Ingenol-3-angelate
Product Code: AG-CN2-0012
Product Group: Natural Products and Extracts
Supplier: AdipoGen Life Sciences
| Code | Size | Price |
|---|
| AG-CN2-0012-M001 | 1 mg | £105.00 |
Quantity:
| AG-CN2-0012-M005 | 5 mg | £300.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
-20°C
Documents
Further Information
Alternate Names/Synonyms:
PEP005; I3A; Ingenol mebutate
Appearance:
White to off-white solid.
CAS:
75567-37-2
EClass:
32160000
Form (Short):
liquid
InChi:
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
InChiKey:
VDJHFHXMUKFKET-XCHJBCONSA-N
Long Description:
Chemical. CAS: 75567-37-2. Formula: C25H34O6. MW: 430.5. Semi-synthetic. Specific protein kinase C (PKC) activator. Selective activator of PKC isoforms, like PKCtheta in T cells. Antiproliferative and proapoptotic (necrotic). Immunostimulant. Chemotherapeutic. Anticancer compound. Efficacious agent against actinic kerastosis. Antileukemic.
MDL:
MFCD22683801
Molecular Formula:
C25H34O6
Molecular Weight:
430.5
Other data:
The starting material ingenol was isolated from Euphorbia latyris.
Package Type:
Vial
Product Description:
Specific protein kinase C (PKC) activator [1]. Selective activator of PKC isoforms, like PKCtheta in T cells [1, 5, 8]. Antiproliferative and proapoptotic (necrotic) [2, 3, 5]. Immunostimulant [6]. Chemotherapeutic [4, 6]. Anticancer compound [2, 3, 5]. Efficacious agent against actinic keratosis [7]. Antileukemic [8].
Purity:
>97% (HPLC)
SMILES:
[H][C@@]12C(C[C@@H](C)[C@]34C=C(C)[C@H](OC(=O)C(C)=C/C)[C@@]3(O)[C@H](O)C(CO)=C[C@]1([H])C4=O)C2(C)C
Solubility Chemicals:
Soluble in 100% ethanol, DMSO or dichloromethane.
Source / Host:
Semi-synthetic.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
Characterization of the interaction of ingenol 3-angelate with protein kinase C: N. Kedei, et al.; Cancer Res. 64, 3243 (2004) | Ingenol 3-angelate induces dual modes of cell death and differentially regulates tumor necrosis factor-related apoptosis-inducing ligand-induced apoptosis in melanoma cells: S.K. Gillespie, et al.; Mol. Cancer Ther. 3, 1651 (2004) | PEP005, a selective small-molecule activator of protein kinase C, has potent antileukemic activity mediated via the delta isoform of PKC: P. Hampson, et al.; Blood 106, 1362 (2005) | Neutrophils are a key component of the antitumor efficacy of topical chemotherapy with ingenol-3-angelate: J.M. Challacombe, et al.; J. Immunol. 177, 8123 (2006) | The anti-tumor agent, ingenol-3-angelate (PEP005), promotes the recruitment of cytotoxic neutrophils by activation of vascular endothelial cells in a PKC-delta dependent manner: P. Hampson, et al.; Cancer Immunol. Immunother. 57, 1241 (2008) | Immunostimulatory cancer chemotherapy using local ingenol-3-angelate and synergy with immunotherapies: T.T. Le, et al.; Vaccine 27, 3053 (2009) | Randomized, double-blind, double-dummy, vehicle-controlled study of ingenol mebutate gel 0.025% and 0.05% for actinic keratosis: L. Anderson, et al.; J. Am. Acad. Dermatol. 60, 934 (2009) | Novel antileukemic compound ingenol 3-angelate inhibits T cell apoptosis by activating protein kinase Ctheta: W.Y. Lee, et al.; JBC 285, 23889 (2010) | Targeting cutaneous T-Cell Lymphoma Cells by Ingenol Mebutate (PEP005) correlates with PKCdelta activation, ROS induction as well as Downregulation of XIAP and c-FLIP: U. Sumarni, et al.; Cells 10, 987 (2021)