(+)-Isocorynoline

Names

[ CAS No. ]:
475-67-2

[ Name ]:
(+)-Isocorynoline

[Synonym ]:
artabotrin
1,2,10-Trimethoxy-6aa-aporphin-11-ol
d-isocorydine
(6aS)-1,2,10-Trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-ol
6aα-Aporphin-11-ol, 1,2,10-trimethoxy-
luteanin
isocorydine
(S)-5,6,6a,7-Tetrahydro-1,2,10-trimethoxy-6-methyl-4H-dibenzo[de,g]quinolin-11-ol
iso-Corydine
4H-Dibenzo[de,g]quinolin-11-ol, 5,6,6a,7-tetrahydro-1,2,10-trimethoxy-6-methyl-, (6aS)-
LUTEANINE

Biological Activity

[Description]:

Isocorydine is isolated from Dicranostigma leptopodum (Maxim.) Fedde (DLF). Isocorydine combines with Doxorubicin (DOX) has a promising potential to eradicate hepatocellular carcinoma (HCC)[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

[In Vitro]

Isocorydine (0-400 ug/ml; 48 hours) show a significant decrease in the IC50 for ICD and DOX, the CI values are 0.605, 0.644, 0.804, and 0.707 respectively for Huh-7, Hep-G2, SNU-449 and SNU-387[1]. Isocorydine (0-400 ug/ml; 48 hours) abrogates DOX-induced upregulation of mesenchymal markers and the downregulation of epithelial markers in human HCC cell lines[1]. Cell Viability Assay[1] Cell Line: Huh-7, Hep-G2 , SNU-387, SNU-449 cells Concentration: 0-400 ug/ml Incubation Time: 24 hours Result: Had a higher cytotoxicity in HCC cells in comparison to ICD or DOX alone. Western Blot Analysis[1] Cell Line: Huh-7, Hep-G2 , SNU-387, SNU-449 cells Concentration: Incubation Time: 24 hours Result: Downregulated protein levels of Claundin-1 and E-cadherin.

[In Vivo]

Isocorydine (intraperitoneal injection; 0.4 mg/kg; every 2 days for 2 weeks) retards the tumor growth, but the combined treatment of Doxorubicin (DOX) or ICD significantly inhibits tumor growth[1]. Animal Model: Female nude mice[1] Dosage: 0.4 mg/ml Administration: Injected intraperitoneally every 2 days for 2 weeks Result: Combined treatment of isocorydine and DOX showed a promising potential to eradicate HCC.

[References]

[1]. Pan JX, et al. Isocorydine suppresses doxorubicin-induced epithelial-mesenchymal transition via inhibition of ERK signaling pathways in hepatocellular carcinoma. Am J Cancer Res. 2018 Jan 1;8(1):154-164. eCollection 2018.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
506.1±50.0 °C at 760 mmHg

[ Melting Point ]:
216-220ºC(lit.)

[ Molecular Formula ]:
C₂₀H₂₃NO₄

[ Molecular Weight ]:
341.401

[ Flash Point ]:
259.9±30.1 °C

[ Exact Mass ]:
341.162720

[ PSA ]:
51.16000

[ LogP ]:
3.09

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.604

[ Storage condition ]:
-20℃

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CE1057950

CHEMICAL NAME :: 6a-alpha-Aporphin-11-ol, 1,2,10-trimethoxy-

CAS REGISTRY NUMBER :: 475-67-2

BEILSTEIN REFERENCE NO. :: 0094792

LAST UPDATED :: 199612

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C20-H23-N-O4

MOLECULAR WEIGHT :: 341.44

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 10900 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AUPMAF Acta Universitatis Palackianae Olomucensis, Facultatis Medicae. (Statni Pedagogicke Nakladatelstvi, Ostrovni 30, 1 Nove Mesto, 113 01 Prague 1, Czechoslovakia) V.24- 1961- Volume(issue)/page/year: 61,213,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 104 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CTYAD8 Zhongcaoyao. Chinese Traditional and Herbal Medicine. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.11- 1980- Volume(issue)/page/year: 12,402,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 52 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 31,44,1968

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 56 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CTYAD8 Zhongcaoyao. Chinese Traditional and Herbal Medicine. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.11- 1980- Volume(issue)/page/year: 12,402,1981

Safety Information

[ WGK Germany ]:
3

[ RTECS ]:
CE1057950

Precursor & DownStream

Precursor

DownStream

Related Compounds

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