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MedKoo Cat#: 565200 | Name: Epiberberine Chloride
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Description:

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

Epiberberine Chloride is a natural anticancer agent which stabilizes telomeric G4s and inhibits telomerase, specifically recognizing the hybrid-2 telomeric G4 predominant in physiologically relevant K+ solution and converts other telomeric G4 forms to hybrid-2.

Chemical Structure

Epiberberine Chloride
Epiberberine Chloride
CAS#889665-86-5

Theoretical Analysis

MedKoo Cat#: 565200

Name: Epiberberine Chloride

CAS#: 889665-86-5

Chemical Formula: C20H18ClNO4

Exact Mass: 0.0000

Molecular Weight: 371.82

Elemental Analysis: C, 64.61; H, 4.88; Cl, 9.53; N, 3.77; O, 17.21

Price and Availability

Size Price Availability Quantity
5mg USD 290.00 2 weeks
10mg USD 520.00 2 weeks
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Synonym
Epiberberine Chloride
IUPAC/Chemical Name
8,9-Dimethoxy-11,12-dihydro-[1,3]dioxolo[4,5-h]isoquinolino[2,1-b]isoquinolin-13-ium chloride
InChi Key
DGRBIBRPLDAHJH-UHFFFAOYSA-M
InChi Code
InChI=1S/C20H18NO4.ClH/c1-22-18-8-13-5-6-21-10-15-12(3-4-17-20(15)25-11-24-17)7-16(21)14(13)9-19(18)23-2;/h3-4,7-10H,5-6,11H2,1-2H3;1H/q+1;/p-1
SMILES Code
COC1=CC2=C(C3=[N+](CC2)C=C4C(OCO5)=C5C=CC4=C3)C=C1OC.[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
>3 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:
Epiberberine chloride acts as a potent AChE and BChE inhibitor, and a non-competitive BACE1 inhibitor, with IC50s of 1.07, 6.03 and 8.55 μM, respectively.
In vitro activity:
Treatment with epiberberine resulted in a significant reduction in lipid accumulation in a dose-dependent manner in 3T3-L1 adipocytes (Fig. 2b, c). In these experiments, epiberberine (50 μM) inhibited cellular triglyceride accumulation in 3T3-L1 adipocytes by 51 %. Moreover, epiberberine-mediated inhibition of cellular triglyceride accumulation in 3T3-L1 adipocytes occurred in a dose-dependent manner, with an IC50 value of 52.8 μM (Fig. 2b, c). Reference: Arch Pharm Res. 2015 Dec;38(12):2153-62. https://pubmed.ncbi.nlm.nih.gov/26119076/
In vivo activity:
The in vivo anti-metastatic effect of OPB (Epiberberine) was evaluated using a 4 T1 cell xenograft mouse model. Results showed that OPB significantly reversed TGF-β1-triggered morphological changes, expression of EMT biomarkers, and migration, adhesion, and invasion. Furthermore, OPB suppressed TGF-β1-induced Smad2/3 activation, Smad3 phosphorylation and nuclear translocation, and interaction of Smad3 with Smad4. Besides, OPB dramatically decreased the metastatic nodules in the lung without affecting the growth of primary tumors. In conclusion, OPB inhibited TGF-β1-induced EMT possibly by interfering with Smad3. Reference: Toxicol Appl Pharmacol. 2020 Oct 1;404:115179. https://pubmed.ncbi.nlm.nih.gov/32745479/
Solvent mg/mL mM
Solubility
DMSO 25.0 67.24
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 371.82 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. Xiao Y, Deng J, Li C, Gong X, Gui Z, Huang J, Zhang Y, Liu Y, Ye X, Li X. Epiberberine ameliorated diabetic nephropathy by inactivating the angiotensinogen (Agt) to repress TGFβ/Smad2 pathway. Phytomedicine. 2021 Mar;83:153488. doi: 10.1016/j.phymed.2021.153488. Epub 2021 Jan 31. PMID: 33571918. 2. Choi JS, Kim JH, Ali MY, Jung HJ, Min BS, Choi RJ, Kim GD, Jung HA. Anti-adipogenic effect of epiberberine is mediated by regulation of the Raf/MEK1/2/ERK1/2 and AMPKα/Akt pathways. Arch Pharm Res. 2015 Dec;38(12):2153-62. doi: 10.1007/s12272-015-0626-3. Epub 2015 Jun 29. PMID: 26119076. 3. Liu X, Zhang Y, Zhou GJ, Hou Y, Kong Q, Lu JJ, Zhang Q, Chen X. Natural alkaloid 8-oxo-epiberberine inhibited TGF-β1-triggred epithelial-mesenchymal transition by interfering Smad3. Toxicol Appl Pharmacol. 2020 Oct 1;404:115179. doi: 10.1016/j.taap.2020.115179. Epub 2020 Aug 1. PMID: 32745479. 4. Yu M, Ren L, Liang F, Zhang Y, Jiang L, Ma W, Li C, Li X, Ye X. Effect of epiberberine from Coptis chinensis Franch on inhibition of tumor growth in MKN-45 xenograft mice. Phytomedicine. 2020 May 17;76:153216. doi: 10.1016/j.phymed.2020.153216. Epub ahead of print. PMID: 32534357.
