| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| Other Sizes |
| Targets |
Ingenol 3,20-dibenzoate is a selective agonist of specific protein kinase C (PKC) isoforms. It effectively induces the translocation of nPKC-delta, -epsilon, and -theta, as well as PKC-mu, from the cytosolic fraction to the particulate fraction. It competes with [³H]phorbol dibutyrate for binding to PKCα with a Ki of 240 nM. By activating these PKC isoforms, it modulates a wide range of cellular processes including cell growth, differentiation, and apoptosis.
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| ln Vitro |
A549 cells and H1299 cells trigger NK cell degranulation, which is enhanced by ingenol 3,20-dibenzoate (0–1000 nM; 4 hours) [2]. With an EC50 of 0.27 μg/mL (485 nM), ingenol 3,20-dibenzoate (0.001-10 μg/mL) dose-signally stimulates UT-7/EPO cell proliferation [3].
In vitro, Ingenol 3,20-dibenzoate induces apoptosis in various cancer cell lines. It also increases IFN-γ production and degranulation by NK cells, particularly when stimulated by NSCLC cells. It acts as a functional corrector of some LQTS2 mutant channels, highlighting its potential in studying cardiac ion channel function. |
| ln Vivo |
Ingenol 3,20-dibenzoate (20 μg/mouse; i.p.; on days 3, 7, and 11) inhibited the cooling of 5-fluorouric route replacement in an in vivo simulation model [3 ].
In vivo, 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 anti-inflammatory effects have also been observed in animal models. As a PKC activator, it can induce biological responses such as the release of neurotransmitters and the modulation of other cellular responses. |
| Enzyme Assay |
PKC binding affinity is determined using a competitive radioligand binding assay. Membrane preparations are incubated with [³H]phorbol dibutyrate and varying concentrations of Ingenol 3,20-dibenzoate. The Ki value is calculated from the competition curve, and for PKCα it is reported at 240 nM.
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| Cell Assay |
Apoptosis induction is assessed in cultured cancer cell lines. Cells are treated with the compound, and apoptosis is measured using assays for caspase-3/7 activation, Annexin V staining, or DNA fragmentation. The EC50 for apoptosis induction is calculated to determine its potency.
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| Animal Protocol |
Animal/Disease Models: Male C57BL/6 mice (8-12 weeks old) [3]
Doses: 20 μg/mouse Route of Administration: intraperitoneal (ip) injection; results on days 3, 7 and 11: IDB treatment alleviated on days 12 and 20 The severity of anemia caused by 5-FU. In vivo efficacy is evaluated in animal models of cancer, such as mice bearing tumor xenografts. Ingenol 3,20-dibenzoate is administered topically or systemically, and tumor growth, histopathology, and immune cell infiltration are assessed. |
| ADME/Pharmacokinetics |
As a diterpenoid ester, Ingenol 3,20-dibenzoate is expected to have moderate oral bioavailability. Its pharmacokinetic properties, including absorption, distribution, metabolism, and excretion, are typical of this class of compounds. It is soluble in DMSO and ethanol at 20 mg/ml.
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| Toxicity/Toxicokinetics |
As a PKC activator, potential toxicities include inflammation, skin irritation at the application site, and systemic effects related to PKC activation, such as modulation of cell growth and differentiation. These effects are dose-dependent and can be managed by careful dosing.
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| References |
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| Additional Infomation |
Ingenol 3,20-dibenzoate is a benzoate.
See also: Ingenol dibenzoate (note moved to). Ingenol 3,20-dibenzoate is a research compound that has been studied for its potential in treating skin cancers and actinic keratosis. It is structurally related to ingenol mebutate, a marketed drug for actinic keratosis. It is also used to study the structure-activity relationships that govern the interactions between PKC isoforms and their ligands. |
| Molecular Formula |
C34H36O7
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|---|---|
| Molecular Weight |
556.66
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| Exact Mass |
556.246
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| CAS # |
59086-90-7
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| PubChem CID |
442043
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| Appearance |
White to off-white solid powder
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| Density |
1.32 g/cm3
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| Boiling Point |
697ºC at 760 mmHg
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| Flash Point |
221.6ºC
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| Index of Refraction |
1.639
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| LogP |
4.544
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
41
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| Complexity |
1160
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| Defined Atom Stereocenter Count |
8
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| 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
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| InChi Key |
GIMKEHNOTHXONN-NXBFFCPZSA-N
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| InChi Code |
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
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| Chemical 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
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| Synonyms |
IDB; Ingenol 3,20 dibenzoate; Ingenol 3,20-dibenzoate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~179.65 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 5 mg/mL (8.98 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 50.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.7964 mL | 8.9821 mL | 17.9643 mL | |
| 5 mM | 0.3593 mL | 1.7964 mL | 3.5929 mL | |
| 10 mM | 0.1796 mL | 0.8982 mL | 1.7964 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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