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Ingenol
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Product Name Ingenol
Price: $70 / 20mg
CAS No.: 30220-46-3
Catalog No.: CFN90187
Molecular Formula: C20H28O5
Molecular Weight: 348.44 g/mol
Purity: >=98%
Type of Compound: Diterpenoids
Physical Desc.: White powder
Source: The seeds of Euphorbia lathyris L.
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download: COA    MSDS    SDF    Manual
Similar structural: Comparison (Web)  (SDF)
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According to end customer requirements, ChemFaces provide solvent format. This solvent format of product intended use: Signaling Inhibitors, Biological activities or Pharmacological activities.
Size /Price /Stock 10 mM * 1 mL in DMSO / $18.0 / In-stock
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Related Screening Libraries
Size /Price /Stock 10 mM * 100 uL in DMSO / Inquiry / In-stock
10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries
Biological Activity
Description: Ingenol derivatives inhibit proliferation and induce apoptosis in breast cancer cell lines, formulating novel derivatives from Ingenol esters may be an innovative approach to develop new lead compounds to reactivate latent HIV. Ingenol mebutate is an effective treatment for actinic keratosis.
Targets: HIV | PKC | NF-kB | gp120/CD4
In vitro:
AIDS. 2014 Jul 17;28(11):1555-66.
Reactivation of HIV latency by a newly modified Ingenol derivative via protein kinase Cδ-NF-κB signaling.[Pubmed: 24804860]
Although HAART effectively suppresses viral replication, it fails to eradicate latent viral reservoirs. The 'shock and kill' strategy involves the activation of HIV from latent reservoirs and targeting them for eradication. Our goal was to develop new approaches for activating HIV from latent reservoirs. We investigated capacity of Ingenol B (IngB), a newly modified derivative of Ingenol ester that was originally isolated from a Brazilian plant in Amazon, for its capacity and mechanisms of HIV reactivation.
METHODS AND RESULTS:
Reactivation of HIV-1 by IngB was evaluated in J-Lat A1 cell culture model of HIV latency as well as in purified primary CD4 T cells from long-term HAART-treated virologically-suppressed HIV-infected individuals. The underlining molecular mechanisms of viral reactivation were investigated using flow cytometry, RT-qPCR and chromatin immunoprecipitation. IngB is highly effective in reactivating HIV in J-Lat A1 cells with relatively low cellular toxicity. It is also able to reactivate latent HIV in purified CD4 T cells from HAART-treated HIV-positive individuals ex vivo. Our data show that IngB may reactivate HIV expression by both activating protein kinase C (PKC)δ-nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) pathway and directly inducing NF-κB protein expression. Importantly, IngB has a synergistic effect with JQ1, a BET bromodomain inhibitor, in latent HIV reactivation.
CONCLUSIONS:
IngB is a new promising compound to activate latent HIV reservoirs. Our data suggest that formulating novel derivatives from Ingenol esters may be an innovative approach to develop new lead compounds to reactivate latent HIV.
In vivo:
Actas Dermosifiliogr. 2015 Jun 5.
Clinical Response to Ingenol Mebutate in Patients With Actinic Keratoses.[Pubmed: 26055975]
Cryotherapy is the most common treatment for actinic keratosis, but its effect is limited to individual lesions. Several topical drugs, however, are available that, in addition to treating individual actinic keratoses, target field cancerization and thereby act on subclinical lesions. Examples are 5-fluorouracil, imiquimod, diclofenac, and Ingenol mebutate.
METHODS AND RESULTS:
We report on 17 patients with actinic keratoses treated with Ingenol mebutate and describe our findings on treatment effectiveness, adherence, and tolerance. Complete and partial response rates were 35% and 53%, respectively. Ninety-four percent of patients fully adhered to treatment and 18% developed severe local reactions.
CONCLUSIONS:
Ingenol mebutate is an effective treatment for actinic keratosis. Although it has a similar rate of local reactions to other treatments available for actinic keratosis, its short treatment regimen favors better adherence.
Ingenol Description
Source: The seeds of Euphorbia lathyris L.
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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Recently, ChemFaces products have been cited in many studies from excellent and top scientific journals

