phorbol 12-myristate 13-acetate

≥99% (TLC), film or powder

Synonym: 12-O-Tetradecanoylphorbol 13-acetate, 4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate, PMA, TPA

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cancer Research, Cell Biology, Cell Signaling and Neuroscience,
assay   ≥99% (TLC)
form   film or powder
solubility   DMSO: soluble (Dissolve in water-miscible organic solvent prior to preparing aqueous solutions. DMSO solutions can be stored dark at -20 °C for at least six months.)
  ethanol: soluble (Dissolve in water-miscible organic solvent prior to preparing aqueous solutions.)
storage temp.   −20°C

Description

Frequently Asked Questions

Live Chat and Frequently Asked Questions are available for this Product.

Biochem/physiol Actions

Potent tumor promoter; activates protein kinase C in vivo and in vitro.

Caution

Photosensitive

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®,1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

This compound is featured on the PKC page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Price and Availability

Suggested Laboratory Gloves


Laboratory GlovesThis substance has been tested against several types of hand protection for CE compliance. Click below to find the recommended gloves for handling this product.




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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
WGK Germany 
3
RTECS 
QH4377000

Protocols & Articles

Articles

Carcinogenesis and Epigenetics

Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete. The expansion of the carcinogenesi...
Vicki Caligur
BioFiles 2008, 3.5, 18.
Keywords: Acetylations, Adhesion, Alkylations, Apoptosis, Biofiles, Cancer, Carcinogens, Cell division, Cell proliferation, Cell signaling, DNA microarrays, Drug discovery, Environmental, Epigenetics, Events, Gene expression, Genetic, Hormones, Metabolism, Methylations, Microarray Analysis, Mutagens, PAGE, Recombination, Reductions, Sequences, Transcription, Type, transformation

Peer-Reviewed Papers

References

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Tat-biliverdin reductase A inhibits inflammatory response by regulation of MAPK and NF-κB pathways in Raw 264.7 cells and edema mouse model. Kim HR, Kim DW, Jo HS, et al. Mol. Immunol. 63(2), 355-66, (2015)

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A functional transient receptor potential vanilloid 4 (TRPV4) channel is expressed in human endothelial progenitor cells. Dragoni S, Guerra G, Fiorio Pla A, et al. J. Cell Physiol. 230(1), 95-104, (2015)

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Differential 12-O-Tetradecanoylphorbol-13-acetate-induced activation of rat mammary carcinoma susceptibility Fbxo10 variant promoters via a PKC-AP1 pathway. Xu X, Prough RA, and Samuelson DJ Mol. Carcinog. 54(2), 134-47, (2015)

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Effect of short-term hyperglycemia on protein kinase C alpha activation in human erythrocytes. Livshits L, Srulevich A, Raz I, et al. Rev. Diabet. Stud. 9(2-3), 94-103, (2012)

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Geraniol attenuates 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced oxidative stress and inflammation in mouse skin: possible role of p38 MAP Kinase and NF-κB. Khan AQ, Khan R, Qamar W, et al. Exp. Mol. Pathol. 94(3), 419-29, (2013)

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ADAM10 is the major sheddase responsible for the release of membrane-associated meprin A. Herzog C, Haun RS, Ludwig A, et al. J. Biol. Chem. 289(19), 13308-22, (2014)

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Phosphorylation of Noxo1 at threonine 341 regulates its interaction with Noxa1 and the superoxide-producing activity of Nox1. Yamamoto A, Takeya R, Matsumoto M, et al. FEBS J. 280(20), 5145-59, (2013)

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Upregulation of membrane-bound CD40L on CD4+ T cells in women with primary Sjögren's syndrome. Belkhir R, Gestermann N, Koutero M, et al. Scand. J. Immunol. 79(1), 37-42, (2014)

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Monoubiquitination of filamin B regulates vascular endothelial growth factor-mediated trafficking of histone deacetylase 7. Su YT, Gao C, Liu Y, et al. Mol. Cell. Biol. 33(8), 1546-60, (2013)

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Isolation of cytotoxic metabolites from targeted peruvian amazonian medicinal plants. José C Aponte et al J. Nat. Prod. 71, 102-5, (2008)

