CAS Number75567-37-2
Synonyms3-O-angeloylingenol; Ingenol 3-angelate; indican (glucoside); Picato; Ingenol mebutate; Ingenol-3-angelate; 3-Ingenyl angelate; 3-Angeloylingenol
Molecular FormulaC25H34O6
Molecular Weight430.53
Purity≥95 (HPLC)%
Density1.3±0.1 g/cm3
Boiling Point576.9±50.0 °C at 760 mmHg
Appearancepowder
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 75567-37-2 |
| Catalog No. | 2A-9093149 |
| Chinese Name | 丁烯英酯 |
| Synonyms | 3-O-angeloylingenol; Ingenol 3-angelate; indican (glucoside); Picato; Ingenol mebutate; Ingenol-3-angelate; 3-Ingenyl angelate; 3-Angeloylingenol |
| Molecular Formula | C25H34O6 |
| Molecular Weight | 430.53 |
| Purity | ≥95 (HPLC) |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 576.9±50.0 °C at 760 mmHg |
| Appearance | powder |
| Water Solubility | DMSO: soluble15mg/mL, clear | Soluble in 100% etha |
| Storage Condition | ?20°C |
| Application | Ingenol Mebutate is the active ingredient in Euphorbia peplus and is a modulator of PKC. The Ki values for PKC-α, PKC-β, PKC-γ, PKC-δ and PKC-ε are 0.3, 0.105, 0.162, 0.376 and 0.171 nM respectively |
| PubChem ID | 329825782 |
| SMILES | O=C1[C@@]2(C=C(C)[C@@H]3OC(/C(C)=C\C)=O)[C@]3(O)[C@H](O)C(CO)=C[C@@]1([H])[C@@](C4(C)C)([H])[C@@]4([H])C[C@H]2C |
| InChI | 1S/C25H34O6/c1-7-12(2)22(29)31-21-13(3)10-24-14(4)8-17-18(23(17,5)6)16(20(24)28)9-15(11-26)19(27)25(21,24)30/h7,9-10,14,16-19,21,26-27,30H,8,11H2,1-6H3/b12-7-/t14-,16+,17-,18+,19-,21+,24+,25+/m1/s1 |
| InChI Key | VDJHFHXMUKFKET-WDUFCVPESA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | transportation |
| MSDS | msds/93149_1_75567_37_2.pdf |
| Bioactivity | Ingenol Mebutate is an active ingredient in Euphorbia peplus, acts as a potent PKC modulator, with Kis of 0.3, 0.105, 0.162, 0.376, and 0.171 nM for PKC-α, PKC-β, PKC-γ, PKC-δ, and PKC-ε, respectively, and has antiinflammatory and antitumor activity. Related Catalog Signaling Pathways >> Epigenetics >> PKC Signaling Pathways >> TGF-beta/Smad >> PKC Natural Products >> Terpenoids and Glycosides Research Areas >> Cancer Research Areas >> Inflammation/Immunology Target PKC-β:0.105 nM (Ki) PKC-γ:0.162 nM (Ki) PKC-ε:0.171 nM (Ki) PKC-α:0.3 nM (Ki) PKC-δ:0.376 nM (Ki) In Vitro Ingenol Mebutate (Ingenol 3-angelate) is an active ingredient in Euphorbia peplus, acting as a potent PKC activator, with Kis of 0.3, 0.105, 0.162, 0.376, and 0.171 nM for PKC-α, PKC-β, PKC-γ, PKC-δ, and PKC-ε, respectively. Ingenol Mebutate also EC50s of 13 ± 2.4 nM (PKC-α), 4.37 ± 0.4 nM (PKC-βI), 10.5 ± 2.2 nM (PKC-βII), 38.6 ± 2.9 nM (PKC-δ), 1.08 ± 0.01 nM (PKC-ε), 0.9 ± 0.13 nM (PKC-μ) in WEHI-231 cells, 198 ± 12.5 nM (PKC-α), 69.1 ± 8.2 nM (PKC-βI), 4.6 ± 0.4 nM (PKC-ε) and 1 nM (PKC-μ) in HOP-92 cells, 635 ± 245 nM (PKC-α), 146 ± 35 nM (PKC-βI), 4.7 ± 0.7 nM (PKC-δ), 1.1 ± 0.5 nM (PKC-ε), and 30 nM (PKC-μ) in Colo-205 cells. Ingenol Mebutate sensitizes WEHI-231 cells, HOP-92 and Colo-205 cells, with IC50s of 1.41 ± 0.255 nM, 3.24 ± 2.01 nM, and 11.9 ± 1.307 nM, respectively[1]. Ingenol Mebutate (PEP005; 20 nM) actions are PKC-δ dependent, induces apoptosis in primary AML marrow blasts but not in normal myeloblasts[2]. Ingenol Mebutate (PEP005) activates PKCδ and inhibits PKCα. Colo205-R cells (IC50: >10 μM) are >300-fold more resistant to Ingenol Mebutate than parental Colo205-S cells[3]. Cell Assay KG1a cells are transiently transfected with EGFP-tagged mouse PKC-δ subcloned into pEGFP-N1 plasmid using an Amaxa nucleofection apparatus. Cells are treated with Ingenol Mebutate (0.2 μM-20 