Cell. 2018 Jan 11;172(1-2):249-261.e12.
doi: 10.1016/j.cell.2017.12.019.
IF=36.216(2019)

PMID: 29328914

Cell Metab. 2020 Mar 3;31(3):534-548.e5.
doi: 10.1016/j.cmet.2020.01.002.
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ACS Nano. 2018 Apr 24;12(4): 3385-3396.
doi: 10.1021/acsnano.7b08969.
IF=13.903(2019)

PMID: 29553709

Nature Plants. 2016 Dec 22;3: 16206.
doi: 10.1038/nplants.2016.205.
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PMID: 28005066

Sci Adv. 2018 Oct 24;4(10): eaat6994.
doi: 10.1126/sciadv.aat6994.
IF=12.804(2019)

PMID: 30417089
Calculate Dilution Ratios(Only for Reference)
1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8699 mL 14.3497 mL 28.6993 mL 57.3987 mL 71.7484 mL
5 mM 0.574 mL 2.8699 mL 5.7399 mL 11.4797 mL 14.3497 mL
10 mM 0.287 mL 1.435 mL 2.8699 mL 5.7399 mL 7.1748 mL
50 mM 0.0574 mL 0.287 mL 0.574 mL 1.148 mL 1.435 mL
100 mM 0.0287 mL 0.1435 mL 0.287 mL 0.574 mL 0.7175 mL
* Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
Protocol
Cell Research:
Eur J Gynaecol Oncol. 2005;26(5):526-30.
Ingenol derivatives inhibit proliferation and induce apoptosis in breast cancer cell lines.[Pubmed: 16285571]

METHODS AND RESULTS:
We present an analysis of the antitumour effects of a library of Ingenol derivatives synthesized in our laboratory and published elsewhere. Fluoro-Ingenol (1), Ingenol-20-deoxy-20-phtalimido (2), Ingenol-3-benzoate-20-deoxy-20-benzamide (3), Ingenol-3-benzoate (4), Ingenol-3,5-dibenzoate (5), Ingenol-3,20-dibenzoate (6), 20-deoxy-20-benylureidoIngenol-3-benzoate (7), Ingenol-20-deoxy-20-fluoro-3-benzoate (8), Ingenol-20-deoxy-20-fluoro-3,5-dibenzoate (9), Ingenol-20-phenylcarbamate (10), Ingenol-20-benzoate (11), Ingenol-3-benzoate-20-phenylcarbamate (12) were tested in vitro on two well characterized breast cancer cell (BCC) lines, namely T47D and MDA-MB-231, as representative of two opposite types of hormone-sensitiveness and differentiation stage.
CONCLUSIONS:
These experiments led us to identify Ingenol-20-benzoate (11) as a promising antitumour compound characterized by a relevant inhibition of cell growth and apoptotic cell death involving a p53-mediated pathway.
Structure Identification:
Bioorg Med Chem Lett. 2013 Oct 15;23(20):5624-9.
Syntheses, biological evaluation and SAR of ingenol mebutate analogues for treatment of actinic keratosis and non-melanoma skin cancer.[Pubmed: 23993332]
Ingenol mebutate is the active ingredient in Picato® a new drug for the treatment of actinic keratosis. A number of derivatives related to Ingenol mebutate were prepared by chemical synthesis from Ingenol with the purpose of investigating the SAR and potency in assays relating to pro-inflammatory effects (induction of PMN oxidative burst and keratinocyte cytokine release), the potential of cell death induction, as well as the chemical stability.
METHODS AND RESULTS:
By modifications of the Ingenol scaffold several prerequisites for activity were identified. The chemical stability of the compounds could be linked to an acyl migration mechanism.
CONCLUSIONS:
We were able to find analogues of Ingenol mebutate with comparable in vitro properties. Some key features for potent and more stable Ingenol derivatives have been identified.
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