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Conformationally constrained analogues of diacylglycerol (DAG). 27. Modulation of membrane translocation of protein kinase C (PKC) isozymes alpha and delta by diacylglycerol lactones (DAG-lactones) containing rigid-rod acyl groups. Krishnan Malolanarasimhan et al J. Med. Chem. 50, 962-78, (2007)

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Selective inhibition of the function of tyrosine-phosphorylated STAT3 with a phosphorylation site-specific intrabody. Koo MY, Park J, Lim JM, et al. Proc. Natl. Acad. Sci. U. S. A. 111(17), 6269-74, (2014)

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Light-dependent translocation of arrestin in rod photoreceptors is signaled through a phospholipase C cascade and requires ATP. Orisme W Cell. Signal. 22(3), 447-56, (2010)

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Activation of PKCβII by PMA facilitates enhanced epithelial wound repair through increased cell spreading and migration. Sumagin R, Robin AZ, Nusrat A, et al. PLoS ONE 8(2), e55775, (2013)

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Thymoquinone inhibits phorbol ester-induced activation of NF-κB and expression of COX-2, and induces expression of cytoprotective enzymes in mouse skin in vivo. Kundu JK, Liu L, Shin JW, et al. Biochem. Biophys. Res. Commun. 438(4), 721-7, (2013)

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Restored circulating invariant NKT cells are associated with viral control in patients with chronic hepatitis B. Jiang X PLoS ONE 6(12), e28871, (2011)

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S100A9 has a protective role in inflammation-induced skin carcinogenesis. McNeill E and Hogg N Int. J. Cancer 135(4), 798-808, (2014)

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Astrocytic TGF-β signaling limits inflammation and reduces neuronal damage during central nervous system Toxoplasma infection. Cekanaviciute E, Dietrich HK, Axtell RC, et al. J. Immunol. 193(1), 139-49, (2014)

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Characterization of regulatory T cells identified as CD4(+)CD25(high)CD39(+) in patients with active tuberculosis. T Chiacchio et al Clin. Exp. Immunol. 156, 463-70, (2009)

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High glucose modulates IL-6 mediated immune homeostasis through impeding neutrophil extracellular trap formation. Joshi MB, Lad A, Bharath Prasad AS, et al. FEBS Lett. 587(14), 2241-6, (2013)

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The zebrafish ortholog of TRPV1 is required for heat-induced locomotion. Gau P, Poon J, Ufret-Vincenty C, et al. J. Neurosci. 33(12), 5249-60, (2013)

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Targeted activation of conventional and novel protein kinases C through differential translocation patterns. Hui X, Reither G, Kaestner L, et al. Mol. Cell. Biol. 34(13), 2370-81, (2014)

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Impact of mycophenolic acid on the functionality of human polymorphonuclear neutrophils and dendritic cells during interaction with Aspergillus fumigatus. Markus Mezger et al Antimicrob. Agents Chemother. 52, 2644-6, (2008)

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Nuclear factor κB mediates suppression of canonical transient receptor potential 6 expression by reactive oxygen species and protein kinase C in kidney cells. Wang Y, Ding M, Chaudhari S, et al. J. Biol. Chem. 288(18), 12852-65, (2013)

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The F-box protein FBXO25 promotes the proteasome-dependent degradation of ELK-1 protein. Teixeira FR, Manfiolli AO, Soares CS, et al. J. Biol. Chem. 288(39), 28152-62, (2013)

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Disruption of endothelial adherens junction by invasive breast cancer cells is mediated by reactive oxygen species and is attenuated by AHCC. Haidari M, Zhang W, and Wakame K Life Sci. 93(25-26), 994-1003, (2013)

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Altered prostanoid signaling contributes to increased skin tumorigenesis in Tpl2 knockout mice. DeCicco-Skinner KL, Nolan SJ, Deshpande MM, et al. PLoS ONE 8(2), e56212, (2013)

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Synthesis and biological evaluation of 12-aminoacylphorboids. Alberto Pagani et al J. Nat. Prod. 73, 447-51, (2010)

