Corynoline | CAS#18797-79-0 | AChE inhibitor | cytotoxic to cancer cells

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

MedKoo CAT#: 540091

CAS#: 18797-79-0

Description: Corynoline is an AChE inhibitor found in Corydalis. It displays cytotoxicity in various cancer cell lines.

Chemical Structure

Corynoline

CAS# 18797-79-0

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 540091
Name: Corynoline
CAS#: 18797-79-0
Chemical Formula: C21H21NO5
Exact Mass: 367.14
Molecular Weight: 367.400
Elemental Analysis: C, 68.65; H, 5.76; N, 3.81; O, 21.77

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 300
25mg	USD 720
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Corynoline; BT000613; BT 000613; BT-000613; PL002006; PL 002006; PL-002006; FT0688360; FT 0688360; FT-0688360;

IUPAC/Chemical Name: 5b,13-dimethyl-5b,6,7,12b,13,14-hexahydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol

InChi Key: IQUGPRHKZNCHGC-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H21NO5/c1-21-14-3-4-15-19(27-10-24-15)13(14)8-22(2)20(21)12-7-17-16(25-9-26-17)5-11(12)6-18(21)23/h3-5,7,18,20,23H,6,8-10H2,1-2H3

SMILES Code: CC12C(O)CC3=CC4=C(OCO4)C=C3C1N(C)CC5=C2C=CC6=C5OCO6

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

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Product Data:

Product Data

Instruction:

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Biological target:	Corynoline is a reversible and noncompetitive acetylcholinesterase (AChE) inhibitor with an IC50 of 30.6 μM.
In vitro activity:	Treatment of melanoma cells with corynoline results in G2 cell arrest accompanied by reduced cdc2 activation. Furthermore, corynoline triggers apoptosis of melanoma cells, which is associated with increased expression of Bax and cleaved caspase-3. Reference: Phytother Res. 2020 Oct;34(10):2766-2777. https://pubmed.ncbi.nlm.nih.gov/32430958/
In vivo activity:	Therefore, the present study was intended to investigate the effect of Corynoline (COR) on CFA induced rheumatoid arthritis in a rat model. Results suggested that COR causes significant reduction in paw swelling, edema, arthritis score, thymus and spleen indexes and neutrophil infiltration (p < 0.01). Reference: Mol Cell Biochem. 2021 Feb;476(2):831-839. https://pubmed.ncbi.nlm.nih.gov/33174074/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	31.8	86.66

Preparing Stock Solutions

The following data is based on the product molecular weight 367.40 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.

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. Yi C, Li X, Chen S, Liu M, Lu W, Ye X. Natural product corynoline suppresses melanoma cell growth through inducing oxidative stress. Phytother Res. 2020 Oct;34(10):2766-2777. doi: 10.1002/ptr.6719. Epub 2020 May 19. PMID: 32430958. 2. Liu B, Su K, Wang J, Wang J, Xin Z, Li F, Fu Y. Corynoline Exhibits Anti-inflammatory Effects in Lipopolysaccharide (LPS)-Stimulated Human Umbilical Vein Endothelial Cells through Activating Nrf2. Inflammation. 2018 Oct;41(5):1640-1647. doi: 10.1007/s10753-018-0807-6. PMID: 29748730. 3. Weng W, Wang F, He X, Zhou K, Wu X, Wu X. Protective effect of Corynoline on the CFA induced Rheumatoid arthritis via attenuation of oxidative and inflammatory mediators. Mol Cell Biochem. 2021 Feb;476(2):831-839. doi: 10.1007/s11010-020-03948-8. Epub 2020 Nov 10. PMID: 33174074. 4. Wei L, Ren D, Zhao G, Zhao L. Protective effect of corynoline in a murine allergic rhinitis model via inhibition of caspase-1/NF-κB. Arch Pharm (Weinheim). 2021 Feb;354(2):e2000231. doi: 10.1002/ardp.202000231. Epub 2020 Oct 29. PMID: 33124097.
In vitro protocol:	1. Yi C, Li X, Chen S, Liu M, Lu W, Ye X. Natural product corynoline suppresses melanoma cell growth through inducing oxidative stress. Phytother Res. 2020 Oct;34(10):2766-2777. doi: 10.1002/ptr.6719. Epub 2020 May 19. PMID: 32430958. 2. Liu B, Su K, Wang J, Wang J, Xin Z, Li F, Fu Y. Corynoline Exhibits Anti-inflammatory Effects in Lipopolysaccharide (LPS)-Stimulated Human Umbilical Vein Endothelial Cells through Activating Nrf2. Inflammation. 2018 Oct;41(5):1640-1647. doi: 10.1007/s10753-018-0807-6. PMID: 29748730.
In vivo protocol:	1. Weng W, Wang F, He X, Zhou K, Wu X, Wu X. Protective effect of Corynoline on the CFA induced Rheumatoid arthritis via attenuation of oxidative and inflammatory mediators. Mol Cell Biochem. 2021 Feb;476(2):831-839. doi: 10.1007/s11010-020-03948-8. Epub 2020 Nov 10. PMID: 33174074. 2. Wei L, Ren D, Zhao G, Zhao L. Protective effect of corynoline in a murine allergic rhinitis model via inhibition of caspase-1/NF-κB. Arch Pharm (Weinheim). 2021 Feb;354(2):e2000231. doi: 10.1002/ardp.202000231. Epub 2020 Oct 29. PMID: 33124097.