In vitro protocol:
1. Xiao Y, Deng J, Li C, Gong X, Gui Z, Huang J, Zhang Y, Liu Y, Ye X, Li X. Epiberberine ameliorated diabetic nephropathy by inactivating the angiotensinogen (Agt) to repress TGFβ/Smad2 pathway. Phytomedicine. 2021 Mar;83:153488. doi: 10.1016/j.phymed.2021.153488. Epub 2021 Jan 31. PMID: 33571918. 2. Choi JS, Kim JH, Ali MY, Jung HJ, Min BS, Choi RJ, Kim GD, Jung HA. Anti-adipogenic effect of epiberberine is mediated by regulation of the Raf/MEK1/2/ERK1/2 and AMPKα/Akt pathways. Arch Pharm Res. 2015 Dec;38(12):2153-62. doi: 10.1007/s12272-015-0626-3. Epub 2015 Jun 29. PMID: 26119076.
In vivo protocol:
1. Liu X, Zhang Y, Zhou GJ, Hou Y, Kong Q, Lu JJ, Zhang Q, Chen X. Natural alkaloid 8-oxo-epiberberine inhibited TGF-β1-triggred epithelial-mesenchymal transition by interfering Smad3. Toxicol Appl Pharmacol. 2020 Oct 1;404:115179. doi: 10.1016/j.taap.2020.115179. Epub 2020 Aug 1. PMID: 32745479. 2. Yu M, Ren L, Liang F, Zhang Y, Jiang L, Ma W, Li C, Li X, Ye X. Effect of epiberberine from Coptis chinensis Franch on inhibition of tumor growth in MKN-45 xenograft mice. Phytomedicine. 2020 May 17;76:153216. doi: 10.1016/j.phymed.2020.153216. Epub ahead of print. PMID: 32534357.
1: Liu L, Li J, He Y. Multifunctional epiberberine mediates multi-therapeutic effects. Fitoterapia. 2020 Nov;147:104771. doi: 10.1016/j.fitote.2020.104771. Epub 2020 Nov 2. PMID: 33152460. 2: Ho HY, Chen MK, Lin CC, Lo YS, Chuang YC, Hsieh MJ. Epiberberine suppresses the metastasis of head and neck squamous cell carcinoma cells by regulating the MMP-13 and JNK pathway. J Cell Mol Med. 2023 Sep 14. doi: 10.1111/jcmm.17954. Epub ahead of print. PMID: 37710409. 3: Zhou LM, Fan JH, Xu MM, Xiong MY, Wang QJ, Chai X, Li XD, Li XG, Ye XL. Epiberberine regulates lipid synthesis through SHP (NR0B2) to improve non- alcoholic steatohepatitis. Biochim Biophys Acta Mol Basis Dis. 2023 Apr;1869(4):166639. doi: 10.1016/j.bbadis.2023.166639. Epub 2023 Jan 11. PMID: 36638873. 4: Zou ZY, Hu YR, Ma H, Feng M, Li XG, Ye XL. Epiberberine reduces serum cholesterol in diet-induced dyslipidemia Syrian golden hamsters via network pathways involving cholesterol metabolism. Eur J Pharmacol. 2016 Mar 5;774:1-9. doi: 10.1016/j.ejphar.2015.11.017. Epub 2015 Dec 1. PMID: 26593426. 5: Lu ZM, Liang JQ, Wang HT, Zhao SH, Zhang H, Tu PF. Total synthesis of epiberberine. J Asian Nat Prod Res. 2012;14(9):873-6. doi: 10.1080/10286020.2012.701621. Epub 2012 Aug 28. PMID: 22924555. 6: Xiao Y, Deng J, Li C, Gong X, Gui Z, Huang J, Zhang Y, Liu Y, Ye X, Li X. Epiberberine ameliorated diabetic nephropathy by inactivating the angiotensinogen (Agt) to repress TGFβ/Smad2 pathway. Phytomedicine. 2021 Mar;83:153488. doi: 10.1016/j.phymed.2021.153488. Epub 2021 Jan 31. PMID: 33571918. 7: Choi JS, Kim JH, Ali MY, Jung HJ, Min BS, Choi RJ, Kim GD, Jung HA. Anti- adipogenic effect of epiberberine is mediated by regulation of the Raf/MEK1/2/ERK1/2 and AMPKα/Akt pathways. Arch Pharm Res. 2015 Dec;38(12):2153-62. doi: 10.1007/s12272-015-0626-3. Epub 2015 Jun 29. PMID: 26119076. 8: Liu X, Zhang Y, Zhou GJ, Hou Y, Kong Q, Lu JJ, Zhang Q, Chen X. Natural alkaloid 8-oxo-epiberberine inhibited TGF-β1-triggred epithelial-mesenchymal transition by interfering Smad3. Toxicol Appl Pharmacol. 2020 Oct 1;404:115179. doi: 10.1016/j.taap.2020.115179. Epub 2020 Aug 1. PMID: 32745479. 9: Wu H, Xie X, Tang Q, Huang T, Tang X, Jiao B, Wang R, Zhu X, Ye X, Ma H, Li X. Epiberberine inhibits Helicobacter pylori and reduces host apoptosis and inflammatory damage by down-regulating urease expression. J Ethnopharmacol. 2024 Jan 10;318(Pt B):117046. doi: 10.1016/j.jep.2023.117046. Epub 2023 Aug 14. PMID: 37586440. 10: Plazas E, Avila M MC, Muñoz DR, Cuca S LE. Natural isoquinoline alkaloids: Pharmacological features and multi-target potential for complex diseases. Pharmacol Res. 2022 Mar;177:106126. doi: 10.1016/j.phrs.2022.106126. Epub 2022 Feb 10. PMID: 35151857. 11: He L, Zhong Z, Chen M, Liang Q, Wang Y, Tan W. Current Advances in Coptidis Rhizoma for Gastrointestinal and Other Cancers. Front Pharmacol. 2022 Jan 3;12:775084. doi: 10.3389/fphar.2021.775084. Erratum in: Front Pharmacol. 2022 May 26;13:931882. PMID: 35046810; PMCID: PMC8762280. 12: Tan L, Li C, Chen H, Mo Z, Zhou J, Liu Y, Ma Z, Xu Y, Yang X, Xie J, Su Z. Epiberberine, a natural protoberberine alkaloid, inhibits urease of Helicobacter pylori and jack bean: Susceptibility and mechanism. Eur J Pharm Sci. 2017 Dec 15;110:77-86. doi: 10.1016/j.ejps.2017.02.004. Epub 2017 Feb 4. PMID: 28167234. 13: Yu M, Ren L, Liang F, Zhang Y, Jiang L, Ma W, Li C, Li X, Ye X. Effect of epiberberine from Coptis chinensis Franch on inhibition of tumor growth in MKN-45 xenograft mice. Phytomedicine. 2020 May 17;76:153216. doi: 10.1016/j.phymed.2020.153216. Epub ahead of print. PMID: 32534357. 14: Yang XY, Ye J, Sun GX, Xue BJ, Zhao YY, Miao PP, Su J, Zhang YJ. [Identification of metabolites of epiberberine in rat liver microsomes and its inhibiting effects on CYP2D6]. Zhongguo Zhong Yao Za Zhi. 2014 Oct;39(19):3855-9. Chinese. PMID: 25612454. 15: Li Y, Wang H, Si N, Ren W, Han L, Xin S, Zuo R, Wei X, Yang J, Zhao H, Bian B. Metabolic profiling analysis of berberine, palmatine, jatrorrhizine, coptisine and epiberberine in zebrafish by ultra-high performance liquid chromatography coupled with LTQ Orbitrap mass spectrometer. Xenobiotica. 2015 Apr;45(4):302-11. doi: 10.3109/00498254.2014.979270. Epub 2014 Nov 5. PMID: 25369727. 16: Lin C, Wu G, Wang K, Onel B, Sakai S, Shao Y, Yang D. Molecular Recognition of the Hybrid-2 Human Telomeric G-Quadruplex by Epiberberine: Insights into Conversion of Telomeric G-Quadruplex Structures. Angew Chem Int Ed Engl. 2018 Aug 20;57(34):10888-10893. doi: 10.1002/anie.201804667. Epub 2018 Jul 18. PMID: 29888501; PMCID: PMC6192034. 17: Lu Q, Li J, Ding P, Mao T, Shi L, Sun Z, Tan X, Jiang H, Dong J, Li Y, Yang X, Shi R. Qingchang Wenzhong Decoction Alleviates DSS-Induced Inflammatory Bowel Disease by Inhibiting M1 Macrophage Polarization In Vitro and In Vivo. Biomed Res Int. 2022 Aug 25;2022:9427076. doi: 10.1155/2022/9427076. PMID: 36060126; PMCID: PMC9436576. 18: Zhang L, Liu H, Shao Y, Lin C, Jia H, Chen G, Yang D, Wang Y. Selective lighting up of epiberberine alkaloid fluorescence by fluorophore-switching aptamer and stoichiometric targeting of human telomeric DNA G-quadruplex multimer. Anal Chem. 2015 Jan 6;87(1):730-7. doi: 10.1021/ac503730j. Epub 2014 Dec 9. PMID: 25429435; PMCID: PMC5515279. 19: Chen N, Yang XY, Guo CE, Bi XN, Chen JH, Chen HY, Li HP, Lin HY, Zhang YJ. The oral bioavailability, excretion and cytochrome P450 inhibition properties of epiberberine: an in vivo and in vitro evaluation. Drug Des Devel Ther. 2017 Dec 28;12:57-65. doi: 10.2147/DDDT.S151660. PMID: 29343943; PMCID: PMC5749554. 20: Wang JL, Fang DC. [Effect of epiberberine on alpha-adrenoceptors]. Yao Xue Xue Bao. 1990;25(4):289-92. Chinese. PMID: 2177949.