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Nanog expression is negatively regulated by protein kinase C activities in human cancer cell lines. Chu WK, Dai PM, Li HL, et al. Carcinogenesis 34(7), 1497-509, (2013)

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Impaired infectivity of ritonavir-resistant HIV is rescued by heat shock protein 90AB1. Joshi P J. Biol. Chem. 286(28), 24581-92, (2011)

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A keratin 15 containing stem cell population from the hair follicle contributes to squamous papilloma development in the mouse. Li S, Park H, Trempus CS, et al. Mol. Carcinog. 52(10), 751-9, (2013)

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Chemopreventive effect of sarcophine-diol on NOR-1-induced TPA-promoted skin carcinogenesis in female HOS:HR-1 mice. Szymanski PT, Ahmed SA, Khalifa S, et al. Nat. Prod. Commun. 8(2), 153-4, (2013)

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Isolation of new phenylacetylingol derivatives that reactivate HIV-1 latency and a novel spirotriterpenoid from Euphorbia officinarum latex. Mourad Daoubi et al Bioorg. Med. Chem. 15, 4577-84, (2007)

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A new flow cytometry method to measure oxidative status: the Peroxidation of Leukocytes Index Ratio (PLIR). Peluso I, Adorno G, Raguzzini A, et al. J. Immunol. Methods 390(1-2), 113-20, (2013)

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High-level fluorescence labeling of gram-positive pathogens. Aymanns S PLoS ONE 6(6), e19822, (2011)

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Macrophage migration inhibitory factor triggers chemotaxis of CD74+CXCR2+ NKT cells in chemically induced IFN-γ-mediated skin inflammation. Hsieh CY, Chen CL, Lin YS, et al. J. Immunol. 193(7), 3693-703, (2014)

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Human choroid plexus papilloma cells efficiently transport glucose and vitamin C. Ulloa V, García-Robles M, Martínez F, et al. J. Neurochem. 127(3), 403-14, (2013)

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The COP II adaptor protein TMED7 is required to initiate and mediate the delivery of TLR4 to the plasma membrane. Liaunardy-Jopeace A, Bryant CE, and Gay NJ Sci. Signal. 7(336), ra70, (2014)

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β-Arrestin1 and distinct CXCR4 structures are required for stromal derived factor-1 to downregulate CXCR4 cell-surface levels in neuroblastoma. Clift IC, Bamidele AO, Rodriguez-Ramirez C, et al. Mol. Pharmacol. 85(4), 542-52, (2014)

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TSPAN33 is a novel marker of activated and malignant B cells. Luu VP, Hevezi P, Vences-Catalan F, et al. Clin. Immunol. 149(3), 388-99, (2013)

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Tumor promoter-induced sulfiredoxin is required for mouse skin tumorigenesis. Wu L, Jiang H, Chawsheen HA, et al. Carcinogenesis 35(5), 1177-84, (2014)

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Transient receptor potential ankyrin-1 (TRPA1) modulates store-operated Ca(2+) entry by regulation of STIM1-Orai1 association. Albarrán L, Lopez JJ, Dionisio N, et al. Biochim. Biophys. Acta 1833(12), 3025-34, (2013)

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PMA withdrawal in PMA-treated monocytic THP-1 cells and subsequent retinoic acid stimulation, modulate induction of apoptosis and appearance of dendritic cells. Spano A, Barni S, and Sciola L Cell Prolif. 46(3), 328-47, (2013)

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Slit2 promotes tumor growth and invasion in chemically induced skin carcinogenesis. Qi C, Lan H, Ye J, et al. Lab. Invest. 94(7), 766-76, (2014)

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Accelerated receptor shedding inhibits kidney injury molecule-1 (KIM-1)-mediated efferocytosis. Gandhi R, Yi J, Ha J, et al. Am. J. Physiol. Renal Physiol. 307(2), F205-21, (2014)

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HDAC inhibitors prevent the induction of the immediate-early gene FOSL1, but do not alter the nucleosome response. Khan DH and Davie JR FEBS Lett. 587(10), 1510-7, (2013)

