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MedKoo Cat#: 540088 | Name: Coptisine chloride
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Coptisine Cl is a MAO-A inhibitor found in a variety of plant sources. It attenuates mitochondrial respiratory dysfunction, inhibits expression of RhoA and ROCK, suppresses proliferation of hepatoma and leukemia cells, and decreases myocardial apoptosis.

Chemical Structure

Coptisine chloride
CAS#6020-18-4 (chloride)

Theoretical Analysis

MedKoo Cat#: 540088

Name: Coptisine chloride

CAS#: 6020-18-4 (chloride)

Chemical Formula: C19H14ClNO4

Exact Mass: 355.0611

Molecular Weight: 355.77

Elemental Analysis: C, 64.14; H, 3.97; Cl, 9.96; N, 3.94; O, 17.99

Price and Availability

Size Price Availability Quantity
25mg USD 350.00 2 Weeks
50mg USD 550.00 2 Weeks
100mg USD 850.00 2 Weeks
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Related CAS #
3486-66-6 (cation) 6020-18-4 (chloride)
Synonym
Coptisine chloride; Coptisin Chloride; Q-100696; Q100696; Q 100696; NSC-119754; NSC119754; NSC 119754;
IUPAC/Chemical Name
6,7-dihydro-[1,3]dioxolo[4',5':7,8]isoquinolino[3,2-a][1,3]dioxolo[4,5-g]isoquinolin-5-ium chloride
InChi Key
LUXPUVKJHVUJAV-UHFFFAOYSA-M
InChi Code
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
SMILES Code
C1(C(CC[N+]2=C1C=C(C=C3)C(C4=C3OCO4)=C2)=C5)=CC6=C5OCO6.[Cl-]
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Coptisine chloride acts as an efficient uncompetitive IDO inhibitor with a Ki value of 5.8 μM and an IC50 value of 6.3 μM. Coptisine chloride is a potent H1N1 neuraminidase (NA-1) inhibitor with an IC50 of 104.6 μg/mL.
In vitro activity:
Results showed that COP (coptisine) inhibited the cell viability and proliferation of EC cells, and COP induced G2/M phase arrest of EC cells and decreased the expression of claudin-2, p-cdc2, CDK1 and cyclin B1. Reference: Pharmazie. 2021 May 1;76(5):202-207. https://pubmed.ncbi.nlm.nih.gov/33964993/
In vivo activity:
The impaired EDRs in aortas from these diabetic (DM) mice were enhanced by coptisine treatment (1 µM, 16 h) (Figure 3A) whilst SNP-induced endothelium-independent relaxations remained unaltered (Figure 3B). Reference: Molecules. 2021 Jul; 26(14): 4210. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8303502/
Solvent mg/mL mM comments
Solubility
DMSO 4.0 11.24
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 355.77 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Wen X, Zhang X, Qu S, Chen X, Liu C, Yang Y. Coptisine induces G2/M arrest in esophageal cancer cell via the inhibition of p38/ERK1/2/claudin-2 signaling pathway. Pharmazie. 2021 May 1;76(5):202-207. doi: 10.1691/ph.2021.1353. PMID: 33964993. 2. Kim SY, Hwangbo H, Kim MY, Ji SY, Lee H, Kim GY, Kwon CY, Leem SH, Hong SH, Cheong J, Choi YH. Coptisine induces autophagic cell death through down-regulation of PI3K/Akt/mTOR signaling pathway and up-regulation of ROS-mediated mitochondrial dysfunction in hepatocellular carcinoma Hep3B cells. Arch Biochem Biophys. 2021 Jan 15;697:108688. doi: 10.1016/j.abb.2020.108688. Epub 2020 Nov 21. PMID: 33227289. 3. Zhou Y, Zhou C, Zhang X, Vong CT, Wang Y, Cheang WS. Coptisine Attenuates Diabetes-Associated Endothelial Dysfunction through Inhibition of Endoplasmic Reticulum Stress and Oxidative Stress. Molecules. 2021 Jul 11;26(14):4210. doi: 10.3390/molecules26144210. PMID: 34299486; PMCID: PMC8303502. 4. Wang Y, Liu J, Huang Z, Li Y, Liang Y, Luo C, Ni C, Xie J, Su Z, Chen J, Li C. Coptisine ameliorates DSS-induced ulcerative colitis via improving intestinal barrier dysfunction and suppressing inflammatory response. Eur J Pharmacol. 2021 Apr 5;896:173912. doi: 10.1016/j.ejphar.2021.173912. Epub 2021 Jan 27. PMID: 33508280.
In vitro protocol:
1. Wen X, Zhang X, Qu S, Chen X, Liu C, Yang Y. Coptisine induces G2/M arrest in esophageal cancer cell via the inhibition of p38/ERK1/2/claudin-2 signaling pathway. Pharmazie. 2021 May 1;76(5):202-207. doi: 10.1691/ph.2021.1353. PMID: 33964993. 2. Kim SY, Hwangbo H, Kim MY, Ji SY, Lee H, Kim GY, Kwon CY, Leem SH, Hong SH, Cheong J, Choi YH. Coptisine induces autophagic cell death through down-regulation of PI3K/Akt/mTOR signaling pathway and up-regulation of ROS-mediated mitochondrial dysfunction in hepatocellular carcinoma Hep3B cells. Arch Biochem Biophys. 2021 Jan 15;697:108688. doi: 10.1016/j.abb.2020.108688. Epub 2020 Nov 21. PMID: 33227289.
In vivo protocol:
1. Zhou Y, Zhou C, Zhang X, Vong CT, Wang Y, Cheang WS. Coptisine Attenuates Diabetes-Associated Endothelial Dysfunction through Inhibition of Endoplasmic Reticulum Stress and Oxidative Stress. Molecules. 2021 Jul 11;26(14):4210. doi: 10.3390/molecules26144210. PMID: 34299486; PMCID: PMC8303502. 2. Wang Y, Liu J, Huang Z, Li Y, Liang Y, Luo C, Ni C, Xie J, Su Z, Chen J, Li C. Coptisine ameliorates DSS-induced ulcerative colitis via improving intestinal barrier dysfunction and suppressing inflammatory response. Eur J Pharmacol. 2021 Apr 5;896:173912. doi: 10.1016/j.ejphar.2021.173912. Epub 2021 Jan 27. PMID: 33508280.
1: Yu D, Tao BB, Yang YY, Du LS, Yang SS, He XJ, Zhu YW, Yan JK, Yang Q. The IDO inhibitor coptisine ameliorates cognitive impairment in a mouse model of Alzheimer's disease. J Alzheimers Dis. 2015;43(1):291-302. doi: 10.3233/JAD-140414. PubMed PMID: 25079795. 2: He K, Ye X, Wu H, Wang Y, Zou Z, Ning N, Hu Y, Chen B, Fang X, Li X. The safety and anti-hypercholesterolemic effect of coptisine in Syrian golden hamsters. Lipids. 2015 Feb;50(2):185-94. doi: 10.1007/s11745-014-3983-7. Epub 2014 Dec 30. PubMed PMID: 25547428. 3: Lee JW, Iwahashi A, Hasegawa S, Yonezawa T, Jeon WB, Cha BY, Nagai K, Woo JT. Coptisine inhibits RANKL-induced NF-κB phosphorylation in osteoclast precursors and suppresses function through the regulation of RANKL and OPG gene expression in osteoblastic cells. J Nat Med. 2012 Jan;66(1):8-16. doi: 10.1007/s11418-011-0537-7. Epub 2011 Jun 9. PubMed PMID: 21656335. 4: Zhang ZH, Deng AJ, Yu JQ, Li ZH, Wu LQ, Wang WJ, Qin HL. [Advance in studies on pharmacological activity of coptisine hydrochloride]. Zhongguo Zhong Yao Za Zhi. 2013 Sep;38(17):2750-4. Chinese. PubMed PMID: 24380292. 5: Zhang X, Qiu F, Jiang J, Gao C, Tan Y. Intestinal absorption mechanisms of berberine, palmatine, jateorhizine, and coptisine: involvement of P-glycoprotein. Xenobiotica. 2011 Apr;41(4):290-6. doi: 10.3109/00498254.2010.529180. Epub 2011 Feb 14. PubMed PMID: 21319959. 6: Guo J, Wang SB, Yuan TY, Wu YJ, Yan Y, Li L, Xu XN, Gong LL, Qin HL, Fang LH, Du GH. Coptisine protects rat heart against myocardial ischemia/reperfusion injury by suppressing myocardial apoptosis and inflammation. Atherosclerosis. 2013 Dec;231(2):384-91. doi: 10.1016/j.atherosclerosis.2013.10.003. Epub 2013 Oct 16. PubMed PMID: 24267256. 7: Chen HY, Jin Z, Chen SQ. [Preparation and stuctural behavior of the inclusion complex of beta-cyclodextrin and coptisine hydrochloride]. Zhong Yao Cai. 2012 Jan;35(1):138-41. Chinese. PubMed PMID: 22734425. 