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Chemical Structure
Chemical Structure
Chemical Structure

Phorbol 12-myristate 13-acetate [16561-29-8]

Research Use Only
AG-CN2-0010
AdipoGen Life Sciences
Estimated Purity>98%
Product group Chemicals
Molecular Weight616.8
Price on request
Packing Size
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Phorbol 12-myristate 13-acetate [16561-29-8]
  • Delivery Days Customer
    10
  • Certification
    Research Use Only
  • Estimated Purity
    >98%
  • Hazard Information
    Non-hazardous,Warning
  • Molecular Formula
    C36H56O8
  • Molecular Weight
    616.8
  • Scientific 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. - 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).
  • 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
  • Storage Instruction
    2°C to 8°C,-20°C
  • UNSPSC
    12352200

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. Fürstenberger, 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)