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The effects of dissociated glucocorticoids RU24858 and RU24782 on TPA-induced skin tumor promotion biomarkers in SENCAR mice. Kowalczyk P, Junco JJ, Kowalczyk MC, et al. Mol. Carcinog. 53(6), 488-97, (2014)

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Do β-cells generate peroxynitrite in response to cytokine treatment? Broniowska KA, Mathews CE, and Corbett JA J. Biol. Chem. 288(51), 36567-78, (2013)

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Protein kinase C-activating tumor promoters modulate the DNA damage response in UVC-irradiated TK6 cells. Glover KP, Markell LK, Donner EM, et al. Toxicol. Lett. 229(1), 210-9, (2014)

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Annexin A3 plays a role in cytoplasmic calcium oscillation by extracellular calcium in the human promyelocytic leukemia HL-60 cells differentiated by phorbol-12-myristate-13-acetate. Nishiura H, Yamanegi K, Kawabe M, et al. Exp. Mol. Pathol. 97(2), 241-6, (2014)

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Ritonavir binds to and downregulates estrogen receptors: molecular mechanism of promoting early atherosclerosis. Xiang J, Wang Y, Su K, et al. Exp. Cell Res. 327(2), 318-30, (2014)

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Evaluation of T cell responses in healing and nonhealing leishmaniasis reveals differences in T helper cell polarization ex vivo and in vitro. Choi BS Parasite Immunol. 31(4), 199-209, (2009)

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Protein kinase C restricts transport of carnitine by amino acid transporter ATB(0,+) apically localized in the blood-brain barrier. Michalec K, Mysiorek C, Kuntz M, et al. Arch. Biochem. Biophys. 554, 28-35, (2014)

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Tryptanthrin ameliorates atopic dermatitis through down-regulation of TSLP. Han NR, Moon PD, Kim HM, et al. Arch. Biochem. Biophys. 542, 14-20, (2014)

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Design and synthesis of protein kinase C? activators based on 'out of pocket' interactions. Go Hirai et al Bioorg. Med. Chem. Lett. 21, 3587-90, (2011)

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Acute promyelocytic leukemia mutated to radioresistance suppressed monocyte lineage differentiation by phorbol 12-myristate 13-acetate. Monzen S, Takimura K, Kashiwakura I, et al. Leuk. Res. 37(9), 1162-9, (2013)

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The zinc finger transcription factor ZXDC activates CCL2 gene expression by opposing BCL6-mediated repression. Ramsey JE and Fontes JD Mol. Immunol. 56(4), 768-80, (2013)

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Modulatory effects of Azadirachta indica leaf extract on cutaneous and hepatic biochemical status during promotion phase of DMBA/TPA-induced skin tumorigenesis in mice. Arora N, Bansal MP, and Koul A Indian J. Biochem. Biophys. 50(2), 105-13, (2013)

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Differentiating asthma phenotypes in young adults through polyclonal cytokine profiles. Zoratti E, Havstad S, Wegienka G, et al. Ann. Allergy Asthma Immunol. 113(1), 25-30, (2014)

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Epigenetic regulation of the metallothionein-1A promoter by PU.1 during differentiation of THP-1 cells. Suzuki S, Nakano H, and Takahashi S Biochem. Biophys. Res. Commun. 433(3), 349-53, (2013)

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Inhibition of message for FcepsilonRI alpha chain blocks mast cell IL-4 production induced by co-culture with Mycoplasma pneumoniae. Luo D Microb. Pathog. 44(4), 286-92, (2008)

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Effects of two disiloxanes ALIS-409 and ALIS-421 on chemoprevention in model experiments. Tokuda H, Maoka T, Suzuiki N, et al. Anticancer Res. 33(5), 2021-7, (2013)

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Homologous desensitization of histamine-mediated signal transduction system in C6 glioma cells. Tseng CL and Wei JW Chin. J. Physiol. 56(2), 90-100, (2013)

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IL-31 is produced by the malignant T-cell population in cutaneous T-Cell lymphoma and correlates with CTCL pruritus. Singer EM, Shin DB, Nattkemper LA, et al. J. Invest. Dermatol. 133(12), 2783-5, (2013)

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