Art. -Nr.: HY-B0719

Ingenol Mebutate

(Synonyms: Ingenol 3-angelate; PEP005)

5 Cited Publications

Kundenbewertung

Based on 5 publication(s) in Google Scholar

Ingenol Mebutate is an active ingredient in Euphorbia peplus, acts as a potent PKC modulator, with K_is of 0.3, 0.105, 0.162, 0.376, and 0.171 nM for PKC-α, PKC-β, PKC-γ, PKC-δ, and PKC-ε, respectively, and has antiinflammatory and antitumor activity.

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Reinheit: 99.65%
CAS. Nr.: 75567-37-2
Formel: C₂₅H₃₄O₆
Molecular Weight:430.53

Speicherung:

Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 2 years , -20°C, 1 year

Ingenol Mebutate Chemical Structure

CAS. Nr.: 75567-37-2

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Use of MCE Products

Fluorescent Dye

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biologische Aktivität
- Beschreibung
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- Clinical Trial
Chemical Information
Publications (5)
Lösungsmittel & Löslichkeit
- In Vitro
- In Vivo
Protokoll
Reinheit & Dokumentation
Verweise
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

IC₅₀ & Target^[1]

PKC-β

0.105 nM (Ki)

PKC-γ

0.162 nM (Ki)

PKC-ε

0.171 nM (Ki)

PKC-α

0.3 nM (Ki)

PKC-δ

0.376 nM (Ki)

Alle PKC Isoform-spezifische Produkte anzeigen :

Cellular Effect

Cell Line	Type	Value	Description	References
A549	IC₅₀	>50 μM Compound: Ingenol mebutate	Antiproliferative activity against human A549 cells assessed as inhibition of cell growth incubated for 24 to 72 hrs by CCK8 assay Antiproliferative activity against human A549 cells assessed as inhibition of cell growth incubated for 24 to 72 hrs by CCK8 assay	[PMID: 38552425]
HepG2	IC₅₀	>50 μM Compound: Ingenol mebutate	Antiproliferative activity against human HepG2 cells assessed as inhibition of cell growth incubated for 24 to 72 hrs by CCK8 assay Antiproliferative activity against human HepG2 cells assessed as inhibition of cell growth incubated for 24 to 72 hrs by CCK8 assay	[PMID: 38552425]
Keratinocyte	EC₅₀	10.3 nM Compound: 1, PEP005, Ingenol mebutate	Induction of IL-8 release in human primary epidermal keratinocytes after 6 hrs by HTRF assay Induction of IL-8 release in human primary epidermal keratinocytes after 6 hrs by HTRF assay	[PMID: 23993332]
Keratinocyte	EC₅₀	10.3 nM Compound: 1, PEP005, Picato, ingenol mebutate	Induction of proimflammatory activity in human primary epidermal keratinocytes assessed as IL-8 release after 6 hrs Induction of proimflammatory activity in human primary epidermal keratinocytes assessed as IL-8 release after 6 hrs	[PMID: 24332494]
Keratinocyte	EC₅₀	11.2 nM Compound: 1, PEP005, Ingenol mebutate	Induction of TNFalpha release in human primary epidermal keratinocytes after 6 hrs Induction of TNFalpha release in human primary epidermal keratinocytes after 6 hrs	[PMID: 23993332]
Keratinocyte	EC₅₀	11.2 nM Compound: 1, PEP005, Picato, ingenol mebutate	Induction of proimflammatory activity in human primary epidermal keratinocytes assessed as TNFalpha release after 6 hrs Induction of proimflammatory activity in human primary epidermal keratinocytes assessed as TNFalpha release after 6 hrs	[PMID: 24332494]
MT4	CC₅₀	>9.3 μM Compound: 22	Cytotoxicity against human MT4 cells after 3 days by CytoTox-Glo assay Cytotoxicity against human MT4 cells after 3 days by CytoTox-Glo assay	[PMID: 30031972]
MT4	EC₅₀	17 nM Compound: 27	Antiviral activity against HIV1 3B infected in MT4 cells assessed as cell viability after 5 days by MTT assay Antiviral activity against HIV1 3B infected in MT4 cells assessed as cell viability after 5 days by MTT assay	[PMID: 25970561]
MT4	EC₅₀	9 nM Compound: 27	Antiviral activity against HIV2 ROD infected in MT4 cells assessed as cell viability after 5 days by MTT assay Antiviral activity against HIV2 ROD infected in MT4 cells assessed as cell viability after 5 days by MTT assay	[PMID: 25970561]
NCI-H460	IC₅₀	>50 μM Compound: Ingenol mebutate	Antiproliferative activity against human NCI-H460 cells assessed as inhibition of cell growth incubated for 24 to 72 hrs by CCK8 assay Antiproliferative activity against human NCI-H460 cells assessed as inhibition of cell growth incubated for 24 to 72 hrs by CCK8 assay	[PMID: 38552425]
U-937	CC₅₀	>200 nM Compound: Ingenol 3A	Cytotoxicity against human U937 cells assessed as reduction in cell viability after 48 hrs by CellTiter-Glo luminescent cell viability assay Cytotoxicity against human U937 cells assessed as reduction in cell viability after 48 hrs by CellTiter-Glo luminescent cell viability assay	[PMID: 29541372]
Vero	EC₅₀	22.9 μM Compound: 27	Antiviral activity against chikungunya virus Indian ocean strain 899 infected in Vero cells assessed as virus-induced cytopathic effect after 6 to 7 days Antiviral activity against chikungunya virus Indian ocean strain 899 infected in Vero cells assessed as virus-induced cytopathic effect after 6 to 7 days	[PMID: 25970561]