μM) 24 hours after transfection. Cell viability in EGFP-positive cells is assessed and loss of viability confirmed in the total cell culture by MTT assay after 3 days. Briefly, 24 hours after transfection, 2 × 104 cells are plated in 5 wells in 96-well plates and exposed to 0, 0.2, 2, and 20 μM Ingenol Mebutate. At 72 hours, 20 μL MTT substrate at 5 mg/mL is added and plates are incubated at 37°C. After 3 hours, 150 μL media is removed and replaced with 200 μL dimethyl sulfoxide (DMSO). Absorbance at an optical density (OD) of 550 nm is read on a plate reader and corrected for absorbance obtained from blank media controls[2]. References [1]. Kedei N, et al. Characterization of the interaction of ingenol 3-angelate with protein kinase C. Cancer Res. 2004 May 1;64(9):3243-55. [2]. Hampson P, et al. PEP005, a selective small-molecule activator of protein kinase C, has potent antileukemic activity mediated via the delta isoform of PKC. Blood. 2005 Aug 15;106(4):1362-8. [3]. Ghoul A, et al. Epithelial-to-mesenchymal transition and resistance to ingenol 3-angelate, a novel protein kinase C modulator, in colon cancer cells. Cancer Res. 2009 May 15;69(10):4260-9. Chemical & Physical Properties Density 1.3±0.1 g/cm3 Boiling Point 576.9±50.0 °C at 760 mmHg Molecular Formula C25H34O6 Molecular Weight 430.534 Flash Point 191.4±23.6 °C Exact Mass 430.235535 PSA 104.06000 LogP 5.18 Appearance of Characters white to beige Vapour Pressure 0.0±3.6 mmHg at 25°C Index of Refraction 1.594 InChIKey VDJHFHXMUKFKET-UHFFFAOYSA-N SMILES CC=C(C)C(=O)OC1C(C)=CC23C(=O)C(C=C(CO)C(O)C12O)C1C(CC3C)C1(C)C Storage condition ?20°C Water Solubility DMSO: soluble15mg/mL, clear | Soluble in 100% ethanol, DMSO, dichloromethane, and methanol. Insoluble in water. |
| Use of | Ingenol Mebutate is an active ingredient in Euphorbia peplus, acts as a potent PKC modulator, with Kis of 0.3, 0.105, 0.162, 0.376, and 0.171 nM for PKC-α, PKC-β, PKC-γ, PKC-δ, and PKC-ε, respectively, and has antiinflammatory and antitumor activity. Properties Name ingenol mebutate Synonym More Synonyms Ingenol 3-mebutate Biological Activity Description Ingenol Mebutate is an active ingredient in Euphorbia peplus, acts as a potent PKC modulator, with Kis of 0.3, 0.105, 0.162, 0.376, and 0.171 nM for PKC-α, PKC-β, PKC-γ, PKC-δ, and PKC-ε, respectively, and has antiinflammatory and antitumor activity. Related Catalog Signaling Pathways >> Epigenetics >> PKC Signaling Pathways >> TGF-beta/Smad >> PKC Natural Products >> Terpenoids and Glycosides Research Areas >> Cancer Research Areas >> Inflammation/Immunology PKC-β:0.105 nM (Ki) PKC-γ:0.162 nM (Ki) PKC-ε:0.171 nM (Ki) PKC-α:0.3 nM (Ki) PKC-δ:0.376 nM (Ki) References [1]. Kedei N, et al. Characterization of the interaction of ingenol 3-angelate with protein kinase C. Cancer Res. 2004 May 1;64(9):3243-55. [2]. Hampson P, et al. PEP005, a selective small-molecule activator of protein kinase C, has potent antileukemic activity mediated via the delta isoform of PKC. Blood. 2005 Aug 15;106(4):1362-8. [3]. Ghoul A, et al. Epithelial-to-mesenchymal transition and resistance to ingenol 3-angelate, a novel protein kinase C modulator, in colon cancer cells. Cancer Res. 2009 May 15;69(10):4260-9. Chemical & Physical Properties Molecular Formula C25H34O6 Exact Mass 430.235535 PSA 104.06000 Appearance of Characters white to beige Index of Refraction 1.594 InChIKey VDJHFHXMUKFKET-UHFFFAOYSA-N |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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