Ingenol 3,20-dibenzoate

For research use only, not for therapeutic use.

  • CAT Number: I029366
  • CAS Number: 59086-90-7
  • Molecular Formula: C34H36O7
  • Molecular Weight: 556.66
  • Purity: 98%
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Ingenol 3,20-dibenzoate(Cat No.:I029366)is a synthetic derivative of ingenol, a natural product derived from the sap of the Euphorbia genus. This compound exhibits potential anti-inflammatory and anti-cancer properties by modulating immune responses and inducing apoptosis in tumor cells. Ingenol 3,20-dibenzoate has been studied for its effects on skin lesions, particularly in the treatment of actinic keratosis and non-melanoma skin cancers. Its mechanism involves activation of protein kinase C and subsequent pathways that lead to cell death and immune activation. This compound offers a promising avenue for developing topical therapies for skin malignancies.


Catalog Number I029366
CAS Number 59086-90-7
Synonyms

Ingenol 3,20-dibenzoate; Ingenol 3,20 dibenzoate; IDB

Molecular Formula C34H36O7
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name [(1S,4S,5S,6R,9S,10R,12R,14R)-4-benzoyloxy-5,6-dihydroxy-3,11,11,14-tetramethyl-15-oxo-7-tetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dienyl]methyl benzoate
InChI InChI=1S/C34H36O7/c1-19-17-33-20(2)15-25-26(32(25,3)4)24(28(33)36)16-23(18-40-30(37)21-11-7-5-8-12-21)27(35)34(33,39)29(19)41-31(38)22-13-9-6-10-14-22/h5-14,16-17,20,24-27,29,35,39H,15,18H2,1-4H3/t20-,24+,25-,26+,27-,29+,33+,34+/m1/s1
InChIKey GIMKEHNOTHXONN-NXBFFCPZSA-N
SMILES C[C@@H]1C[C@@H]2[C@@H](C2(C)C)[C@@H]3C=C([C@H]([C@]4([C@@]1(C3=O)C=C([C@@H]4OC(=O)C5=CC=CC=C5)C)O)O)COC(=O)C6=CC=CC=C6
Reference

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2: Oh JG, Chin YW, Kim SJ, Choi JM, Kim SK, Kang HE, Heo TH. Biphasic Effects of Ingenol 3,20-Dibenzoate on the Erythropoietin Receptor: Synergism at Low Doses and Antagonism at High Doses. Mol Pharmacol. 2015 Aug;88(2):392-400. doi: 10.1124/mol.114.097436. Epub 2015 Jun 5. PubMed PMID: 26048958.
3: Racke FK, Baird M, Barth RF, Huo T, Yang W, Gupta N, Weldon M, Rutledge H. Unique in vitro and in vivo thrombopoietic activities of ingenol 3,20 dibenzoate, a Ca(++)-independent protein kinase C isoform agonist. PLoS One. 2012;7(12):e51059. doi: 10.1371/journal.pone.0051059. Epub 2012 Dec 21. PubMed PMID: 23284657; PubMed Central PMCID: PMC3528756.
4: Desmond R, Dunfee A, Racke F, Dunbar CE, Larochelle A. CD9 up-regulation on CD34+ cells with ingenol 3,20-dibenzoate does not improve homing in NSG mice. Blood. 2011 May 26;117(21):5774-6. doi: 10.1182/blood-2011-01-332031. PubMed PMID: 21617010; PubMed Central PMCID: PMC3110034.
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10: Wang W, Cui Q, Li Y, Li B, Yang X, Cui L, Jin H, Qu L. The role of ERK-1/2 in the N/OFQ-induced inhibition of delayed rectifier potassium currents. Biochem Biophys Res Commun. 2010 Apr 16;394(4):1058-62. doi: 10.1016/j.bbrc.2010.03.123. Epub 2010 Mar 21. PubMed PMID: 20331962.
11: Poole DP, Matsuyama H, Nguyen TV, Eriksson EM, Fowler CJ, Furness JB. Inflammation and inflammatory agents activate protein kinase C epsilon translocation and excite guinea-pig submucosal neurons. Gastroenterology. 2007 Oct;133(4):1229-39. Epub 2007 Jul 10. PubMed PMID: 17765238.
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14: Blanco-Molina M, Tron GC, Macho A, Lucena C, Calzado MA, Muñoz E, Appendino G. Ingenol esters induce apoptosis in Jurkat cells through an AP-1 and NF-kappaB independent pathway. Chem Biol. 2001 Aug;8(8):767-78. PubMed PMID: 11514226.
15: Weller SG, Klein IK, Penington RC, Karnes WE Jr. Distinct protein kinase C isozymes signal mitogenesis and apoptosis in human colon cancer cells. Gastroenterology. 1999 Oct;117(4):848-57. PubMed PMID: 10500067.

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