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044954 Ingenol-3-angelate CAS: 75567-37-2

Specifications
References
CAS Number
75567-37-2
Grade
Highly Purified
MDL Number
MFCD22683801
Molecular Formula
C25H34O6
Molecular Weight
430.5
EU Commodity Code
38220090
Shipping Temp
Blue Ice
Storage Temp
4°C/-20°C

Ingenol 3-Angelate is a diterpenoid ester isolated from Euphorbia peplus that induces rapid cell death with keratinocytes and some cancer cell lines. Ingenol 3-Angelate is a protein kinase C activator that displays potent antileukemic activity. Ingenol 3-Angelate (ingenol mebutate) is used for treatment of actinic keratosis.

Source
Semi-synthetic, the starting material ingenol was isolated from Euphorbia latyris.
Synonyms
PEP005; I3A; Ingenol mebutate
CAS Number
75567-37-2
Molecular Weight
430.5
Molecular Formula
C25H34O6
Solubility
100% ethanol, DMSO or dichloromethane.
Appearance
Supplied as a white to off-white solid.
Method for Determining Identity
Proton NMR
Purity
≥97% (HPLC)
Storage and Stability
May be stored at 4°C for short-term only. Stable for 12 months after receipt when stored at -20°C. For maximum recovery of product, centrifuge the original vial prior to removing the cap.
Important Note
This product as supplied is intended for research use only, not for use in human, therapeutic or diagnostic applications without the expressed written authorization of United States Biological.
Toxicity and Hazards
 All products should be handled by qualified personnel only, trained in laboratory procedures.
References
1. Characterization of the interaction of ingenol 3-angelate with protein kinase C: N. Kedei, et al.; Cancer Res. 64, 3243 (2004)|2. 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)|3. 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)|4. 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)|5. 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)|6. Immunostimulatory cancer chemotherapy using local ingenol-3-angelate and synergy with immunotherapies: T.T. Le, et al.; Vaccine 27, 3053 (2009)|7. 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)|8. Novel antileukemic compound ingenol 3-angelate inhibits T cell apoptosis by activating protein kinase Ctheta: W.Y. Lee, et al.; JBC 285, 23889 (2010)
USBio References
No references available
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