Health and Fitness

Coptisine chloride: Overview, Structure, Properties, and Formulas

Coptisine, Q-100696, or NSC-119754, is an isoquinoline-alkaloid that was isolated from Coptidis Rhizoma. It has anti-diabetic as well as antimicrobial properties and also antiviral, antiviral, and anti-hepatoma characteristics. Coptisine Chloride is an effective non-competitive IDO inhibitor with an IC50 value of 6.3 millimeters and Ki levels of 5.8 millimoles. For buying these chemicals and other research chemicals many online stores are available. From any store, you can buy chemicals online.

IUPAC name

5,7,17,19-tetraoxa-13-azoniahexacyclo[11.11.0.02,10.04,8.015,23.016,20]tetracosa-1(13),2,4(8),9,14,16(20),21,23-octaene;chloride

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

InChI Key

 

LUXPUVKJHVUJAV-UHFFFAOYSA-M

Properties

 

Property Name Property Value Reference
Molecular Weight 355.8 Computed by PubChem 2.1 (PubChem release 2021.05.07)
Hydrogen Bond Donor Count 0 Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Hydrogen Bond Acceptor Count 5 Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Rotatable Bond Count 0 Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Exact Mass 355.0611356 Computed by PubChem 2.1 (PubChem release 2021.05.07)
Monoisotopic Mass 355.0611356 Computed by PubChem 2.1 (PubChem release 2021.05.07)
Topological Polar Surface Area 40.8 Ų Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Heavy Atom Count 25 Computed by PubChem
Formal Charge 0 Computed by PubChem
Complexity 502 Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Isotope Atom Count 0 Computed by PubChem
Defined Atom Stereocenter Count 0 Computed by PubChem
Undefined Atom Stereocenter Count 0 Computed by PubChem
Defined Bond Stereocenter Count 0 Computed by PubChem
Undefined Bond Stereocenter Count 0 Computed by PubChem
Covalently-Bonded Unit Count 2 Computed by PubChem
Compound Is Canonicalized Yes Computed by PubChem (release 2021.05.07)

Biological Tests Results

 

Activity Value, µM Activity Activity Type Target Name BioAssay Name
Active 3.3 GI50 Antiproliferative activity against rat VSMC assessed as cell growth inhibition
Active 3.35 GI50 Growth inhibition against rat VSMC after 72 hrs by MTT assay
Active 4.49 GI50 Growth inhibition against rat A10 cells after 72 hrs by MTT assay
Active 5.59 IC50 Cytotoxicity against human HCT8 cells assessed as growth inhibition rate after 96 hrs by MTT assay

 

Chemicals properties 

 

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 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℃.

 

Biological activity 

 

Description Coptisine is an isoquinoline alkaloid isolated from Coptidis Rhizoma with anti-diabetic, antimicrobial, antiviral, anti-hepatoma, and anti-leukemia effects. It 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].

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.
METHODS AND RESULTS:
By using Caco-2 (the human colonic adenocarcinoma cell lines) cell monolayers as an intestinal epithelial cell model, the permeability of Coptisine chloride and BRB were studied from apical side (AP side) to basolateral side (BL side) or from BL side to AP side.

The P(app) values of Coptisine chloride, 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 Coptisine chloride was 3.67, which suggested that the efflux transport have not been involved in its absorbed mechanism in Caco-2 cells monolayers.

Conclusion

Coptisine chloride can be absorbed through intestinal epithelial cells. Thus, BRB may have been involved in the efflux mechanism in the Caco-2 cells monolayers model from the basolateral-to-apical direction.

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