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Ingenol 3,20-dibenzoate

BML-PE186

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PKC activator

Ingenol is a diterpenoid related to phorbol. Activates protein kinase C (PKC) and competes with [³H]phorbol dibutyrate for binding to PKCα (K_i 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.

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Product Details

Alternative Name	IDB
Appearance	White solid.
CAS	59086-90-7
Couple Target	PKC
Couple Type	Activator
Formula	C₃₄H₃₆O₇
MW	556.7
Purity	≥97%
Solubility	Soluble in DMSO (20mg/ml) or ethanol (20mg/ml).

Handling & Storage

Use/Stability	As indicated on product label or CoA when stored as recommended. 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.
Long Term Storage	-20°C
Shipping	Ambient Temperature

Regulatory Status	RUO – Research Use Only

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

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Ingenol 3,20-dibenzoate

BML-PE186

Product Details

Handling & Storage

Datasheet, Manuals, SDS & CofA

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