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P1585

Sigma-Aldrich

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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1 MG
$156.00
5 MG
$319.00
10 MG
$921.00
25 MG
$1,210.00

$156.00


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About This Item

Empirical Formula (Hill Notation):
C36H56O8
CAS Number:
Molecular Weight:
616.83
Beilstein/REAXYS Number:
2407201
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.52

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grade

Molecular Biology

Quality Level

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

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

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

InChI key

PHEDXBVPIONUQT-RGYGYFBISA-N

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This Item
P8139524400524390
assay

≥99% (HPLC)

assay

≥99% (TLC)

assay

≥98% (HPLC)

assay

≥99% (HPLC)

form

(Lyophilisate)

form

film or powder

form

solid

form

solid (crystalline)

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

mol wt

616.83  g/mol

mol wt

-

mol wt

-

mol wt

-

storage condition

protect from light

storage condition

-

storage condition

OK to freeze

storage condition

OK to freeze

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.[1]
Phorbol 12-myristate 13-acetate (PMA) can induce the activity of PLD1 (phospholipase D1) but not PLD2 (phospholipase D2).[2]

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[3]
  • in CellROX oxidative stress assay[4]
  • for Huh7 cell stimulation to investigate dipeptidyl peptidase 9 (DPP9) re-distribution[5]
  • as a positive control in B-cell receptor (BCR) stimulation of chronic lymphocytic leukaemia (CLL) cells[6]
  • in the differentiation of monocytes (THP -1) into macrophages[7]

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_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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)
Proteomic analysis of B-cell receptor signaling in chronic lymphocytic leukaemia reveals a possible role for kininogen
Kashuba E, et al.
Journal of Proteomics, 91(2), 478-485 (2013)
Biological properties and measurement of phospholipase D activation by ADP-ribosylation factor (ARF)
Cockcroft S, et al.
Methods in Enzymology, 329, 355-372 (2001)
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)
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)

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.

Questions

1–10 of 11 Questions  
  1. I received the product of PMA cat# P1585 in solution. But what is the product of PMA cat#1585 concentration? or volume? without concentration or volume can't be calculate the further dilution.

    1 answer
    1. The stock concentration is 100ug/mL.

      Helpful?

  2. How can I resuspend properly the PMA into the shipped vial? Can I open the vial?

    1 answer
    1. The packaging consists of an amber serum vial sealed with a septum and an aluminum crimp cap. The product is typically dissolved in the vial by injecting the appropriate volume of the selected solvent through the septum using a syringe. Additional solubility and solution stability information can be reviewed in the datasheet available for the general use product, P8139. See the link below to review these recommendations:
      https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/816/596/p8139pis.pdf

      Helpful?

  3. What is the stock concentration of the PMA when adding DMSO. and How much of DMSO do we add?

    1 answer
    1. Suitability Assay - 2.5 ml of Jurkat cells (1 x 10e6 cells/mL) and 2.5 mLof fresh media (RPMI 1640 + 10% fetal calf serum containing 10 ml/l penicillin-streptomycin) were added to 25 cm2 culture bottles.
      The following additions were made in duplicate.
      a. Control - no additions
      b. 1 µg/ml PHA Control - add 10 µl PHA stock solution (0.5 mg/ml PHA in filter-sterilized PBS)
      c. 1 µg/ml PHA + 50 ng/ml PMA – 10 µl PHA stock solution + 2.5 µl PMA stock solution (100 µg/ml PMA in DMSO).

      As stated in part c. - the PMA stock solution is 100µg/ml PMA in DMSO.

      Please see the datasheet for more details:
      https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/311/794/p1585dat.pdf

      Helpful?

  4. What is the stability of stock solutions of Phorbol 12-myristate 13-acetate, Product P1585, and how should I store them?

    1 answer
    1. Stock solutions in DMSO can be stored in the dark as aliquots at -20°C for at least six months.

      Helpful?

  5. How is Product P1585, Phorbol-12-myristate-13-acetate, packaged?

    1 answer
    1. P1585-1MG, P1585-10MG and P1585-25MG come to us pre-packaged by our supplier; all three sizes are packaged the same way. The packaging consists of an amber serum vial with a septum and an aluminum crimp cap. The septum has a PTFE (Teflon) liner, so the material inside the vial could only come in contact with glass and Teflon.

      Helpful?

  6. There isn't any powder in the Phorbol 12-myristate 13-acetate, Product P1585, vial?

    1 answer
    1. The product is usually a clear film on the walls of the vial and may not be easily visible.

      Helpful?

  7. What is the Department of Transportation shipping information for this product?

    1 answer
    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

      Helpful?

  8. What is the difference between Phorbol 12-myristate 13-acetate, Product P8139 and molecular biology grade Product P1585?

    1 answer
    1. Product P1585 has been tested and found suitable for stimulation of interleukin 2 production of Jurkat cells. Product P8139 has not tested in this application.

      Helpful?

  9. How much Phorbol 12-myristate 13-acetate, Product P1585, product should I use?

    1 answer
    1. A concentration of 50 ng/ml was used on Jurkat cells.

      Helpful?

  10. How can I dissolve Phorbol 12-myristate 13-acetate, Product P1585?

    1 answer
    1. Phorbol 12-myristate 13-acetate (PMA) is soluble in DMSO at a 20 mM concentration.  It is also soluble in ethanol.

      Helpful?

1–10 of 11 Questions  

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