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1: Mao X, Peng Y, Zheng J. In Vitro and In Vivo Characterization of Reactive Intermediates of Corynoline. Drug Metab Dispos. 2015 Oct;43(10):1491-8. doi: 10.1124/dmd.115.065813. Epub 2015 Aug 10. PubMed PMID: 26261285.

2: Yang C, Zhang C, Wang Z, Tang Z, Kuang H, Kong AN. Corynoline Isolated from Corydalis bungeana Turcz. Exhibits Anti-Inflammatory Effects via Modulation of Nfr2 and MAPKs. Molecules. 2016 Jul 27;21(8). pii: E975. doi: 10.3390/molecules21080975. PubMed PMID: 27472313.

3: Liu R, Gu P, Wang L, Cheng M, Wu Y, Zheng L, Liu Y, Ding L. Study on the pharmacokinetic profiles of corynoline and its potential interaction in traditional Chinese medicine formula Shuanghua Baihe tablets in rats by LC-MS/MS. J Pharm Biomed Anal. 2016 Jan 5;117:247-54. doi: 10.1016/j.jpba.2015.09.009. Epub 2015 Sep 10. PubMed PMID: 26386954.

4: Fang ZZ, Zhang YY, Ge GB, Liang SC, Sun DX, Zhu LL, Dong PP, Cao YF, Yang L. Identification of cytochrome P450 (CYP) isoforms involved in the metabolism of corynoline, and assessment of its herb-drug interactions. Phytother Res. 2011 Feb;25(2):256-63. doi: 10.1002/ptr.3255. PubMed PMID: 20641061.

5: Liu R, Zheng L, Cheng M, Wu Y, Gu P, Liu Y, Ma P, Ding L. Simultaneous determination of corynoline and acetylcorynoline in human urine by LC-MS/MS and its application to a urinary excretion study. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Mar 1;1014:83-9. doi: 10.1016/j.jchromb.2016.01.046. Epub 2016 Feb 2. PubMed PMID: 26882127.

6: Huang G, Yang HJ, Li FM. [Preparation and simultaneous determination of corynoline and acetylcorynoline in the herb of Corydalis bungeana]. Zhongguo Zhong Yao Za Zhi. 2003 Apr;28(4):346-9. Chinese. PubMed PMID: 15139147.

7: Yang C, Xiao Y, Wang Z, Wang S, Chen L, Wu L, Liu G. UHPLC-ESI-MS/MS determination and pharmacokinetic study of two alkaloid components in rat plasma after oral administration of the extract of Corydalis bungeana Turcz. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Jun 1;960:59-66. doi: 10.1016/j.jchromb.2014.04.009. Epub 2014 Apr 18. PubMed PMID: 24786221.

8: Dong ZB, Zhang YH, Zhao BJ, Li C, Tian G, Niu B, Qi H, Feng L, Shao JG. Screening for anti-inflammatory components from Corydalis bungeana Turcz. based on macrophage binding combined with HPLC. BMC Complement Altern Med. 2015 Oct 15;15:363. doi: 10.1186/s12906-015-0907-x. PubMed PMID: 26471417; PubMed Central PMCID: PMC4607007.

