Stock solutions should be made in pure, anhydrous DMSO.
P8139
Phorbol 12-myristate 13-acetate
≥99% (TLC), film or powder, PKC activator
Phorbol 12-myristate 13-acetate
Synonym(s):
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
MXP 3,134.00
5 MG
MXP 7,496.00
10 MG
MXP 14,904.00
25 MG
MXP 23,610.00
MXP 3,134.00
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About This Item
Empirical Formula (Hill Notation):
C36H56O8
CAS Number:
Molecular Weight:
616.83
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352211
MDL number:
Beilstein/REAXYS Number:
2407201
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Product Name
Phorbol 12-myristate 13-acetate, ≥99% (TLC), film or powder
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
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 key
PHEDXBVPIONUQT-RGYGYFBISA-N
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
Quality Level
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Related Categories
1 of 4
This Item | 79346 | P1585 | P148 |
|---|---|---|---|
| form film or powder | form film | form (Lyophilisate) | form solid |
| assay ≥99% (TLC) | assay ≥98.0% (TLC) | assay ≥99% (HPLC) | assay ≥95% (TLC) |
| Quality Level 200 | Quality Level 200 | Quality Level 200 | Quality Level 100 |
| storage temp. −20°C | storage temp. −20°C | storage temp. −20°C | storage temp. −20°C |
| solubility DMSO: soluble, ethanol: soluble (Dissolve in water-miscible organic solvent prior to preparing aqueous solutions.) | solubility chloroform: 10 mg/mL, clear, colorless to light yellow | 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) | solubility H2O: ~2 μM, DMSO: soluble, ethanol: soluble |
Application
Phorbol 12-myristate 13-acetate has been used:
- to induce differentiation of THP-1monocytes to macrophage.[1]
- to stimulate the proliferation of peripheral blood lymphocytes.[2]
- to induce respiratory bursts and enhance the generation of ultra-weak photon emission (UPE) from the neutrophil-like cells derived from HL-60 cells.[3]
- in conjugation with Ionomycin calcium salt to stimulate T-cell activation[4]
- for the stimulation of various cells including spleen cells, quiescent lymphocytes, and fetal thymocytes.[5][6][7]
- for the activation of PKC (protein kinase C) in cells.[8]
Disclaimer
Photosensitive
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.
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.[9]
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.[10]
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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
WGK 3
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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)
Cytokine requirements for the growth and development of mouse NK cells in vitro.
Toomey JA et al.
Journal of Leukocyte Biology, 74, 233-233 (2003)
Arginine and glutamine supplementation to culture media improves the performance of various channel catfish immune cells
Pohlenz C, et al.
Journal of Separation Science, 32(5), 762-768 (2012)
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)
Articles
Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete.
Related Content
Product Information Sheet
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When making up the 20mM solution of PMA, what percentage/molarity of DMSO should be within this solution? Is the solution in water + DMSO?
1 answer-
Helpful?
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Hello, do you have any information on the stability of this product with regard to freeze/thaw after it is reconstituted? We normally thaw our aliquot, take what we need, and then refreeze our aliquots.
1 answer-
Freeze/thaw cycles are not recommended for this product.
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Why do I not see any solid in the Phorbol 12-myristate 13-acetate bottle, Product P8139?
1 answer-
Phorbol 12-myristate 13-acetate may be an invisible film in the bottle.
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How should I store the solutions of Product P8139, Phorbol 12-myristate 13-acetate?
1 answer-
Stock solutions in DMSO can be stored protected from light as aliquots at -20°C for at least 6 months, or at 2-8°C for up to 3 months.
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What is the difference between Phorbol 12-myristate 13-acetate, Product P8139 and molecular biology grade Product P1585?
1 answer-
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.
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How should Product P8139, Phorbol 12-myristate 13-acetatebe dissolved?
1 answer-
Stock solutions of 20 mM can be prepared in DMSO and diluted into aqueous buffers. View more information on P8139 solubility in the product information sheet (under Documents, above).
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Do you have any application information for Product P8139, Phorbol 12-myristate 13-acetate?
1 answer-
View the P8139 product information sheet (under Documents, above).
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What is the Department of Transportation shipping information for this product?
1 answer-
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.
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