AdipoGen Life Sciences

Ingenol-3-angelate

CHF 140.00
In stock
AG-CN2-0012-M0011 mgCHF 140.00
AG-CN2-0012-M0055 mgCHF 420.00
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Product Details
Synonyms PEP005; I3A; Ingenol mebutate
Product Type Chemical
Properties
Formula

C25H34O6

MW 430.5
CAS 75567-37-2
Source/Host Chemicals Semi-synthetic.
Purity Chemicals ≥97% (HPLC)
Appearance White to off-white solid.
Solubility Soluble in 100% ethanol, DMSO or dichloromethane.
Identity Determined by 1H-NMR.
Other Product Data

The starting material ingenol was isolated from Euphorbia latyris.

InChi Key VDJHFHXMUKFKET-XCHJBCONSA-N
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
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
Description
  • Specific protein kinase C (PKC) activator [1].
  • Selective activator of PKC isoforms, like PKCθ 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].
Product 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)
  9. Targeting cutaneous T-Cell Lymphoma Cells by Ingenol Mebutate (PEP005) correlates with PKCδ activation, ROS induction as well as Downregulation of XIAP and c-FLIP: U. Sumarni, et al.; Cells 10, 987 (2021)
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