9: Wei HL, Liu GT. [Protective action of corynoline, acetylcorynoline and protopine against experimental liver injury in mice]. Yao Xue Xue Bao. 1997 May;32(5):331-6. Chinese. PubMed PMID: 11498866.

10: Kim DK. Inhibitory effect of corynoline isolated from the aerial parts of Corydalis incisa on the acetylcholinesterase. Arch Pharm Res. 2002 Dec;25(6):817-9. PubMed PMID: 12510831.

11: Chlebek J, De Simone A, Hošťálková A, Opletal L, Pérez C, Pérez DI, Havlíková L, Cahlíková L, Andrisano V. Application of BACE1 immobilized enzyme reactor for the characterization of multifunctional alkaloids from Corydalis cava (Fumariaceae) as Alzheimer's disease targets. Fitoterapia. 2016 Mar;109:241-7. doi: 10.1016/j.fitote.2016.01.008. Epub 2016 Jan 11. PubMed PMID: 26779945.

12: Kamigauchi M, Noda Y, Nishijo J, Iwasaki K, Tobetto K, In Y, Tomoo K, Ishida T. Cell adhesion inhibitory activity of (d)-corynoline, a hexahydrobenzo[c]phenanthridine-type alkaloid, and its structure-activity relationship, studied by X-ray crystal structure analysis and molecular docking study. Bioorg Med Chem. 2005 Mar 1;13(5):1867-72. PubMed PMID: 15698804.

13: Zeng WG, Liang WZ, Tu GS. Assay of five corynoline-type alkaloids in Corydalis bungeana by reversed-phase high-performance liquid chromatography. J Chromatogr. 1987 Nov 6;408:426-9. PubMed PMID: 3429541.

14: Wu Y, Liu R, Gu P, Cheng M, Zheng L, Liu Y, Ma P, Ding L. Highly sensitive method for simultaneous determination of nine alkaloids of Shuanghua Baihe tablets in human plasma by LC-MS/MS and its application. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Dec 15;1007:81-92. doi: 10.1016/j.jchromb.2015.10.015. Epub 2015 Nov 7. PubMed PMID: 26590879.

15: Liu Y, Song M, Zhu G, Xi X, Li K, Wu C, Huang L. Corynoline attenuates LPS-induced acute lung injury in mice by activating Nrf2. Int Immunopharmacol. 2017 Jul;48:96-101. doi: 10.1016/j.intimp.2017.04.029. Epub 2017 May 6. PubMed PMID: 28486213.

16: Dong ZB, Li C, Shao JG. [Simultaneous determination of seven components in Pudilan Xiaoyan oral liquid by HPLC]. Zhongguo Zhong Yao Za Zhi. 2015 May;40(9):1747-50. Chinese. PubMed PMID: 26323141.

17: Yoon H, Petrone DA, Lautens M. Diastereoselective palladium-catalyzed arylcyanation/heteroarylcyanation of enantioenriched N-allylcarboxamides. Org Lett. 2014 Dec 19;16(24):6420-3. doi: 10.1021/ol503243a. Epub 2014 Dec 2. PubMed PMID: 25443327.

18: Naruto S, Arakawa S, Kaneko H. Conformational analysis of corynoline and its related compounds. Tetrahedron Lett. 1968 Feb;14:1705-9. PubMed PMID: 5640292.

19: Cahlíková L, Hulová L, Hrabinová M, Chlebek J, Hošťálková A, Adamcová M, Šafratová M, Jun D, Opletal L, Ločárek M, Macáková K. Isoquinoline alkaloids as prolyl oligopeptidase inhibitors. Fitoterapia. 2015 Jun;103:192-6. doi: 10.1016/j.fitote.2015.04.004. Epub 2015 Apr 9. PubMed PMID: 25863351.

20: Petrone DA, Yoon H, Weinstabl H, Lautens M. Additive effects in the palladium-catalyzed carboiodination of chiral N-allyl carboxamides. Angew Chem Int Ed Engl. 2014 Jul 21;53(30):7908-12. doi: 10.1002/anie.201404007. Epub 2014 Jun 10. PubMed PMID: 24916024.

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