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P1585 Sigma-Aldrich

PMA

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

Synonym: 12-O-Tetradecanoylphorbol 13-acetate, 4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate, NF-κB Activator, PKC Activator, PMA, Phorbol 12-myristate 13-acetate, TPA, croton oil, phorbol ester, protein kinase C activator

  • CAS Number 16561-29-8

  • Empirical Formula (Hill Notation) C36H56O8

  • Molecular Weight 616.83

  •  Beilstein/REAXYS Number 2407201

  •  MDL number MFCD00036736

  •  PubChem Substance ID 24898219

  •  NACRES NA.52

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Properties

Related Categories Biochemicals, Molecular Biology, Molecular Biology Reagents More...
Quality Level   200
grade   for molecular biology
assay   ≥99% (HPLC)
form   film
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

Description

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.

Potent tumor promoter; activates protein kinase C 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

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
QH4377000

Documents

Certificate of Analysis (COA)

Please Enter a Lot Number

Certificate of Origin (COO)

Please Enter a Lot Number

Frequently Asked Questions

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.
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 deg. C for at least six months.
How much Phorbol 12-myristate 13-acetate, Product P1585, product should I use?
A concentration of 50 ng/ml was used on Jurkat cells.
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.
What is the storage temperature for Phorbol 12-myristate 13-acetate, Product P1585?
Phorbol 12-myristate 13-acetate should be stored at -20 deg. C.
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.
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.
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.
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.
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.
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.
My question is not addressed here, how can I contact Technical Service for assistance?
Ask a Scientist here.
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Protocols & Articles

Protocols

Phorbol 12-myristate 13-acetate Molecular Biology Reagent Protocol

T-cell activation is normally triggered by the interaction of a cell surface receptor to its specific ligand molecule. This binding event triggers the rapid hydrolysis of inositol phospholipids to di...
Keywords: Addition reactions, Centrifugation, Enzyme-linked immunosorbent assay, Ligands

Peer-Reviewed Papers
15

References

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