In Vitro

Ingenol Mebutate (Ingenol 3-angelate) is an active ingredient in Euphorbia peplus, acting as a potent PKC activator, with K_is of 0.3, 0.105, 0.162, 0.376, and 0.171 nM for PKC-α, PKC-β, PKC-γ, PKC-δ, and PKC-ε, respectively. Ingenol Mebutate also EC₅₀s of 13 ± 2.4 nM (PKC-α), 4.37 ± 0.4 nM (PKC-βI), 10.5 ± 2.2 nM (PKC-βII), 38.6 ± 2.9 nM (PKC-δ), 1.08 ± 0.01 nM (PKC-ε), 0.9 ± 0.13 nM (PKC-μ) in WEHI-231 cells, 198 ± 12.5 nM (PKC-α), 69.1 ± 8.2 nM (PKC-βI), 4.6 ± 0.4 nM (PKC-ε) and 1 nM (PKC-μ) in HOP-92 cells, 635 ± 245 nM (PKC-α), 146 ± 35 nM (PKC-βI), 4.7 ± 0.7 nM (PKC-δ), 1.1 ± 0.5 nM (PKC-ε), and 30 nM (PKC-μ) in Colo-205 cells. Ingenol Mebutate sensitizes WEHI-231 cells, HOP-92 and Colo-205 cells, with IC₅₀s of 1.41 ± 0.255 nM, 3.24 ± 2.01 nM, and 11.9 ± 1.307 nM, respectively^[1]. Ingenol Mebutate (PEP005; 20 nM) actions are PKC-δ dependent, induces apoptosis in primary AML marrow blasts but not in normal myeloblasts^[2]. Ingenol Mebutate (PEP005) activates PKCδ and inhibits PKCα. Colo205-R cells (IC₅₀: >10 μM) are >300-fold more resistant to Ingenol Mebutate than parental Colo205-S cells^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Clinical Trial

NCT Number	Sponsor	Condition	Start Date	Phase A549
NCT01329991	Plexxikon\|		2011-05	PHASE1

Chemical Information

CAS. Nr. 75567-37-2
Appearance Solid
Molecular Weight 430.53
Formel C₂₅H₃₄O₆
Color White to off-white
SMILES

C/C=C(C)\C(O[C@H]1C(C)=C[C@]23[C@]1(O)[C@H](O)C(CO)=C[C@@](C3=O)([H])[C@@]4([H])[C@@](C4(C)C)([H])C[C@H]2C)=O
Synonyms

Ingenol 3-angelate; PEP005
Structure Classification
- Terpenoids
- Diterpenoids
Initial Source
Versand

Room temperature in continental US; may vary elsewhere.

Speicherung

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	2 years
	-20°C	1 year

Publications (5)

All WBIn Vivo Efficacy StudyIHC

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Journal Impact Factor

Cell Rep Med

DDX5 super-enhancer promotes vasculogenic mimicry formation and metastasis in nasopharyngeal carcinoma by enhancing ADAM10 transcription. [Abstract]

2025 Jun 17;6(6):102146. PMID: 40412383

Ingenol Mebutate purchased from MedChemExpress. Usage Cited in: Cell Rep Med. 2025 Jun 17;6(6):102146. [Abstract]

Western blot analysis of DDX5, ADAM10, and EMT-related markers in CNE2 cells treated with metastasis-exo or Ingenol Mebutate (IM) alone, or their combination (3 independent experiments).

Ingenol Mebutate purchased from MedChemExpress. Usage Cited in: Cell Rep Med. 2025 Jun 17;6(6):102146. [Abstract]

Ingenol Mebutate (IM). Kaplan-Meier analysis of overall survival (log rank test, n = 15 per group).

Ingenol Mebutate purchased from MedChemExpress. Usage Cited in: Cell Rep Med. 2025 Jun 17;6(6):102146. [Abstract]

Ingenol Mebutate (IM). Metastasis of nasopharyngeal carcinoma orthotopic xenografts of orthotopic mouse model was visualized using BLI, on day 14 (n = 15 per group).

Ingenol Mebutate purchased from MedChemExpress. Usage Cited in: Cell Rep Med. 2025 Jun 17;6(6):102146. [Abstract]

Ingenol Mebutate (IM). Immunohistochemistry analysis of PAS and CD31 double staining of orthotopic xenografts and ADAM10 and EMT-related marker expression in them. Quantification of VM, MV, and VM + MV numbers (H, n = 3 per group).

