Isocorydine
(Synonyms: 异紫堇定碱) 目录号 : GC38414
An aporphine alkaloid with vasodilatory and anticancer activities
Cas No.:475-67-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Isocorydine is an aporphine alkaloid that has been found in A. squamosa that has vasodilatory and anticancer activities.1,2,3,4,5 It reduces the action potential duration and increases the effective refractory period in isolated canine Purkinje fibers when used at a concentration of 30 ?M.2 Isocorydine induces relaxation of norepinephrine-precontracted isolated rabbit aortic strips with an EC50 value of 12.6 ?M.3 It is cytotoxic to A549 lung cancer cells (IC50 = 197.7 ?M), as well as Huh7, HepG2, SNU-449, and SNU-387 hepatic cancer cells (IC50s = 161.3, 148, 262.2, and 254.1 ?g/ml, respectively).4,5 Isocorydine, in combination with doxorubicin, reduces tumor growth in a Huh7 mouse xenograft model.5
1.Bhakuni, D.S., Tewari, S., and Dhar, M.M.Aporphine alkaloids of Annona squamosaPhytochemistry11(5)1819-1822(1972) 2.Zhao, Y.-Q., Li, G.-R., Zhang, D.-Z., et al.Effects of isocorydine on action potentials in isolated canine purkinje fibers and ventricular musclesJ. Mol. Cell. Cardiol.12(4)324-327(1991) 3.Jiang, Q.-S., Huang, X.-N., Sun, A.-S., et al.Relation of vasodilative action of isocorydine to cyclic nucleotidesChi. J. Pharm. Toxicol.15(4)251-255(2011) 4.Zhong, M., Liu, Y., Liu, J., et al.Isocorydine derivatives and their anticancer activitiesMolecules19(8)12099-12115(2014) 5.Pan, J.-X., Chen, G., Li, J.-J., et al.Isocorydine suppresses doxorubicin-induced epithelial-mesenchymal transition via inhibition of ERK signaling pathways in hepatocellular carcinomaAm. J. Cancer Res.8(1)154-164(2018)
| Cas No. | 475-67-2 | SDF | |
| 别名 | 异紫堇定碱 | ||
| Canonical SMILES | COC1=C2C3=C(C=C1OC)CCN(C)[C@@]3([H])CC4=CC=C(OC)C(O)=C24 | ||
| 分子式 | C20H23NO4 | 分子量 | 341.4 |
| 溶解度 | Chloroform: 10 mg/ml | 储存条件 | 4°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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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 |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Isocorydine derivatives and their anticancer activities
Molecules 2014 Aug 12;19(8):12099-115.PMID:25120059DOI:10.3390/molecules190812099.
In order to improve the anticancer activity of Isocorydine (ICD), ten Isocorydine derivatives were prepared through chemical structure modifications, and their in vitro and in vivo activities were experimentally investigated. 8-Amino-isocorydine (8) and 6a,7-dihydrogen-isocorydione (10) could inhibit the growth of human lung (A549), gastric (SGC7901) and liver (HepG2) cancer cell lines in vitro. Isocorydione (2) could inhibit the tumor growth of murine sarcoma S180-bearing mice, and 8-acetamino-isocorydine (11), a pro-drug of 8-amino-isocorydine (8), which is instable in water solution at room temperature, had a good inhibitory effect on murine hepatoma H22-induced tumors. The results suggested that the Isocorydine structural modifications at C-8 could significantly improve the biological activity of this alkaloid, indicating its suitability as a lead compound in the development of an effective anticancer agent.
[Research on anticancer activity of Isocorydine and its derivatives]
Zhongguo Zhong Yao Za Zhi 2017 Aug;42(16):3152-3158.PMID:29171235DOI:10.19540/j.cnki.cjcmm.20170512.008.
Isocorydine and its analogs were extracted from Dicranostigma leptopodum and Stephania yunnanensis through the method of natural products chemistry. Its derivatives were prepared by chemical structure modifications from Isocorydine. MTT method was used to study the inhibitory effect of those compounds on the growth of HepG2, HeLa and MGC-803 cancer cell lines in vitro. The results showed that Isocorydine and its analogs all have the growth inhibition for those cancer cell lines. This paper investigated the structure-activity relationship of Isocorydine and its derivatives with anticancer activity in the aspect of stereochemical structure, functional groups positions of the compounds and the electron density of aromatic rings based on the single crystal diffraction structure and the molecular docking of EGFR and Isocorydine.
The Anti-Sepsis Effect of Isocorydine Screened from Guizhou Ethnic Medicine is Closely Related to Upregulation of Vitamin D Receptor Expression and Inhibition of NFκB p65 Translocation into the Nucleus
J Inflamm Res 2022 Oct 3;15:5649-5664.PMID:36211222DOI:10.2147/JIR.S365191.
