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P1585

Sigma-Aldrich

PMA

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

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
Beilstein:
2407201
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.52

grade

for 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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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

Caution

Photosensitive, protect from light.

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

Signal Word

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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

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

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

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

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

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

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

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

  5. What is the storage temperature for Phorbol 12-myristate 13-acetate, Product P1585?

    Phorbol 12-myristate 13-acetate should be stored at -20°C.

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

    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.

  7. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  8. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  9. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

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

    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. 

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

    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.

  12. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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)
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)
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

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