518-94-5

518-94-5 structure

Name: Cycleanine
Chemical Name: Cycleanine
CAS Number: 518-94-5
Molecular Formula: C₃₈H₄₂N₂O₆
Molecular Weight: 622.75
Catalog: Biochemical Chinese herbal medicine ingredients
Create Date: 2018-04-21 08:00:00
Modify Date: 2024-01-02 18:57:08
Cycleanine is a potent vascular selective Calcium antagonist. Cycleanine has analgesic, muscle relaxant and anti-inflammatory activities. Cycleanine has potential for anti-ovarian cancer acting through the apoptosis pathway[1][2].

Name	Cycleanine
Synonyms	2-Furanol,tetrahydro-3,4-dipiperonyl tetrahydro-3,4-dipiperonylfuran-2-ol Cubebine (12ar,24ar)-5,6,17,18-tetramethoxy-1,13-dimethyl-2,3,12a,13,14,15,24,24a-octahydro-1h,12h-8,11:20,23-dietheno[1,10]dioxacyclooctadecino[13,12,11-ij:4,3,2-i'j']diisoquinoline 8,11:20,23-Dietheno-1H,12H-[1,10]dioxacyclooctadecino[13,12,11-ij:4,3,2-i'j']diisoquinoline, 2,3,12a,13,14,15,24,24a-octahydro-5,6,17,18-tetramethoxy-1,13-dimethyl-, (12aR,24aR)- 7,11-di-O-methylisochondodendrine Cycleanine 6,7,6',7'-tetramethoxy-2,2'-dimethyl-cycleanane (11R,26R)-4,5,19,20-Tetramethoxy-10,25-dimethyl-2,17-dioxa-10,25-diazaheptacyclo[26.2.2.2.1.1.0.0]hexatriaconta-1(30),3(36),4,6,13,15,18(33),19,21,28,31,34-dodecaene O,O'-dimethyl-isochondrodendrine

Description	Cycleanine is a potent vascular selective Calcium antagonist. Cycleanine has analgesic, muscle relaxant and anti-inflammatory activities. Cycleanine has potential for anti-ovarian cancer acting through the apoptosis pathway[1][2].
Related Catalog	Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Research Areas >> Inflammation/Immunology
Target	L-type calcium channel
In Vitro	Cycleanine inhibits L-type Ca-current (ICaL) of single rat ventricular cardiomyocytes in a voltage- and frequency-dependent manner[1]. Cycleanine shows modestly less potency against human OSE cells (normal) than the cancer cells[2]. Cycleanine (20 μM; 48 hours) exhibits cytotoxicity for Ovcar-8, A2780, Igrov-1, and Ovcar-4 cell lines with IC50s ranging from 7 to 14 μM[2]. Cycleanine (20 μM; 24 hours) results in significant PARP cleavage (a marker of apoptosis)[2]. Cycleanine (20 μM; 48 hours) causes a significant increase of the population of both early and late apoptotic cells[2]. Cell Cytotoxicity Assay[2] Cell Line: Ovcar-8 cells, A2780 cells, Igrov-1 cells, Ovcar-4 cells Concentration: 20 μM Incubation Time: 48 hours Result: Exhibited cytotoxicity for Ovcar-8, A2780, Igrov-1, and Ovcar-4 cell lines with IC50 values of 10 μM, 7.6 μM, 14 μM, 7.2 μM, respectively. Western Blot Analysis[2] Cell Line: Ovcar-8 cells Concentration: 20 μM Incubation Time: 24 hours Result: Induced 1.1-fold increase in PARP-1 cleavage compared with carboplatin. Apoptosis Analysis[2] Cell Line: Ovcar-8 cells Concentration: 20 μM Incubation Time: 48 hours Result: Caused a significant increase of the population of both early and late apoptotic cells. Cell Cycle Analysis[2] Cell Line: Ovcar-8 cells Concentration: 20 μM Incubation Time: 48 hours Result: Increased the percentage of Ovcar-8 cells in subG1.
In Vivo	Cycleanine inhibits the KCl-induced contraction of rabbit aortic rings with an IC50 of 0.8 nM[1].
References	[1]. Martínez JA, et al. Calcium antagonist properties of the bisbenzylisoquinoline alkaloid cycleanine. Fundam Clin Pharmacol. 1998;12(2):182-7. [2]. Uche FI, et al. Cytotoxicity Effects and Apoptosis Induction by Bisbenzylisoquinoline Alkaloids from Triclisia subcordata. Phytother Res. 2016 Sep;30(9):1533-9.

Density	1.2±0.1 g/cm3
Boiling Point	691.6±55.0 °C at 760 mmHg
Molecular Formula	C₃₈H₄₂N₂O₆
Molecular Weight	622.75
Flash Point	169.8±28.7 °C
Exact Mass	622.304260
PSA	61.86000
LogP	3.96
Vapour Pressure	0.0±2.2 mmHg at 25°C
Index of Refraction	1.586

186581-53-3

477-62-3

518-94-5

Literature: Bhakuni,Dewan S.; Jain,Sudha; Chaturvedi,Rekha Tetrahedron, 1987 , vol. 43, # 17 p. 3975 - 3982

Precursor 2
186581-53-3 477-62-3
DownStream 1
524-20-9

518-94-5	30745-31-4
478-63-7	477-62-3
16846-79-0