Background: The anti-inflammatory application of Guizhou ethnic medicine in the Karst area of China is mainly based on folk medicine experience, and there has been a lack of systematic research, leading to limited application of Guizhou ethnic medicine. Purpose: To evaluate the anti-inflammatory effects of compounds extracted from Guizhou ethnic medicine in the Karst area and investigate their molecular mechanisms. Methods and results: Preliminarily, the anti-inflammatory effects of 181 compounds extracted from Guizhou ethnic medicine were screened in lipopolysaccharide (LPS)-stimulated peritoneal macrophages and the 41 compounds with anti-inflammatory effects were selected. Then, these 41 compounds with anti-inflammatory effects were investigated for their druggability and 18 compounds were selected. Thirdly, compound Hx-150, named Isocorydine, was selected as the candidate compound. In vitro and in vivo, Isocorydine inhibited LPS-induced TNF-α and IL-6 release from LPS-treated mouse peritoneal macrophages. Isocorydine decreased TNF-α, IL-6, and IL-1β levels in the blood, lung, and spleen, and ameliorated lung tissue damage. Mechanistically, Isocorydine had no effect on the mRNA expressions and protein levels of Tlr4, Myd88, and Traf6. Isocorydine also had no effect on the expression of RelA (encoding NFκB p65) mRNA, but inhibited phosphorylation of IκBα and NFκB p65 in the TLR4-mediated signaling pathway. Furthermore, Isocorydine increased the cytoplasmic level of NFκB p65 and decreased its nuclear level in LPS-treated macrophages. Importantly, Isocorydine upregulated Vdr mRNA (encoding the vitamin D receptor) expression and increased the nuclear VDR protein level. Conclusion: Many compounds from Guizhou ethnic medicine had potential anti-inflammatory activities. Among them, Isocorydine has a strong anti-sepsis effect, which is tightly related to its upregulation of VDR expression and inhibition of NFκB p65 translocation into the nucleus, leading to reduced pro-inflammatory cytokines release and protection for LPS-challenged mice.
Isocorydine inhibits cell proliferation in hepatocellular carcinoma cell lines by inducing G2/m cell cycle arrest and apoptosis
PLoS One 2012;7(5):e36808.PMID:22623962DOI:10.1371/journal.pone.0036808.
The treatment of human hepatocellular carcinoma (HCC) cell lines with (+)-isocorydine, which was isolated and purified from Papaveraceae sp. plants, resulted in a growth inhibitory effect caused by the induction of G2/M phase cell cycle arrest and apoptosis. We report that 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. These findings indicate that Isocorydine might be a potential therapeutic drug for the chemotherapeutic treatment of HCC.
Design, synthesis, and anticancer properties of Isocorydine derivatives
Bioorg Med Chem 2017 Dec 15;25(24):6542-6553.PMID:29103873DOI:10.1016/j.bmc.2017.10.027.
Isocorydine (ICD), an aporphine alkaloid, is widely distributed in nature. Its ability to target side population (SP) cells found in human hepatocellular carcinoma (HCC) makes it and its derivative 8-amino-isocorydine (NICD) promising chemotherapeutic agents for the treatment of HCC. To improve the anticancer activity of Isocorydine derivatives, twenty derivatives of NICD were designed and synthesized through chemical structure modifications of the aromatic amino group at C-8. The anti-proliferative activities of all synthesized compounds against human hepatocellular (HepG2), cervical (HeLa), and gastric (MGC-803) cancer cell lines were evaluated using an MTT assay. The results showed that all the synthetic compounds had some tumor cell growth inhibitory activity. The compound COM33 (24) was the most active with IC50 values under 10 μM (IC50 for HepG2 = 7.51 µM; IC50 for HeLa = 6.32 μM). FICD (12) and COM33 (24) were selected for further investigation of their in vitro and in vivo activities due to their relatively good antiproliferative properties. These two compounds significantly downregulated the expression of four key proteins (C-Myc, β-Catenin, CylinD1, and Ki67) in HepG2 cells. The tumor inhibition rate of COM33 (24) in vivo was 73.8% after a dose 100 mg/kg via intraperitoneal injection and the combined inhibition rate of COM33 (24) (50 mg/kg) with sorafenib (50 mg/kg) was 66.5%. The results indicated that these Isocorydine derivatives could potentially be used as targeted chemotherapy agents or could be further developed in combination with conventional chemotherapy drugs to target cancer stem cells (CSCs) and epithelial-to-mesenchymal transition (EMT), the main therapeutic targets in HCC.