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Cycleanine

Names

[ CAS No. ]:
518-94-5

[ Name ]:
Cycleanine

[Synonym ]:
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

Biological Activity

[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.

Chemical & Physical Properties

[ 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

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds