Coptisine chloride: Overview, Structure, Properties, and Formulas

Coptisine, Q-100696, or NSC-119754, is an isoquinoline-alkaloid that was secluded from Coptidis Rhizoma. It has against diabetic just as antimicrobial properties and furthermore antiviral, antiviral, and hostile to hepatoma attributes. Coptisine Chloride is a viable non-serious IDO inhibitor with an IC50 worth of 6.3 millimeters and Ki levels of 5.8 millimoles. For purchasing these synthetic compounds and other examination synthetic substances numerous web-based stores are accessible. From any store, you can buy chemicals online.

IUPAC name

5,7,17,19-tetraoxa-13-azoniahexacyclo[11.11.0.0^2,10.0^4,8.0^15,23.0^16,20]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	Activity Value, µM	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	For acquiring a higher dissolvability, please warm the cylinder at 37 ℃ and shake it in the ultrasonic shower for a while.The stock arrangement can be put away underneath - 20℃ for quite some time.   We suggest that you plan and utilize the arrangement around the same time. Notwithstanding, if the test plan requires, the stock arrangements can be ready ahead of time, and the stock arrangement should be fixed and put away beneath - 20℃. As a general rule, the stock arrangement can be saved for a long time.   Prior to utilization, we suggest that you leave the vial at room temperature for somewhere around an hour prior to opening it.

 

Biological activity 

 

Description

Coptisine is an isoquinoline alkaloid secluded from Coptidis Rhizoma with hostile to diabetic, antimicrobial, antiviral, against hepatoma, and against leukemia impacts. Coptisine ensures the rodent heart against myocardial ischemia/reperfusion injury by stifling myocardial apoptosis and irritation. Coptisine chloride can be retained across digestive epithelial cells and totally ingested 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 utilizing Caco-2 (the human colonic adenocarcinoma cell lines) cell monolayers as a gastrointestinal epithelial cell model, the penetrability of Coptisine chloride and BRB were contemplated from the apical side (AP side) to basolateral side (BL side) or from BL side to AP side. The two alkaloids were estimated by turned around stage elite execution fluid chromatography (HPLC) combined with a UV indicator. Transport boundaries and clear penetrability coefficients (P(app)) were then determined and contrasted and those of propranolol and atenolol. P(app) values were likewise contrasted and the announced qualities for model mixtures (propranolol and atenolol). The P(app) upsides 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, separately. Their P(app) values were indistinguishable 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 porousness. Then again, the efflux transport of BRB was higher 1.49 occasions more than its deluge transport with a 0.67 pace of P(app A- - >B)/P(app B- - >A). Yet, P(app A- - >B)/P(app B- - >A worth of Coptisine chloride was 3.67, which recommended that the efflux transport has not been engaged with its retained instrument 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.