(-)-AnonaineCAS# 1862-41-5 |
2D Structure
Quality Control & MSDS
3D structure
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Number of papers citing our products
Cas No. | 1862-41-5 | SDF | Download SDF |
PubChem ID | 160597 | Appearance | Powder |
Formula | C17H15NO2 | M.Wt | 265.31 |
Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
SMILES | C1CNC2CC3=CC=CC=C3C4=C2C1=CC5=C4OCO5 | ||
Standard InChIKey | VZTUKBKUWSHDFM-CYBMUJFWSA-N | ||
Standard InChI | InChI=1S/C17H15NO2/c1-2-4-12-10(3-1)7-13-15-11(5-6-18-13)8-14-17(16(12)15)20-9-19-14/h1-4,8,13,18H,5-7,9H2/t13-/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 | 1. (-)-Anonaine has some anticancer activity, it induces apoptosis through Bax- and caspase-dependent pathways in human cervical cancer (HeLa) cells. 2. (-)-Anonaine may be considered a potent compound for chemotherapy against cervical cancer or a health food supplement for cancer chemoprevention. 3. (-)-Anonaine has vasorelaxant effect. 4. (-)-Anonaine induces DNA damage and inhibits growth and migration of human lung carcinoma h1299 cells. |
Targets | Bcl-2/Bax | Caspase | p53 | PARP | PDE | Calcium Channel |
(-)-Anonaine Dilution Calculator
(-)-Anonaine Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 3.7692 mL | 18.8459 mL | 37.6918 mL | 75.3835 mL | 94.2294 mL |
5 mM | 0.7538 mL | 3.7692 mL | 7.5384 mL | 15.0767 mL | 18.8459 mL |
10 mM | 0.3769 mL | 1.8846 mL | 3.7692 mL | 7.5384 mL | 9.4229 mL |
50 mM | 0.0754 mL | 0.3769 mL | 0.7538 mL | 1.5077 mL | 1.8846 mL |
100 mM | 0.0377 mL | 0.1885 mL | 0.3769 mL | 0.7538 mL | 0.9423 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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(-)-Anonaine induces apoptosis through Bax- and caspase-dependent pathways in human cervical cancer (HeLa) cells.[Pubmed:18524447]
Food Chem Toxicol. 2008 Aug;46(8):2694-702.
(-)-Anonaine has been shown to have some anticancer activities, but the mechanisms of (-)-Anonaine inducing cell death of human cancer cells is not fully understood. We investigated the mechanisms of apoptosis induced by (-)-Anonaine in human HeLa cancer cells. Treatment with (-)-Anonaine induces dose-dependent DNA damage that is correlated with increased intracellular nitric oxide, reactive oxygen species, glutathione depletion, disruptive mitochondrial transmembrane potential, activation of caspase 3, 7, 8, and 9, and poly ADP ribose polymerase cleavage. Our data indicate that (-)-Anonaine up-regulated the expression of Bax and p53 proteins in HeLa cancer cells. The apoptosis and expression of Bax induced by (-)-Anonaine could be inhibited when the HeLa cells were pretreated with Boc-Asp(OMe)-fmk, which is a broad caspases inhibitor. There was no obvious DNA damage in the (-)-Anonaine-treated Madin-Darby canine kidney and Vero cell lines. Both Madin-Darby canine kidney and Vero cell lines are kidney epithelial cellular morphology. These results suggest that (-)-Anonaine might be considered a potent compound for chemotherapy against cervical cancer or a health food supplement for cancer chemoprevention.
(-)-Anonaine induces DNA damage and inhibits growth and migration of human lung carcinoma h1299 cells.[Pubmed:21361287]
J Agric Food Chem. 2011 Mar 23;59(6):2284-90.
The anticancer effects of (-)-Anonaine were investigated in this current study. (-)-Anonaine at concentration ranges of 50-200 muM exhibited significant inhibition to cell growth and migration activities on human lung cancer H1299 cells at 24 h, albeit cell cycle analyses showed that (-)-Anonaine at the above concentration ranges did not cause any significant changes in cell-cycle distributions. Significant nuclear damages of H1299 cells were observed with 10-200 muM (-)-Anonaine treatment in a comet assay, whereas higher concentrations (6 and 30 mM) of (-)-Anonaine concentrations were required to cause DNA damages in an in vitro plasmid cleavage assay. In summary, our results demonstrated that (-)-Anonaine exhibited dose-dependent antiproliferatory, antimigratory, and DNA-damaging effects on H1299 cells. We inferred that (-)-Anonaine can cause cell-cycle arrest and DNA damage to hamper the physiological behavior of cancer cells at 72 h, and therefore, it can be useful as one of the potential herbal supplements for chemoprevention of human lung cancer.
Vascular activity of (-)-anonaine, (-)-roemerine and (-)-pukateine, three natural 6a(R)-1,2-methylenedioxyaporphines with different affinities for alpha1-adrenoceptor subtypes.[Pubmed:15254852]
Planta Med. 2004 Jul;70(7):603-9.
We have studied the mechanism of action of three 6a( R)-1,2-methylenedioxyaporphines as vasorelaxant compounds. The alkaloids assayed showed different affinities for the three human cloned alpha (1)-adrenoceptor (AR) subtypes stably expressed in rat-1 fibroblasts, showing lower affinity for alpha(1B)-AR with regard to the alpha(1A)- or alpha(1D)-subtypes. These three natural compounds are more potent inhibitors of [ (3)H]-prazosin binding than of [ (3)H]-diltiazem binding to rat cerebral cortical membranes. As all these alkaloids inhibited noradrenaline (NA)-induced [ (3)H]-inositol phosphate formation in cerebral cortex and rat tail artery, they may be safely viewed as alpha (1)-AR antagonists, as is demonstrated by the vasorelaxant responses observed in isolated rat tail artery and/or aorta precontracted with NA. The alkaloids also inhibited the contractile response evoked by KCl (80 mM) but with a lower potency than that shown against NA-induced contraction. We have also examined their ability to inhibit the different forms of cyclic nucleotide phosphodiesterases (PDE) isolated from bovine aortic smooth muscle and endothelial cells, with negative results. We conclude that N-methylation favours the interaction of (R)-aporphines with all alpha (1)-AR subtypes, and that the topography of the binding site recognizing the basic or protonated nitrogen atom is similar in all three alpha (1)-AR subtypes. The presence of a hydroxy group at C-11 has different effects on the affinity for each alpha (1)-AR subtype but decreases the affinity for Ca (2+) channels. These results confirm and extend the view that subtle changes in the hydroxylation patterns on the aromatic ring of the aporphine structure affect the interactions of these compounds with the three alpha (1)-AR subtypes in different ways, suggesting that the binding site recognizing the aporphine skeleton is different in each of the three subtypes.