(-)-EburnamonineCAS# 4880-88-0 |
Quality Control & MSDS
3D structure
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| Cas No. | 4880-88-0 | SDF | Download SDF |
| PubChem ID | 71203 | Appearance | Powder |
| Formula | C19H22N2O | M.Wt | 294.4 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (15S,19S)-15-ethyl-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraen-17-one | ||
| SMILES | CCC12CCCN3C1C4=C(CC3)C5=CC=CC=C5N4C(=O)C2 | ||
| Standard InChIKey | WYJAPUKIYAZSEM-MOPGFXCFSA-N | ||
| Standard InChI | InChI=1S/C19H22N2O/c1-2-19-9-5-10-20-11-8-14-13-6-3-4-7-15(13)21(16(22)12-19)17(14)18(19)20/h3-4,6-7,18H,2,5,8-12H2,1H3/t18-,19+/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 | (-)-Eburnamonine induced a superior improvement than Papaverine of some clinical symptoms (motor disorders, retrograde amnesia, vertigo) and of cortical bioelectrical activity. (-)-Eburnamonine enhanced the affinities for carbachol, bethanechol, furmethide, methylfurmethide, pentylthio-TZTP, pilocarpine, oxotremorine and oxotremorine-M on the M2 receptors. | |||||
(-)-Eburnamonine Dilution Calculator
(-)-Eburnamonine Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.3967 mL | 16.9837 mL | 33.9674 mL | 67.9348 mL | 84.9185 mL |
| 5 mM | 0.6793 mL | 3.3967 mL | 6.7935 mL | 13.587 mL | 16.9837 mL |
| 10 mM | 0.3397 mL | 1.6984 mL | 3.3967 mL | 6.7935 mL | 8.4918 mL |
| 50 mM | 0.0679 mL | 0.3397 mL | 0.6793 mL | 1.3587 mL | 1.6984 mL |
| 100 mM | 0.034 mL | 0.1698 mL | 0.3397 mL | 0.6793 mL | 0.8492 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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15-Methylene-Eburnamonine Kills Leukemic Stem Cells and Reduces Engraftment in a Humanized Bone Marrow Xenograft Mouse Model of Leukemia.[Pubmed:27677525]
ChemMedChem. 2016 Nov 7;11(21):2392-2397.
Recent studies suggest that leukemia stem cells (LSCs) play a critical role in the initiation, propagation, and relapse of leukemia. Herein we show that (-)-15-methylene-eburnamonine, a derivative of the alkaloid (-)-Eburnamonine, is cytotoxic against acute and chronic lymphocytic leukemias (ALL and CLL) and acute myelogenous leukemia (AML). The agent also decreases primary LSC frequency in vitro. The cytotoxic effects appear to be mediated via the oxidative stress pathways. Furthermore, we show that the compound kills AML, ALL, and CLL stem cells. By the use of a novel humanized bone marrow murine model of leukemia (huBM/NSG), it was found to decrease progenitor cell engraftment.
Two new indole alkaloids from Hunteria zeylanica.[Pubmed:26667775]
J Asian Nat Prod Res. 2016;18(4):349-53.
Two new indole alkaloids, 14beta-hydroperoxy-eburnamine (1) and 18alpha-hydroxy-eburnamine (2), together with three known indole alkaloids, (-)-Eburnamonine (3), (-)-eburnamenine (4), and eburnamine (5) were isolated from Hunteria zeylanica collected in Hainan Province of China. Their structures were determined by spectroscopic analysis. The relative configuration of 2 was deduced by NOE experiment and evidenced by the calculations for energy minimization with the molecular modeling program Chem3D Ultra 10.0.
Synthesis of 15-methylene-eburnamonine from (+)-vincamine, evaluation of anticancer activity, and investigation of mechanism of action by quantitative NMR.[Pubmed:24055047]
Bioorg Med Chem Lett. 2013 Nov 1;23(21):5865-9.
The biological role of installing a critical exocyclic enone into the structure of the alkaloid, (-)-Eburnamonine, and characterization of the new chemical reactivity by quantitative NMR without using deuterated solvents are described. This selective modification to a natural product imparts potent anticancer activity as well as bestows chemical reactivity toward nucleophilic thiols, which was measured by quantitative NMR. The synthetic strategy provides an overall conversion of 40%. In the key synthetic step, a modified Peterson olefination was accomplished through the facile release of trifluoroacetate to create the requisite enone in the presence of substantial steric hindrance.
Determination of the absolute configuration of 19-OH-(-)-eburnamonine using a combination of residual dipolar couplings, DFT chemical shift predictions, and chiroptics.[Pubmed:22816295]
Nat Prod Commun. 2012 Jun;7(6):735-8.
19-OH-(-)-Eburnamonine 1 is a new indole alkaloid isolated from Bonafusia macrocalyx. A natural derivative from (-)-Eburnamonine for which absolute configuration and conformation has been determined by making use of residual dipolar couplings enhanced NMR, circular dichroism spectra and high-level computations.
Exploiting the facile release of trifluoroacetate for the alpha-methylenation of the sterically hindered carbonyl groups on (+)-sclareolide and (-)-eburnamonine.[Pubmed:21491928]
J Org Chem. 2011 May 20;76(10):3676-83.
An efficient method for the alpha-methylenation of carbonyl groups is reported, and this transformation is accomplished by a facile elimination of trifluoroacetate during the formation of the olefin. This method represents an improvement beyond existing protocol in cases of steric hindrance, and we have demonstrated the utility of the process across a series of ketones, lactams, and lactones. Additionally, we have applied this method to produce semisynthetic derivatives of the natural products (+)-sclareolide and (-)-Eburnamonine, in which the carbonyl group is proximal to bulky functional groups. Mechanistic insight is also provided from a time course of (19)F NMR. Biological evaluation of the natural-product-derived enones led to the identification of a derivative of (-)-Eburnamonine with significant cytotoxicity (LC(50) = 14.12 muM) in drug-resistant MDA-MB-231 breast cancer cells.