Ingenol Mebutate purchased from MedChemExpress. Usage Cited in: Cell Rep Med. 2025 Jun 17;6(6):102146. [Abstract]

Ingenol Mebutate (IM). Kaplan-Meier analysis of overall metastasis (log rank test, n = 15 per group).
EMBO J

ER-phagy restrains inflammatory responses through its receptor UBAC2. [Abstract]

2024 Nov;43(21):5057-5084. PMID: 39284914
Sci Data

High-throughput drug screening identifies novel therapeutics for Low Grade Serous Ovarian Carcinoma. [Abstract]

2024 Sep 19;11(1):1024. PMID: 39300112
J Proteome Res

Chemoproteomics Reveals FAM114A2 as a Functional Target of Wikstroelide E for Reversal of HIV-1 Latency. [Abstract]

2025 Oct 23. PMID: 41131870
bioRxiv

piTracer - Automatic reconstruction of molecular cascades for the identification of synergistic drug targets. [Abstract]

2023 Apr 9:2023.04.08.535933. PMID: 37066188

Lösungsmittel & Löslichkeit

In Vitro:

DMSO : ≥ 100 mg/mL (232.27 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

* "≥" means soluble, but saturation unknown.

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

2.3227 mL

11.6136 mL

23.2272 mL

5 mM

0.4645 mL

2.3227 mL

4.6454 mL

10 mM

0.2323 mL

1.1614 mL

2.3227 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

Stock Solution Working Solution

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline

Solubility: ≥ 2.5 mg/mL (5.81 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

Protocol 2

Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)

Solubility: ≥ 2.5 mg/mL (5.81 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil

Solubility: ≥ 2.5 mg/mL (5.81 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

%
DMSO +

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
%
+
+
%
Tween-80 + +
%
Saline +

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Working solution concentration: 0.22 mg/mL

Protokoll

Cell Assay^[2]

KG1a cells are transiently transfected with EGFP-tagged mouse PKC-δ subcloned into pEGFP-N1 plasmid using an Amaxa nucleofection apparatus. Cells are treated with Ingenol Mebutate (0.2 μM-20 μM) 24 hours after transfection. Cell viability in EGFP-positive cells is assessed and loss of viability confirmed in the total cell culture by MTT assay after 3 days. Briefly, 24 hours after transfection, 2 × 10⁴ cells are plated in 5 wells in 96-well plates and exposed to 0, 0.2, 2, and 20 μM Ingenol Mebutate. At 72 hours, 20 μL MTT substrate at 5 mg/mL is added and plates are incubated at 37°C. After 3 hours, 150 μL media is removed and replaced with 200 μL dimethyl sulfoxide (DMSO). Absorbance at an optical density (OD) of 550 nm is read on a plate reader and corrected for absorbance obtained from blank media controls^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (287 KB)
SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[1]. Kedei N, et al. Characterization of the interaction of ingenol 3-angelate with protein kinase C. Cancer Res. 2004 May 1;64(9):3243-55. [Content Brief]

[2]. Hampson P, et al. PEP005, a selective small-molecule activator of protein kinase C, has potent antileukemic activity mediated via the delta isoform of PKC. Blood. 2005 Aug 15;106(4):1362-8. [Content Brief]

[3]. Ghoul A, et al. Epithelial-to-mesenchymal transition and resistance to ingenol 3-angelate, a novel protein kinase C modulator, in colon cancer cells. Cancer Res. 2009 May 15;69(10):4260-9. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	2.3227 mL	11.6136 mL	23.2272 mL	58.0680 mL
	5 mM	0.4645 mL	2.3227 mL	4.6454 mL	11.6136 mL
	10 mM	0.2323 mL	1.1614 mL	2.3227 mL	5.8068 mL
	15 mM	0.1548 mL	0.7742 mL	1.5485 mL	3.8712 mL
	20 mM	0.1161 mL	0.5807 mL	1.1614 mL	2.9034 mL
	25 mM	0.0929 mL	0.4645 mL	0.9291 mL	2.3227 mL
	30 mM	0.0774 mL	0.3871 mL	0.7742 mL	1.9356 mL
	40 mM	0.0581 mL	0.2903 mL	0.5807 mL	1.4517 mL
	50 mM	0.0465 mL	0.2323 mL	0.4645 mL	1.1614 mL
	60 mM	0.0387 mL	0.1936 mL	0.3871 mL	0.9678 mL
	80 mM	0.0290 mL	0.1452 mL	0.2903 mL	0.7258 mL
	100 mM	0.0232 mL	0.1161 mL	0.2323 mL	0.5807 mL

Keywords

Ingenol Mebutate

5 Cited Publications

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Ingenol Mebutate

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Publications Citing Use of MedChemExpress (MCE) Ingenol Mebutate

Alle PKC Isoform-spezifische Produkte anzeigen

Biologische Aktivität

Chemical Information

Publications (5)

Lösungsmittel & Löslichkeit

Protokoll

Reinheit & Dokumentation

Verweise

Help & FAQs

Complete Stock Solution Preparation Table

Ingenol Mebutate Related Classifications

HY-B0719 Related Classifications