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Submit ReviewPEP 005
Description: Protein kinase C activator
Alternative Names: Ingenol 3-angelate,Ingenol Mebutate
Chemical Name: (2Z)-2-Methyl-2-butenoic acid (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-1a,2,5,5a,6,9,10,10a-octahydro-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1H-2,8a-methanocyclopenta[a]cyclopropa[e]cyclodecen-6-yl ester
Purity: ≥97% (HPLC)
Biological Activity for PEP 005
PEP 005 is an activator of protein kinase C (PKC). Exhibits antileukemic activity; induces nuclear translocation of PKCδ, and induces apoptosis in acute myeloid leukemia (AML) cell lines and primary AML blast cells. Also displays antiproliferative effects and induces apoptosis in Colo205 cells. Reactivates latent HIV in cell culture. Also reactivates hypofunctional CD8+ T cells during chronic viral infection. Acts as a substrate for multidrug transporter.
Technical Data for PEP 005
| M. Wt | 430.53 |
| Formula | C25H34O6 |
| Storage | Store at -20°C |
| Purity | ≥97% (HPLC) |
| CAS Number | 75567-37-2 |
| PubChem ID | 6918670 |
| InChI Key | VDJHFHXMUKFKET-WDUFCVPESA-N |
| Smiles | CC([C@@H]2OC(/C(C)=C\C)=O)=C[C@@]1([C@H](C)C4)[C@]2(O)[C@H](O)C(CO)=C[C@]([C@@]3([H])[C@]4([H])C(C)3C)([H])C1=O |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for PEP 005
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 0.86 | 2 |
Preparing Stock Solutions for PEP 005
The following data is based on the product molecular weight 430.53. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 0.02 mM | 116.14 mL | 580.68 mL | 1161.36 mL |
| 0.1 mM | 23.23 mL | 116.14 mL | 232.27 mL |
| 0.2 mM | 11.61 mL | 58.07 mL | 116.14 mL |
| 1 mM | 2.32 mL | 11.61 mL | 23.23 mL |
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Product Datasheets for PEP 005
References for PEP 005
References are publications that support the biological activity of the product.
Benhadji et al (2008) Antiproliferative activity of PEP005, a novel ingenol angelate that modulates PKC functions, alone and in combination with cytotoxic agents in human colon cancer cells. Br.J.Cancer 99 1808 PMID: 19034280
Li et al (2010) The skin cancer chemotherapeutic agent ingenol-3-angelate (PEP005) is a substrate for the epidermal multidrug transporter (ABCB1) and targets tumor vasculature. Cancer Res. 70 4509 PMID: 20460505
Kedei et al (2004) Characterization of the interaction of ingenol-3-angelate with protein kinase C. Cancer Res. 64 3243 PMID: 15126366
Hampson et al (2005) PEP005, a selective small-molecule activator of protein kinase C, has potent antileukemic activity mediated via the delta isoform of PKC. Blood 106 1362 PMID: 15845901
Jiang et al (2015) Synergistic reactivation of latent HIV expression by Ingenol-3-Angelate, PEP005, targeted NF-kB signaling in combination with JQ1 induced p-TEFb activation. PLoS Pathog. 11 e1005066 PMID: 26225771
Marro et al (2019) Discovery of small molecules for the reversal of T cell exhaustion. Cell Rep. 29 3293 PMID: 31801090
If you know of a relevant reference for PEP 005, please let us know.
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Keywords: PEP 005, PEP 005 supplier, Ingenol, 3-angelate, PEP005, protein, kinase, C, PKC, activators, anticancer, antileukemic, PKCd, PKCdelta, PKCδ, T, cells, exhaustion, CD8, hypofunction, ingenol, mebuate, IngMb, Mebutate, Protein, Kinase, Multidrug, Transporters, 4054, Tocris Bioscience
2 Citations for PEP 005
Citations are publications that use Tocris products. Selected citations for PEP 005 include:
Oliver et al (2022) High-content phenotyping of Parkinson's disease patient stem cell-derived midbrain dopaminergic neurons using machine learning classification. Stem Cell Reports 17 2349-2364 PMID: 36179692
Jiang et al (2015) Synergistic reactivation of latent HIV expression by Ingenol-3-Angelate, PEP005, targeted NF-kB signaling in combination with JQ1 induced p-TEFb activation. PloS Pathog. 11 e1005066 PMID: 26225771
Do you know of a great paper that uses PEP 005 from Tocris? Please let us know.
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