Phorbol 12-myristate 13-acetate

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AdipoGen Life Sciences
Product Code: AG-CN2-0010
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AG-CN2-0010-M0011 mg£45.00
Quantity:
AG-CN2-0010-M0055 mg£115.00
Quantity:
AG-CN2-0010-M01010 mg£180.00
Quantity:
AG-CN2-0010-M02525 mg£350.00
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Overview

Regulatory Status: RUO
Shipping:
Ambient
Storage:
-20°C

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Chemical Structure
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Chemical Structure

Documents

Further Information

Alternate Names/Synonyms:
PMA; TPA; 12-O-Tetradecanoylphorbol 13-acetate
Appearance:
White to off-white solid.
CAS:
16561-29-8
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS07
Handling Advice:
Protect from light.
Hazards:
H312, H315
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
InChiKey:
PHEDXBVPIONUQT-RGYGYFBISA-N
Long Description:
Chemical. CAS: 16561-29-8. Formula: C36H56O8. MW: 616.8. Semisynthetic. Most commonly-used phorbol ester. Binds to and activates protein kinase C (PKC) at nM concentrations. Induces cell growth arrest through a variety of pathways including the mitogen-activated protein kinases (MAPKs), p38 and c-Jun N-terminal kinase (JNK) pathways mediated by cyclin dependent kinase (CDK) inhibitors such as p21WAF1/CIP1, p27KIP1, p15 and p16. Potent mouse skin tumor promoter. Promoter of inducible NOS (iNOS; NOS II). Apoptosis inducer. Potential effective cancer therapeutic agent. Inhibitor of anti-lipolytic activity of insulin.
MDL:
MFCD00036736
Molecular Formula:
C36H56O8
Molecular Weight:
616.8
Other data:
Stock solutions are stable for up to 3 months at -20°C.
Package Type:
Vial
Precautions:
P270, P280, P312
Product Description:
PMA/TPA is the most commonly-used phorbol ester [1,2]. Binds to and activates protein kinase C (PKC) at nM concentrations [1,2,9]. Induces cell growth arrest through a variety of pathways including the mitogen-activated protein kinases (MAPKs), p38 and c-Jun N-terminal kinase (JNK) pathways mediated by cyclin dependent kinase (CDK) inhibitors such as p21WAF1/CIP1, p27KIP1, p15 and p16. Potent mouse skin tumor promoter [3,4]. Promoter of inducible NOS (iNOS; NOS II) [5]. Apoptosis inducer [6]. Potential effective cancer therapeutic agent [7,8]. Inhibitor of anti-lipolytic activity of insulin [10]. PMA treatment stimulates THP-1 cells and generates M0 macrophages (M0).
Purity:
>98% (HPLC)
Signal word:
Warning
SMILES:
[H][C@]12[C@]3([H])C=C(CO)C[C@]4(O)C(=O)C(C)=C[C@@]4([H])[C@@]3(O)[C@H](C)[C@@H](OC(=O)CCCCCCCCCCCCC)[C@@]1(OC(C)=O)C2(C)C
Solubility Chemicals:
Soluble in DMSO (20mg/ml), 100% ethanol (20mg/ml), methanol, acetone, ether or dimethylformamide; almost insoluble in aqueous buffers.
Source / Host:
Semisynthetic.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.

References

In vitro studies on the mode of action of the phorbol esters, potent tumor promoters: part 1: P.M. Blumberg; Crit. Rev. Toxicol. 8, 153 (1980) | In vitro studies on the mode of action of the phorbol esters, potent tumor promoters: part 2: P.M. Blumberg; Crit. Rev. Toxicol. 8, 199 (1981) | Skin tumor promotion by phorbol esters is a two-stage process: G. F?rstenberger, et al.; PNAS 78, 7722 (1981) | Phorbol esters as signal transducers and tumor promoters: M. Castagna; Biol. Cell 59, 3 (1987), Review | Phorbol esters induce nitric oxide synthase activity in rat hepatocytes. Antagonism with the induction elicited by lipopolysaccharide: S. Hortelano, et al.; J. Biol. Chem. 267, 24937 (1992) | Phorbol ester induces apoptosis in HL-60 promyelocytic leukemia cells but not in HL-60 PET mutant: D.E. Macfarlane & P.S. O'Donnel; Leukemia 7, 1846 (1993) | Effect of intravenous infusions of 12-O-tetradecanoylphorbol-13- acetate (TPA) in patients with myelocytic leukemia: Preliminary studies on therapeutic efficacy and toxicity: T.H. Zheng, et al.; PNAS 95, 5357 (1998) | 12-O-Tetradecanoylphorbol-13-acetate (TPA)-induced increase in depressed white blood cell counts in patients treated with cytotoxic cancer chemotherapeutic drugs: T.H. Zheng, et al.; PNAS 95, 5362 (1998) | Characterization of phorbol esters activity on individual mammalian protein kinase C isoforms, using the yeast phenotypic assay: L. Saraiva, et al.; Eur. J. Pharmacol. 491, 101 (2004) | Phorbol 12-myristate 13-acetate inhibits the antilipolytic action of insulin, probably via the activity of protein kinase Cepsilon: J. Nakamura; Eur. J. Pharmacol. 648, 188 (2010) | Characterization of polarized THP-1 macrophages and polarizing ability of LPS and food compounds: W. Chanput, et al.; Food Funct. 4, 266 (2013) | M1 and M2 macrophages derived from THP-1 cells differentially modulate the response of cancer cells to etoposide: M. Genin, et al.; BMC Cancer 15, 577 (2015) | Vitamin D3 inhibits the proliferation of T helper cells, downregulate CD4+ T cell cytokines and upregulate inhibitory markers: V. Sheikh, et al. Human Immunol. 79, 439 (2018) | Adults from Kisumu, Kenya have robust gammadelta T cell responses to Schistosoma mansoni, which are modulated by tuberculosis: T.A. McLaughlin, et al.; PLoS Negl. Trop. Dis. 14, e0008764 (2020) | Paeoniflorin reduces the inflammatory response of THP-1 cells by up?regulating microRNA-124: D. Huang, et al.; Genes & Genomics 43, 623 (2021) | Lymphatic dysfunction exacerbates cutaneous tumorigenesis and psoriasis-like skin inflammation through accumulation of inflammatory cytokines: H. Boki, et al.; J. Invest. Dermatol. ahead of print (2021)

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