8: Li J, Qiu DM, Chen SH, Cao SP, Xia XL. Suppression of human breast cancer cell metastasis by coptisine in vitro. Asian Pac J Cancer Prev. 2014;15(14):5747-51. PubMed PMID: 25081696. 9: Gong LL, Fang LH, Qin HL, Lv Y, Du GH. Analysis of the mechanisms underlying the vasorelaxant action of coptisine in rat aortic rings. Am J Chin Med. 2012;40(2):309-20. PubMed PMID: 22419425. 10: Gong LL, Fang LH, Wang SB, Sun JL, Qin HL, Li XX, Wang SB, Du GH. Coptisine exert cardioprotective effect through anti-oxidative and inhibition of RhoA/Rho kinase pathway on isoproterenol-induced myocardial infarction in rats. Atherosclerosis. 2012 May;222(1):50-8. doi: 10.1016/j.atherosclerosis.2012.01.046. Epub 2012 Feb 6. PubMed PMID: 22387061. 11: Zou ZY, Hu YR, Ma H, Wang YZ, He K, Xia S, Wu H, Xue DF, Li XG, Ye XL. Coptisine attenuates obesity-related inflammation through LPS/TLR-4-mediated signaling pathway in Syrian golden hamsters. Fitoterapia. 2015 Sep;105:139-46. doi: 10.1016/j.fitote.2015.06.005. Epub 2015 Jun 11. PubMed PMID: 26073947. 12: Yu D, Fu S, Cao Z, Bao M, Zhang G, Pan Y, Liu W, Zhou Q. Unraveling the novel anti-osteosarcoma function of coptisine and its mechanisms. Toxicol Lett. 2014 May 2;226(3):328-36. doi: 10.1016/j.toxlet.2014.02.021. Epub 2014 Mar 7. PubMed PMID: 24607417. 13: Friedemann T, Schumacher U, Tao Y, Leung AK, Schröder S. Neuroprotective Activity of Coptisine from Coptis chinensis (Franch). Evid Based Complement Alternat Med. 2015;2015:827308. doi: 10.1155/2015/827308. Epub 2015 Jul 2. PubMed PMID: 26229546; PubMed Central PMCID: PMC4503580. 14: Zhou K, Hu L, Liao W, Yin D, Rui F. Coptisine Prevented IL-β-Induced Expression of Inflammatory Mediators in Chondrocytes. Inflammation. 2016 Aug;39(4):1558-65. doi: 10.1007/s10753-016-0391-6. PubMed PMID: 27294276. 15: Ro JS, Lee SS, Lee KS, Lee MK. Inhibition of type A monoamine oxidase by coptisine in mouse brain. Life Sci. 2001 Dec 28;70(6):639-45. PubMed PMID: 11833714. 16: Colombo ML, Bugatti C, Mossa A, Pescalli N, Piazzoni L, Pezzoni G, Menta E, Spinelli S, Johnson F, Gupta RC, Dasaradhi L. Cytotoxicity evaluation of natural coptisine and synthesis of coptisine from berberine. Farmaco. 2001 May-Jul;56(5-7):403-9. PubMed PMID: 11482767. 17: Kong WJ, Zhao YL, Xiao XH, Li ZL, Jin C, Li HB. Investigation of the anti-fungal activity of coptisine on Candida albicans growth by microcalorimetry combined with principal component analysis. J Appl Microbiol. 2009 Oct;107(4):1072-80. doi: 10.1111/j.1365-2672.2009.04292.x. Epub 2009 Apr 22. PubMed PMID: 19426275. 18: Suzuki H, Tanabe H, Mizukami H, Inoue M. Selective regulation of multidrug resistance protein in vascular smooth muscle cells by the isoquinoline alkaloid coptisine. Biol Pharm Bull. 2010;33(4):677-82. PubMed PMID: 20410605. 19: Wu J, Zhang H, Hu B, Yang L, Wang P, Wang F, Meng X. Coptisine from Coptis chinensis inhibits production of inflammatory mediators in lipopolysaccharide-stimulated RAW 264.7 murine macrophage cells. Eur J Pharmacol. 2016 Jun 5;780:106-14. doi: 10.1016/j.ejphar.2016.03.037. Epub 2016 Mar 24. PubMed PMID: 27018392. 20: Yan R, Wang Y, Shen W, Liu Y, Di X. Comparative pharmacokinetics of dehydroevodiamine and coptisine in rat plasma after oral administration of single herbs and Zuojinwan prescription. Fitoterapia. 2011 Dec;82(8):1152-9. doi: 10.1016/j.fitote.2011.07.012. Epub 2011 Jul 23. PubMed PMID: 21816210.