IngenolCAS# 30220-46-3 |
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| Cas No. | 30220-46-3 | SDF | Download SDF |
| PubChem ID | 442042 | Appearance | White powder |
| Formula | C20H28O5 | M.Wt | 348.44 |
| Type of Compound | Diterpenoids | Storage | Desiccate at -20°C |
| Synonyms | (-)-Ingenol | ||
| Solubility | DMSO : 100 mg/mL (287.00 mM; Need ultrasonic) | ||
| SMILES | CC1CC2C(C2(C)C)C3C=C(C(C4(C1(C3=O)C=C(C4O)C)O)O)CO | ||
| Standard InChIKey | VEBVPUXQAPLADL-POYOOMFHSA-N | ||
| Standard InChI | InChI=1S/C20H28O5/c1-9-7-19-10(2)5-13-14(18(13,3)4)12(17(19)24)6-11(8-21)16(23)20(19,25)15(9)22/h6-7,10,12-16,21-23,25H,5,8H2,1-4H3/t10-,12+,13-,14+,15+,16-,19+,20-/m1/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| 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 | Reactivation of HIV latency by a newly modified Ingenol derivative via protein kinase Cδ-NF-κB signaling.[Pubmed: 24804860]AIDS. 2014 Jul 17;28(11):1555-66.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. |
| In vivo | Clinical Response to Ingenol Mebutate in Patients With Actinic Keratoses.[Pubmed: 26055975]Actas Dermosifiliogr. 2015 Jun 5.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.
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| Cell Research | Ingenol derivatives inhibit proliferation and induce apoptosis in breast cancer cell lines.[Pubmed: 16285571]Eur J Gynaecol Oncol. 2005;26(5):526-30.
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| 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. |
Ingenol Dilution Calculator
Ingenol Molarity Calculator
| 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 necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Ingenol is a PKC activator, with a Ki of 30 μM, with antitumor activity.
In Vitro:Ingenol is a PKC activator, with a Ki of 30 μM. Ingenol induces ornithine decarboxylase activity (1, 3 mM), and causes morphological changes (1 mM) in primary mouse epidermal keratinocytes. Ingenol (125 μM, 250 μM, 500 μM, 1 mM) also inhibits cell-cell communication[1].
References:
[1]. Hasler CM, et al. Specific binding to protein kinase C by ingenol and its induction of biological responses. Cancer Res. 1992 Jan 1;52(1):202-8.
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Syntheses, biological evaluation and SAR of ingenol mebutate analogues for treatment of actinic keratosis and non-melanoma skin cancer.[Pubmed:23993332]
Bioorg Med Chem Lett. 2013 Oct 15;23(20):5624-9.
Ingenol mebutate is the active ingredient in Picato(R) 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. 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. 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.
Synthesis, biological evaluation and SAR of 3-benzoates of ingenol for treatment of actinic keratosis and non-melanoma skin cancer.[Pubmed:24332494]
Bioorg Med Chem Lett. 2014 Jan 1;24(1):54-60.
Ingenol 3-benzoates were investigated with respect to chemical stability, pro-inflammatory effects, cell death induction and PKCdelta activation. A correlation between structure, chemical stability and biological activity was found and compared to Ingenol mebutate (Ingenol 3-angelate) used for field treatment of actinic keratosis. We also provided further support for involvement of PKCdelta for induction of oxidative burst and cytokine release. Molecular modeling and dynamics calculations corroborated the essential interactions between key compounds and C1 domain of PKCdelta.
Ingenol derivatives inhibit proliferation and induce apoptosis in breast cancer cell lines.[Pubmed:16285571]
Eur J Gynaecol Oncol. 2005;26(5):526-30.
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. 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.
Reactivation of HIV latency by a newly modified Ingenol derivative via protein kinase Cdelta-NF-kappaB signaling.[Pubmed:24804860]
AIDS. 2014 Jul 17;28(11):1555-66.
OBJECTIVE: 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. DESIGN: 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: 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. RESULTS: 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)delta-nuclear factor kappa-light-chain-enhancer of activated B cells (NF-kappaB) pathway and directly inducing NF-kappaB 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.
Clinical Response to Ingenol Mebutate in Patients With Actinic Keratoses.[Pubmed:26055975]
Actas Dermosifiliogr. 2015 Dec;106(10):e55-61.
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. 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. 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.
