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Key Documents

P8139

Sigma-Aldrich

Phorbol 12-myristate 13-acetate

≥99% (TLC), film or powder, PKC activator

Synonyma:

12-O-Tetradecanoylphorbol 13-acetate, 4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate, PMA, TPA

Přihlásitk zobrazení cen stanovených pro organizaci a smluvních cen


About This Item

Empirický vzorec (Hillův zápis):
C36H56O8
Číslo CAS:
Molekulová hmotnost:
616.83
Beilstein/REAXYS Number:
2407201
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.77

product name

Phorbol 12-myristate 13-acetate, ≥99% (TLC), film or powder

Quality Level

assay

≥99% (TLC)

form

film or powder

solubility

DMSO: soluble
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

Dissolve in water-miscible organic solvent prior to preparing aqueous solutions. DMSO solutions can be stored dark at -20 °C for at least six months.
Phorbol 12-myristate 13-acetate (PMA) exhibits high inflammatory properties. It stimulates protein kinase C (PKC) activity. PMA induces the release of proteases, cytokines, and NADPH oxidases, leading to tissue damage or histamine production, and promoting vascular remodeling, redness, heat, and tumor promotion. Additionally, it enhances reactive oxygen species (ROS) production and decreases enzymes involved in ROS detoxification. PMA also inhibits the basal level of superoxide dismutase (SOD), catalase, and glutathione peroxidase.
Phorbol 12-myristate 13-acetate is a phorbol ester. It works as a tumor promoter and is involved in gene transcription, cell growth, differentiation, programmed cell death, immune pathway and receptor desensitization via protein kinase C (PKC) signaling pathways. Phorbol 12-myristate 13-acetate is also a model agent to study growth factors-, hormones-, and cytokines-mediated regulation of cellular growth and differentiation.

Application

Phorbol 12-myristate 13-acetate has been used:
  • to induce differentiation of THP-1monocytes to macrophage.
  • to stimulate the proliferation of peripheral blood lymphocytes.
  • to induce respiratory bursts and enhance the generation of ultra-weak photon emission (UPE) from the neutrophil-like cells derived from HL-60 cells.
  • in conjugation with Ionomycin calcium salt to stimulate T-cell activation
  • for the stimulation of various cells including spleen cells, quiescent lymphocytes, and fetal thymocytes.
  • for the activation of PKC (protein kinase C) in cells.

Features and Benefits

This compound is featured on the PKC page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Caution

Photosensitive

related product

Č. produktu
Popis
Stanovení ceny

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


Osvědčení o analýze (COA)

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Navštívit knihovnu dokumentů

Phorbol 12-Myristate 13-Acetate Induced Toxicity Study and the Role of Tangeretin in Abrogating HIF-1 alpha-NF-kappa B Crosstalk In Vitro and In Vivo
Chang SN, et al.
International Journal of Molecular Sciences (2020)
Inhibition of protein kinase C results in decreased expression of bovine leukemia virus.
Jensen WA et al.
Journal of Virology, 66, 4427-4427 (1992)
Phorbol 12-myristate 13-acetate up-regulates the transcription of MUC2 intestinal mucin via Ras, ERK, and NF-kappa B.
Lee HW et al.
The Journal of Biological Chemistry, 277, 32624-32624 (2002)
Rejection of H-Y disparate skin grafts by monospecific CD4+ Th1 and Th2 cells: no requirement for CD8+ T cells or B cells.
Zelenika D, et al.
Journal of Immunology, 161, 1868-1868 (1998)
Liwang Liu et al.
Journal of biophotonics, 12(8), e201900045-e201900045 (2019-05-31)
Advances in microscopy with new visualization possibilities often bring dramatic progress to our understanding of the intriguing cellular machinery. Picosecond optoacoustic micro-spectroscopy is an optical technique based on ultrafast pump-probe generation and detection of hypersound on time durations of picoseconds

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