Coptisine chlorideCAS# 6020-18-4 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 6020-18-4 | SDF | Download SDF |
| PubChem ID | 72321 | Appearance | Orange powder |
| Formula | C19H14NO4Cl | M.Wt | 355.77 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | DMSO : 10.75 mg/mL (30.22 mM; Need ultrasonic and warming) | ||
| SMILES | C1C[N+]2=C(C=C3C=CC4=C(C3=C2)OCO4)C5=CC6=C(C=C51)OCO6.[Cl-] | ||
| Standard InChIKey | LUXPUVKJHVUJAV-UHFFFAOYSA-M | ||
| Standard InChI | InChI=1S/C19H14NO4.ClH/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14;/h1-2,5-8H,3-4,9-10H2;1H/q+1;/p-1 | ||
| 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 | Coptisine is an isoquinoline alkaloid isolated from Coptidis Rhizoma with anti-diabetic, antimicrobial, antiviral, anti-hepatoma, and anti-leukemia effects. Coptisine protects rat heart against myocardial ischemia/reperfusion injury by suppressing myocardial apoptosis and inflammation. Coptisine chloride can be absorbed across intestinal epithelial cells, and completely absorbed compounds. |
| In vitro | [Absorption of coptisine chloride and berberrubine across human intestinal epithelial by using human Caco-2 cell monolayers].[Pubmed: 18330249 ]Zhongguo Zhong Yao Za Zhi. 2007 Dec;32(23):2523-7.To study the absorption of Coptisine chloride (COP) and berberrubine (BRB) as chemical constituents of some traditional Chinese medicines in human intestinal epithelial.
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Coptisine chloride Dilution Calculator
Coptisine chloride Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.8108 mL | 14.054 mL | 28.108 mL | 56.2161 mL | 70.2701 mL |
| 5 mM | 0.5622 mL | 2.8108 mL | 5.6216 mL | 11.2432 mL | 14.054 mL |
| 10 mM | 0.2811 mL | 1.4054 mL | 2.8108 mL | 5.6216 mL | 7.027 mL |
| 50 mM | 0.0562 mL | 0.2811 mL | 0.5622 mL | 1.1243 mL | 1.4054 mL |
| 100 mM | 0.0281 mL | 0.1405 mL | 0.2811 mL | 0.5622 mL | 0.7027 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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Coptisine chloride is an alkaloid from Chinese goldthread, and acts as an efficient uncompetitive IDO inhibitor with a Ki value of 5.8 μM and an IC50 value of 6.3 μM.
In Vitro:Coptisine chloride is an efficient uncompetitive IDO inhibitor with a Ki value of 5.8 μM and an IC50 value of 6.3 μM[1]. Coptisine (0.1-100 μM) inhibits the proliferation of A549, H460, H2170, MDA-MB-231 and HT-29 cells, with IC50s of 18.09, 29.50, 21.60, 20.15 and 26.60 µM, respectively. Coptisine (12.5, 25, 50 μM) upregulates the expression of pH2AX and p21, reduces expression of cyclin B1, cdc2, and cdc25C, and induces G2/M arrest and apoptosis of A549 cells in a concentration-dependent manner. Coptisine (12.5, 25, 50 μM) also induces mitochondrial dysfunction and activates caspases activities in A549 cells. Furthermore, Coptisine (50 μM) increases ROS levels in a time-dependent manner (0.5, 1, 2, 4, 12, and 24 h)[3].
In Vivo:Coptisine shows increased toxicity in mice in a concentration dependent manner, with LD50 value of 880.18 mg/kg. Coptisine (154 mg/kg/day, 90 days) shows no toxicity on SD rats. Coptisine (23.35, 46.7, 70.05 mg/kg, p.o.) dose-dependently decreases the levels of TC, TG, and LDL-c and increases HDL-c content in serum of hamsters to different degree, slows down weight gain induced by the HFHC diet, and raises the level of cholesterol and TBA in feces dose-dependently in hamsters. Coptisine (70.05 mg/kg, p.o.) suppresses HMGCR protein expression level and induces the protein expression of SREBP-2, LDLR, and CYP7A1 involved in cholesterol metabolism[2].
References:
[1]. Yu D, et al. The IDO inhibitor coptisine ameliorates cognitive impairment in a mouse model of Alzheimer's disease. J Alzheimers Dis. 2015;43(1):291-302.
[2]. He K, et al. The safety and anti-hypercholesterolemic effect of coptisine in Syrian golden hamsters. Lipids. 2015 Feb;50(2):185-94.
[3]. Rao PC, et al. Coptisine-induced cell cycle arrest at G2/M phase and reactive oxygen species-dependent mitochondria-mediated apoptosis in non-small-cell lung cancer A549 cells. Tumour Biol. 2017 Mar;39(3):1010428317694565.
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[Absorption of coptisine chloride and berberrubine across human intestinal epithelial by using human Caco-2 cell monolayers].[Pubmed:18330249]
Zhongguo Zhong Yao Za Zhi. 2007 Dec;32(23):2523-7.
OBJECTIVE: To study the absorption of Coptisine chloride (COP) and berberrubine (BRB) as chemical constituents of some traditional Chinese medicines in human intestinal epithelial. METHOD: By using Caco-2 (the human colonic adenocarcinoma cell lines) cell monolayers as an intestinal epithelial cell model, the permeability of COP and BRB were studied from apical side (AP side) to basolateral side (BL side) or from BL side to AP side. The two alkaloids were measured by reversed-phase high performance liquid chromatography (HPLC) coupled with UV detector. Transport parameters and apparent permeability coefficients (P(app)) were then calculated and compared with those of propranolol and atenolol. P(app) values were also compared with the reported values for model compounds (propranolol and atenolol). RESULT: The P(app) values of COP, BRB were (1.103 +/- 0.162) x 10(-5), (1.309 +/- 0.102) x 10(-5) cm x s(-1 from AP side to BL side, and (0.300 +/- 0.041) x 10(-5) and (1.955 +/- 0.055) x 10(-5) cm x s(-1) from BL side to AP side, respectively. Their P(app) values were identical with those of propranolol [(2.23 +/- 0.10) x 10(-5 cm x s(-1)], which is a transcellular transport marker and as a control substance for high permeability. On the other hand, the efflux transport of BRB was higher 1.49 times more than its influx transport with 0.67 rate of P(app A-->B)/P(app B-->A). But P(app A-->B)/P(app B-->A value of COP was 3.67, which suggested that the efflux transport have not been involved in its absorbed mechanism in Caco-2 cells monolayers. CONCLUSION: COP and BRB can be absorbed across intestinal epithelial cells, and they are completely absorbed compounds. BRB may have been involved in efflux mechanism in Caco-2 cells monolayers model from the basolateral-to-apical direction.
