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Fangchinoline

Names

[ CAS No. ]:
436-77-1

[ Name ]:
Fangchinoline

[Synonym ]:
Berbaman-7-ol, 6,6',12-trimethoxy-2,2'-dimethyl-
Fangquinoline
FF-0018
d,l-Fangchinolin
(S,S)-(+)-tetrandine
12-O-MethylatherosperMoline
(1β)-6,6',12-Trimethoxy-2,2'-dimethylberbaman-7-ol
Tetrandrine B
6,6',12-Trimethoxy-2,2'-dimethylberbaman-7-ol
Hanfangichin B
N1799
I06-1344
THALRUGOSINE
Fangchinoline
7-o-demethyltetrandrine

Biological Activity

[Description]:

Fangchinoline is isolated from Stephania tetrandra with extensive biological activities, such as enhancing immunity, anti-inflammatory sterilization and anti-atherosclerosis. Fangchinoline, a novel HIV-1 inhibitor, inhibits HIV-1 replication by impairing gp160 proteolytic processing[1]. Fangchinoline targets Focal adhesion kinase (FAK) and suppresses FAK-mediated signaling pathway in tumor cells which highly expressed FAK[2]. Fangchinoline induces apoptosis and adaptive autophagy in bladder cancer[3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer
Signaling Pathways >> Anti-infection >> HIV
Research Areas >> Infection
Signaling Pathways >> Protein Tyrosine Kinase/RTK >> FAK
Signaling Pathways >> Autophagy >> Autophagy

[Target]

HIV-1 replication[1]; Focal adhesion kinase (FAK)[2]; apoptosis; autophagy[3]


[In Vitro]

Fangchinoline (2.5-40 µM; 24-96 hours) inhibits both T24 and 5637 cells in dose-dependent manner, the IC50 values of Fangchinoline in T24 cells are 19.0 µM (24 h), 12.0 µM (48 h) and 7.57 µM (72 h), and 11.9 µM (24 h), 9.92 µM (48 h) and 7.13 µM (72 h) in 5637 cells[1]. Fangchinoline (5 µM; 24 hours) induces a significant increase in the LC3-II/LC3-I ratio and a decrease in p62 in both T24 and 5637 cells, and causes a significant increase in the cleavage of caspase-3[1]. Cell Viability Assay[3] Cell Line: T24 and 5637 cells Concentration: 2.5 µM; 5 µM; 10 µM; 20 µM; 30 µM; 40 µM Incubation Time: 24 hours; 48 hours; 96 hours Result: Inhibited both T24 and 5637 cells proliferation. Western Blot Analysis[3] Cell Line: T24 and 5637 cells Concentration: 5 µM Incubation Time: 24 hours Result: Incresed LC3-II/LC3-I ratio and the cleavage of caspase-3.

[References]

[1]. Wan Z, et al. Fangchinoline inhibits human immunodeficiency virus type 1 replication by interfering with gp160 proteolytic processing. PLoS One. 2012;7(6):e39225.

[2]. Guo B, et al. Fangchinoline as a kinase inhibitor targets FAK and suppresses FAK-mediated signaling pathway in A549. J Drug Target. 2015 Apr;23(3):266-74.

[3]. Fan B, et al. Fangchinoline Induces Apoptosis, Autophagy and Energetic Impairment in Bladder Cancer. Cell Physiol Biochem. 2017;43(3):1003-1011.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
709.7±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C37H40N2O6

[ Molecular Weight ]:
608.723

[ Flash Point ]:
383.0±32.9 °C

[ Exact Mass ]:
608.288635

[ PSA ]:
72.86000

[ LogP ]:
3.78

[ Vapour Pressure ]:
0.0±2.3 mmHg at 25°C

[ Index of Refraction ]:
1.602

[ Storage condition ]:
2-8C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DR9280000
CHEMICAL NAME :
Berbaman-7-ol, 2,2'-dimethyl-6,6',12-trimethoxy-, (1-beta)-
CAS REGISTRY NUMBER :
436-77-1
LAST UPDATED :
199709
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C37-H40-N2-O6
MOLECULAR WEIGHT :
608.79

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>50 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CPBTAL Chemical and Pharmaceutical Bulletin. (Japan Pub. Trading Co., USA, 1255 Howard St., San Francisco, CA 94103) V.6- 1958- Volume(issue)/page/year: 24,2413,1976

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds