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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:
16561-29-8
Molecular Weight:
616.83
Beilstein/REAXYS Number:
2407201
MDL number:
MFCD00036736
UNSPSC Code:
12352200
PubChem Substance ID:
24898219
NACRES:
NA.52

grade

for molecular biology

Quality Level

200

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

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

wgk_germany

WGK 3

ppe

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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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)
Identification of a potential biomarker for FABP4 inhibition: the power of lipidomics in preclinical drug testing
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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.
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