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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

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xi
Risk Statements (Europe) 
38
Safety Statements (Europe) 
36/37
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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Down-regulation of lipoprotein lipase increases ABCA1-mediated cholesterol efflux in THP-1 macrophages. Kawashima RL and Medh JD Biochem. Biophys. Res. Commun. 450(4), 1416-21, (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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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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Intracellular shunting of O2(-) contributes to charge compensation and preservation of neutrophil respiratory burst in the absence of voltage-gated proton channel activity. Decleva E, Menegazzi R, Fasolo A, et al. Exp. Cell Res. 319(12), 1875-88, (2013)

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Resveratrol inhibits K(v)2.2 currents through the estrogen receptor GPR30-mediated PKC pathway. Dong WH, Chen JC, He YL, et al. Am. J. Physiol. Cell Physiol. 305(5), C547-57, (2013)

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Phosphorylation Of VACM-1/Cul5 By Protein Kinase A Regulates Its Neddylation And Antiproliferative Effect. Bradley, S.E., et al. J. Thorac. Cardiovasc. Surg. 285, 4883-95, (2010)

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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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New ex vivo approaches distinguish effective and ineffective single agents for reversing HIV-1 latency in vivo. Bullen CK, Laird GM, Durand CM, et al. Nat. Med. 20(4), 425-9, (2014)

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KCNT1 gain of function in 2 epilepsy phenotypes is reversed by quinidine. Milligan CJ, Li M, Gazina EV, et al. Ann. Neurol. 75(4), 581-90, (2014)

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Impaired wound repair in adult endoglin heterozygous mice associated with lower NO bioavailability. Pérez-Gómez E, Jerkic M, Prieto M, et al. J. Invest. Dermatol. 134(1), 247-55, (2014)

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Nipah virus infects specific subsets of porcine peripheral blood mononuclear cells. Beata Stachowiak et al PLoS ONE 7, e30855, (2012)

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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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Phytosphingosine derivatives ameliorate skin inflammation by inhibiting NF-κB and JAK/STAT signaling in keratinocytes and mice. Kim BH, Lee JM, Jung YG, et al. J. Invest. Dermatol. 134(4), 1023-32, (2014)

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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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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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Preparation of low molecular weight fucoidan by gamma-irradiation and its anticancer activity. Choi JI and Kim HJ Carbohydr. Polym. 97(2), 358-62, (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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Toll-like receptor 2 activation by β2→1-fructans protects barrier function of T84 human intestinal epithelial cells in a chain length-dependent manner. Vogt LM, Meyer D, Pullens G, et al. J. Nutr. 144(7), 1002-8, (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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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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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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Differential cellular uptake and metabolism of curcuminoids in monocytes/macrophages: regulatory effects on lipid accumulation. Nakagawa K, Zingg JM, Kim SH, et al. Br. J. Nutr. 112(1), 8-14, (2014)

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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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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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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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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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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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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 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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Targeted deletion of RasGRP1 impairs skin tumorigenesis. Sharma A, Fonseca LL, Rajani C, et al. Carcinogenesis 35(5), 1084-91, (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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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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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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Characterization of cytosolic proliferating cell nuclear antigen (PCNA) in neutrophils: antiapoptotic role of the monomer. De Chiara A, Pederzoli-Ribeil M, Mocek J, et al. J. Leukoc. Biol. 94(4), 723-31, (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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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Reduced susceptibility to two-stage skin carcinogenesis in mice with epidermis-specific deletion of CD151. Sachs N, Secades P, van Hulst L, et al. J. Invest. Dermatol. 134(1), 221-8, (2014)

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PKM2 inhibitor shikonin suppresses TPA-induced mitochondrial malfunction and proliferation of skin epidermal JB6 cells. Li W, Liu J, and Zhao Y Mol. Carcinog. 53(5), 403-12, (2014)

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