(+)-Isocorydine
Grundinformationen
- CAS
475-67-2- Standard-SMILES
COc1ccc2c(c1O)-c1c(OC)c(OC)cc3c1[C@H](C2)N(C)CC3- InChIKey
QELDJEKNFOQJOY-ZDUSSCGKSA-N- Summenformel
- C20H23NO4
- Durchschnittliche Molmasse
- 341,4 g/mol
- Monoisotopische Masse
- 341,16270821
Überblick
Isocorydine is an aporphine alkaloid.
Namen und Bezeichner
- Bevorzugter Name
- (+)-Isocorydine
- IUPAC
- (6aS)-1,2,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-ol
- Englischer Name
- Isocorydine hydrochloride
- Summenformel
- C20H23NO4
- Molmasse
- 341.4
Namen und Synonyme
Isocorydine475-67-2(+)-IsocorydineArtabotrinLuteaninUzokoridind-IsocorydineL-(+)-IsocorydineS-(+)-IsocorydineLindcarpine, N,O-dimethyl-Aporphin-11-ol, 1,2,10-trimethoxy-(+)-(S)-Isocorydine
Weitere Namen anzeigen
LUTEANINEAids138466Aids-138466lsocorynoline
(S)-(+)-Isocorydine3B5E87JEOX4H-Dibenzo(de,g)quinolin-11-ol, 5,6,6a,7-tetrahydro-1,2,10-trimethoxy-6-methyl-, (S)-DTXSID201023580NSC-32979(6aS)-1,2,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-ol6a-alpha-APORPHIN-11-OL, 1,2,10-TRIMETHOXY-NSC-645316
Datenbank-Bezeichner
- CAS
475-67-2- PubChem CID
- 10143
- DTXSID
DTXSID201023580- ChEMBL
CHEMBL489525- ChEBI
CHEBI:6000- UNII
- 3B5E87JEOX
- Nikkaji
- J5.971D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,6
- Polarare Oberfläche (TPSA)
- 51,2 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 25
- Formalladung
- 0
- Komplexität
- 475
Experimentelle und physikochemische Eigenschaften
SpringerMaterials PropertiesChemical diffusion
Melting Point185 °C
Physical DescriptionSolid
Collision Cross Section181.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 216 · 216-220 °C(lit.)
- Siedepunkt
- 477.03 °C · 477.03°C (rough estimate)
- Dichte
- 1.2064 · 1.2064 (rough estimate)
- Brechungsindex
- 1.5614 · 1.5614 (estimate)
- Löslichkeit
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- Aggregatzustand
- Cryst.
- pka
- 9.41 · 9.41±0.20(Predicted)
- Farbe
- White to off-white
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Toxikologische Informationen
Toxicity Summary
Isocorydine induces G2/M phase arrest by increasing cyclin B1 and p-CDK1 expression levels, which was caused by decreasing the expression and inhibiting the activation of Cdc25C. The phosphorylation levels of Chk1 and Chk2 were increased after ICD treatment. Furthermore, G2/M arrest induced by ICD can be disrupted by Chk1 siRNA but not by Chk2 siRNA. In addition, isocorydine treatment led to a decrease in the percentage of CD133+ PLC/PRF/5 cells. Interestingly, isocorydine treatment dramatically decreased the tumorigenicity of SMMC-7721 and Huh7 cells. (A15211)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Sicherheitsdaten
- wgk
- 3
- RTECS-Nr.
- CE1057950
- Toxizität
- LD50 intraperitoneal in mouse: 104mg/kg
Chemie und Industrie
Pharmakologische Informationen
Cellular LocationsMembrane
Verwendung und Herstellung
Uses(S)-Isocorydine is found in cherimoya.
Anwendungen
BeschreibungIsocorydine is an aporphine alkaloid that has been found in A. squamosa that has vasodilatory and anticancer activities. It reduces the action potential duration and increases the effective refractory period in isolated canine Purkinje fibers when used at a concentration of 30 μM. Isocorydine induces relaxation of norepinephrine-precontracted isolated rabbit aortic strips with an EC50 value of 12.6 μM. It is cytotoxic to A549 lung cancer cells (IC50 = 197.7 μM), as well as Huh7, HepG2, SNU-449, and SNU-387 hepatic cancer cells (IC50s = 161.3, 148, 262.2, and 254.1 μg/ml, respectively). Isocorydine, in combination with doxorubicin, reduces tumor growth in a Huh7 mouse xenograft model.
Verwendensedative, cholinergic
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