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| Targets |
Isocorydine does not have a single defined molecular target. It exhibits multiple pharmacological activities, including vasodilation and anticancer effects. Its vasodilatory activity may involve calcium channel blockade or other mechanisms. Its anticancer activity may involve the induction of apoptosis or inhibition of cell proliferation. The compound's mechanism of action is not fully characterized.
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| ln Vitro |
For Huh-7, Hep-G2, SNU-449, and SNU-387, isocorydine (0-400 ug/ml; 48 hours) significantly reduces the IC50 for both ICD and DOX; the corresponding CI values are 0.605, 0.644, 0.804, and 0.707[1]. In human HCC cell lines, isocorydine (0-400 ug/ml; 48 hours) blocks the overexpression of mesenchymal markers and the downregulation of epithelial markers caused by DOX[1].
Isocorydine exhibits vasodilatory and anticancer activities in vitro. It reduces the action potential duration and increases the effective refractory period. Its anticancer activity has been demonstrated in various cancer cell lines. The compound has also been shown to combine with doxorubicin to eradicate hepatocellular carcinoma. |
| ln Vivo |
While isocorydine (0.4 mg/kg intraperitoneal injection given every two days for two weeks) slows the growth of tumors, the combination of isocorydine and doxorubicin (DOX) treatment greatly slows tumor growth[1].
Isocorydine has vasodilatory activity in vivo. It has been shown to have potential in the treatment of hepatocellular carcinoma, particularly in combination with doxorubicin. Its in vivo anticancer efficacy has been demonstrated in preclinical studies, but specific in vivo data is not detailed in the provided sources. |
| Enzyme Assay |
Isocorydine does not have a standard enzyme/receptor binding assay. Its activity is assessed in cell-based assays that measure its vasodilatory or anticancer effects. For vasodilation, isolated blood vessels are treated with the compound, and the relaxation of the vessels is measured. For anticancer activity, cancer cells are treated with the compound, and cell viability is measured.
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| Cell Assay |
Cell Viability Assay[1]
Cell Types: Huh-7, Hep-G2, SNU-387, SNU-449 cells Tested Concentrations: 0-400 ug/ml Incubation Duration: 24 hrs (hours) Experimental Results: Had a higher cytotoxicity in HCC cells in comparison to ICD or DOX alone. Western Blot Analysis [1] Cell Types: Huh-7, Hep-G2, SNU-387, SNU-449 cells Tested Concentrations: Incubation Duration: 24 hrs (hours) Experimental Results: Downregulated protein levels of Claudin-1 and E-cadherin. In vitro cellular assays for isocorydine involve treating cancer cells with the compound and measuring cell viability or apoptosis. Its vasodilatory activity can be assessed in vascular smooth muscle cells by measuring changes in intracellular calcium levels or by using isolated blood vessels. The compound's ability to enhance the effects of other anticancer agents, such as doxorubicin, can also be studied. |
| Animal Protocol |
Animal/Disease Models: Female nude mice[1]
Doses: 0.4 mg/ml Route of Administration: Injected intraperitoneally every 2 days for 2 weeks Experimental Results: Combined treatment of isocorydine and DOX demonstrated a promising potential to eradicate HCC. In vivo animal experiments for isocorydine would involve administering the compound to animal models of cancer or hypertension. Its efficacy in reducing tumor growth or lowering blood pressure would be assessed. Its combination with other anticancer agents could also be evaluated. However, specific in vivo data is not provided in the sources. |
| ADME/Pharmacokinetics |
Isocorydine has a molecular weight of 341.40 and a molecular formula of C20H23NO4. It is a lipophilic alkaloid that is soluble in organic solvents such as methanol, ethanol, and DMSO. Its pharmacokinetic properties, such as oral bioavailability and half-life, are not specified in the provided sources. The compound is typically used in research applications.
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| Toxicity/Toxicokinetics |
Toxicity Summary
Isopropylamine induced G2/M phase arrest by increasing the expression levels of cyclin B1 and phosphorylated CDK1 (p-CDK1), due to decreased Cdc25C expression and inhibited activation. ICD treatment increased the phosphorylation levels of Chk1 and Chk2. Furthermore, ICD-induced G2/M phase arrest could be blocked by Chk1 siRNA but not by Chk2 siRNA. Additionally, isocilidine treatment led to a decrease in the proportion of CD133+ PLC/PRF/5 cells. Notably, isocilidine treatment significantly reduced the tumorigenicity of SMMC-7721 and Huh7 cells. (A15211) Toxicological data for isocorydine is not detailed in the provided sources. As a naturally occurring alkaloid, its toxicity is likely to be moderate, but specific safety data is not available. The compound is not intended for human use and is supplied for research purposes only. Standard safety precautions should be followed when handling. |
| References | |
| Additional Infomation |
Isocoridine is an apomorphine alkaloid. It has been reported to exist in fern leaves (Pteridophyllum racemosum), Senecio lincangensis, and other organisms with relevant data. (S)-Isocoridine is found in custard apple (cherimoya). (S)-Isocoridine is an alkaloid extracted from Peumus boldus. (S)-Isocoridine belongs to the apomorphine class of alkaloids. Apomorphine alkaloids are a class of quinoline alkaloids containing a dibenzo[de,g]quinoline ring system. See also: Peumus boldus leaves (partial).
Isocorydine is a naturally occurring aporphine alkaloid with vasodilatory and anticancer activities. It is found in various plants, including Argemone mexicana and Berberis densiflora. The compound reduces the action potential duration and increases the effective refractory period. It has been shown to combine with doxorubicin to eradicate hepatocellular carcinoma. Isocorydine is available from various chemical suppliers for research purposes. |
| Molecular Formula |
CHEMICALFORMULAC20H23NO4
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|---|---|
| Molecular Weight |
341.4
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| Exact Mass |
341.162
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| CAS # |
475-67-2
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| PubChem CID |
10143
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
506.1±50.0 °C at 760 mmHg
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| Melting Point |
216-220ºC(lit.)
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| Flash Point |
259.9±30.1 °C
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| Vapour Pressure |
0.0±1.4 mmHg at 25°C
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| Index of Refraction |
1.604
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| LogP |
3.09
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
25
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| Complexity |
475
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=C3C(=C(C=C4)OC)O)OC)OC
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| InChi Key |
QELDJEKNFOQJOY-ZDUSSCGKSA-N
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| InChi Code |
InChI=1S/C20H23NO4/c1-21-8-7-12-10-15(24-3)20(25-4)18-16(12)13(21)9-11-5-6-14(23-2)19(22)17(11)18/h5-6,10,13,22H,7-9H2,1-4H3/t13-/m0/s1
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| Chemical Name |
(6aS)-1,2,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-ol
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| Synonyms |
d-Isocorydine; Luteanin; Isocorydine
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~20 mg/mL (~58.58 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.32 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.32 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. View More
Solubility in Formulation 3: ≥ 2 mg/mL (5.86 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.9291 mL | 14.6456 mL | 29.2912 mL | |
| 5 mM | 0.5858 mL | 2.9291 mL | 5.8582 mL | |
| 10 mM | 0.2929 mL | 1.4646 mL | 2.9291 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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