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Merck

P1585

PMA

for use in molecular biology applications, ≥99% (HPLC), Molecular Biology

Synonym(s):

Phorbol 12-myristate 13-acetate, NF-κB Activator, PKC Activator, croton oil, phorbol ester, protein kinase C activator, 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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About This Item

Empirical Formula (Hill Notation):
C36H56O8
CAS Number:
Molecular Weight:
616.83
UNSPSC Code:
12352200
NACRES:
NA.52
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
2407201
Assay:
≥99% (HPLC)
Form:
(Lyophilisate)
Quality level:
Storage condition:
protect from light
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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

SMILES string

CCCCCCCCCCCCCC(=O)O[C@@H]1[C@@H](C)[C@@]2(O)C(C=C(CO)C[C@@]3(O)C2C=C(C)C3=O)C4C(C)(C)[C@]14OC(C)=O

InChI key

PHEDXBVPIONUQT-RGYGYFBISA-N

grade

Molecular Biology

assay

≥99% (HPLC)

form

(Lyophilisate)

mol wt

616.83  g/mol

storage condition

protect from light

solubility

DMSO: soluble (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

Quality Level

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General description

PMA (Phorbol 12-myristate 13-acetate) is an activator of protein kinase C (PKC) and a known tumor promoting agent. PMA also exhibits clastogenic (chromosome-breaking) activity.
Phorbol 12-myristate 13-acetate (PMA) can induce the activity of PLD1 (phospholipase D1) but not PLD2 (phospholipase D2).

Through the protein kinase C (PKC) signaling pathway, PMA is a tumor promoter associated with:

  • gene transcription
  • cell growth
  • cell differentiation
  • programmed cell death
  • immune pathway
  • receptor desensitization

Phorbol 12-myristate 13-acetate is used to study:

  • growth factors
  • hormones
  • cytokines-mediated regulation of cellular growth and differentiation

Application

PMA has been used:
  • for the detection of intracellular cytokines
  • in CellROX oxidative stress assay
  • for Huh7 cell stimulation to investigate dipeptidyl peptidase 9 (DPP9) re-distribution
  • as a positive control in B-cell receptor (BCR) stimulation of chronic lymphocytic leukaemia (CLL) cells
  • in the differentiation of monocytes (THP -1) into macrophages

Suitable for
  • molecular biology studies as standard
  • analytical studies of tumor promoters
  • promotion of cell growth

Biochem/physiol Actions

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

Features and Benefits

  • Stimulation of interleukin 2 production of Jurkat cells
  • T-cell stimulation
  • Protein kinase C (PKC) activator
  • NF-κB Activator
  • Promotion of cell growth
  • Used in analytical studies of tumor promoters
  • Molecular Biology grade

Analysis Note

  • Stimulation of interleukin 2 production of Jurkat cells
  • T-cell stimulation
  • Protein kinase C (PKC) activator
  • NF-κB Activator
  • Promotion of cell growth
  • Used in analytical studies of tumor promoters
  • Molecular Biology grade

Disclaimer

Photosensitive, protect from light.

signalword

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 1 Inhalation - Acute Tox. 2 Oral - Carc. 2 - Eye Dam. 1 - Resp. Sens. 1 - Skin Corr. 1B - Skin Sens. 1

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves


Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

P1585-1MG-PW: + P1585-25MG-PW: + P1585-10MG-PW: + P1585-25MG: + P1585-5MG-PW: + P1585-BULK: + P1585-1MG: + P1585-VAR: + P1585-10MG: + P1585-5MG:

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The immune responses of central and effector memory BCG-specific CD4+ T cells in BCG-vaccinated PPD+ donors were modulated by Treg cells
Li L, et al.
Immunobiology, 216(4), 477-484 (2011)
Identification of a potential biomarker for FABP4 inhibition: the power of lipidomics in preclinical drug testing
Suhre K, et al.
Journal of Biomolecular Screening, 16(5), 467-475 (2011)
Biological properties and measurement of phospholipase D activation by ADP-ribosylation factor (ARF)
Cockcroft S, et al.
Methods in Enzymology, 329, 355-372 (2001)
B Manger et al.
The Journal of clinical investigation, 77(5), 1501-1506 (1986-05-01)
Different T cell lines, which can be induced to secrete interleukin 2 (IL-2) in vitro, were used to dissect the effect of cyclosporin A (CsA). The T leukemia cell Jurkat requires an increase in cytoplasmic calcium concentration ([Ca++]i) and phorbol
Tumour promoter phorbol-12-myristate-13-acetate induces chromosomal damage via indirect action.
I Emerit et al.
Nature, 293(5828), 144-146 (1981-09-10)

Related Content

T-cell activation is normally triggered by the interaction of a cell surface receptor to its specific ligand molecule

PMA, through its activation of PKC, can activate T-cells and stimulate low-level production of IL-2. When Jurkat cells are stimulated by PMA and a co-stimulator, such as PHA, IL-2 production is strongly enhanced2.

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