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Ingenol 3,20-dibenzoate

PKC activator
BML-PE186-0001 1 mg 253.00 USD
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Replaces Prod. #: ALX-350-032

Ingenol is a diterpenoid related to phorbol. Activates protein kinase C (PKC) and competes with [3H]phorbol dibutyrate for binding to PKCα (Ki for binding=240 nM). Induces apoptosis. Anticancer agent. Shows potent antileukemic activity in the P388 mouse assay. Displays unusually high mouse ear inflammatory activity, even though the 20-hydroxy group is blocked with a benzoate ester. It appears likely that this high potency is due to metabolic cleavage of the 20-benzoate group, which releases the more potent ingenol 3-benzoate.

Product Details

Alternative Name:IDB
Appearance:White solid.
Solubility:Soluble in DMSO (20mg/ml) or ethanol (20mg/ml).
Shipping:Ambient Temperature
Long Term Storage:-20°C
Use/Stability:Stable for at least 1 year after receipt when stored, as supplied, at -20°C. Stock solutions are stable for up to 3 months at -20°C.
Regulatory Status:RUO - Research Use Only
BML-PE186 structure
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BML-PE186 structure

Product Literature References

The tetraspanin CD9 regulates migration, adhesion, and homing of human cord blood CD34+ hematopoietic stem and progenitor cells: K.T. Leu; Blood 117, 1840 (2011), Abstract;
Dual regulation of the cardiac L-type calcium channel in L6 cells by protein kinase C: B.A. Tafti & B.M. Hantash; Cell Calcium 44, 545 (2008), Abstract;
Ingenol derivatives inhibit proliferation and induce apoptosis in breast cancer cell lines: A. Vigone, et al.; Eur. J. Gynaecol. Oncol. 26, 526 (2005), Abstract;
Ingenol esters induce apoptosis in Jurkat cells through an AP-1 and NF-kappaB independent pathway: M. Blanco-Molina, et al.; Chem. Biol. 8, 767 (2001), Abstract;
Induction of thymocyte apoptosis by Ca2+-independent protein kinase C (nPKC) activation and its regulation by calcineurin activation: A. Asada, et al.; J. Biol. Chem. 273, 28392 (1998), Abstract;
Inside-outside stereoisomerism. VII. Methodology for the Synthesis of 3-Oxygenated Ingenanes. The First Ingenol Analogs with High Affinity for Protein Kinase C: J.D. Winkler, et al.; J. Org. Chem. 60, 1381 (1995),
Antileukemic principles isolated from euphorbiaceae plants: S.M. Kupchan, et al.; Science 191, 571 (1976), Abstract;