Ingenol 3,20-dibenzoateAn activator of protein kinase C (PKC) and apoptotic inducer

Ingenol 3,20-dibenzoate (CAS 59086-90-7)

Ingenol 3,20-dibenzoate | CAS 59086-90-7 is rated 5.0 out of 5 by 1.
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Synonym: IDB
Application: An activator of protein kinase C (PKC) and apoptotic inducer
CAS Number: 59086-90-7
Purity: ≥97%
Molecular Weight: 556.65
Molecular Formula: C34H36O7
* Refer to Certificate of Analysis for lot specific data (including water content).
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Ingenol 3,20-dibenzoate activates PKC (Protein Kinase C) . Induces apoptosis. Anticancer agent. Ingenol 3,20-dibenzoate 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. Ingenol 3,20-dibenzoate is an activator of PKC ε.


References

Antileukemic principles isolated from euphorbiaceae plants: S.M. Kupchan, et al.; Science 191, 571 (1976) Zur Chemie des Ingcnols, II. Ester des Ingenols. und des A'-'-Isoingenols: B. Sorg & E. Hecker; Z. Naturforsch. 37b, 748 (1982) 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) Ingenol esters induce apoptosis in Jurkat cells through an AP-1 and NF-kappaB independent pathway: M. Blanco-Molina, et al.; Chem. Biol. Interact. 8, 767 (2001)

Physical State :
Low-Melting Solid
Solubility :
Soluble in water (partly), DMSO (20 mg/ml), and ethanol (20 mg/ml).
Storage :
Store at -20° C
Melting Point :
20-23° C
Boiling Point :
~697.0° C at 760 mmHg (Predicted)
Density :
~1.3 g/cm3 (Predicted)
Refractive Index :
n20D 1.64 (Predicted)
Ki Data :
Binding to PKCα: Ki= 240 nM
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
319303
MDL Number :
MFCD00211027
SMILES :
C[C@@H]1C[C@@H]2[C@@H](C2(C)C)C3C=C([C@H]([C@]4(C1(C3=O)C=C([C@@H]4OC(=O)C5=CC=CC=C5)C)O)O)COC(=O)C6=CC=CC=C6

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Certificate of Analysis

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Ingenol 3,20-dibenzoate  Product Citations

See how others have used Ingenol 3,20-dibenzoate. Click on the entry to view the PubMed entry .

Citations 1 to 6 of 6 total

PMID: # 30706338  Silva, VAO.|Rosa, MN.|Martinho, O.|Tanuri, A.|Lima, JP.|Pianowski, LF.|Reis, RM.| et al. 2019. Invest New Drugs.

PMID: # 28494238  Boehm, D.|Jeng, M.|Camus, G.|Gramatica, A.|Schwarzer, R.|Johnson, JR.|Hull, PA.|Montano, M.|Sakane, N.|Pagans, S.|Godin, R.|Deeks, SG.|Krogan, NJ.|Greene, WC.|Ott, M.| et al. 2017. Cell Host Microbe. 21: 569-579.e6.

PMID: # 28092804  Gong, C. et al. 2017. Mol. Immunol. 83: 23-32.

PMID: # 27708642  Garrido, C. et al. 2016. Front Immunol. 7: 356.

PMID: # 26151856  Nothias-Scaglia, LF. et al. 2015. Fitoterapia. 105: 202-9.

PMID: # 26171776  Martins, LJ. et al. 2015. AIDS Res. Hum. Retroviruses.

Citations 1 to 6 of 6 total
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Rated 5 out of 5 by from Oh JG;et al Oh JG;et al. (PubMed ID: 26048958) determined Ingenol 3,20-dibenzoate's (known as a selective novel protein kinase C (PKC) agonist) mechanism of action by demonstrating its direct binding to PKCs, thus could be used as a promising new small molecule modulator of EPO-related pathologic conditions. -SCBT Publication Review
Date published: 2015-01-10
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