Norcantharidin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04637 |
| CAS | 29745-04-8 |
| Molecular Weight | 168.15 |
| Molecular Formula | C8H8O4 |
| Purity | ≥98% |
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Description
It is an antitumor drug and a PP1 and PP2A inhibitor. It is a modified product of the natural antitumor drug cantharidin. It reduces its urinary system toxicity but not its antitumor efficacy after is demethylated. It induces cell apoptosis and acts as an antineoplastic.
Specification
| Synonyms | rel-(3aR,4S,7R,7aS)-Hexahydro-4,7-epoxyisobenzofuran-1,3-dione; (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-epoxyisobenzofuran-1,3-dione; 7-Oxabicyclo[2.2.1]heptane-exo-cis-2,3-dicarboxylic anhydride; Demethylcantharidin; Isocantharidin; NSC 59023; NCTD; 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-, (3aR,4S,7R,7aS)-rel-; 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-, (3aα,4β,7β,7aα)-; 7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride, exo-; exo-7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid anhydride |
| Storage | Store at RT under inert atmosphere |
| IUPAC Name | rel-(1R,2S,6R,7S)-4,10-dioxatricyclo[5.2.1.02,6]decane-3,5-dione |
| Canonical SMILES | C1CC2C3C(C1O2)C(=O)OC3=O |
| InChI | InChI=1S/C8H8O4/c9-7-5-3-1-2-4(11-3)6(5)8(10)12-7/h3-6H,1-2H2/t3-,4+,5-,6+ |
| InChI Key | JAABVEXCGCXWRR-FBXFSONDNA-N |
Properties
| Appearance | White to Off-white Solid |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 362.5°C at 760 mmHg |
| Melting Point | 110-112°C |
| Density | 1.468±0.06 g/cm3 at 20°C 760 Torr |
| Solubility | Soluble in Chloroform (Slightly, Heated), DMSO (Slightly) |
Reference Reading
1. Norcantharidin, derivative of cantharidin, for cancer stem cells
Chen-Hsi Hsieh, K S Clifford Chao, Hui-Fen Liao, Yu-Jen Chen Evid Based Complement Alternat Med . 2013;2013:838651. doi: 10.1155/2013/838651.
Cancer stem cells (CSCs) existing in human cancers have been demonstrated to be a major cause of cancer treatment resistance, invasion, metastasis, and relapse. Self-renewal pathways, Wnt/ β -catenin, Sonic hedgehog (Shh), and the Notch signaling pathway play critical roles in developing CSCs and lead to angiogenesis, migration, invasion, and metastasis. Multidrug resistance (MDR) is an unfavorable factor causing the failure of treatments against cancer cells. The most important and thoroughly studied mechanism involved in MDR is the active efflux of chemotherapeutic agents through membrane drug transporters. There is growing evidence that Norcantharidin (NCTD), a water-soluble synthetic small molecule derivative of naturally occurring cantharidin from the medicinal insect blister beetle (Mylabris phalerata Pallas), is capable of chemoprevention and tumor inhibition. We summarize investigations into the modulation of self-renewal pathways and MDR in CSCs by NCTD. This review may aid in further investigation of using NCTD to develop more effective strategies for cancer treatment to reduce resistance and recurrence.
2. Effect of norcantharidin on the proliferation, apoptosis, and cell cycle of human mesangial cells
Hong Liu, Yunfeng Huang, Ying Li, Zhifeng Gong, Xiaomei Peng, Kun Ye, Qiaoyu Wei Ren Fail . 2017 Nov;39(1):458-464. doi: 10.1080/0886022X.2017.1308257.
Aims:Norcantharidin (NCTD) regulates immune system function and reduces proteinuria. We sought to investigate the effect of NCTD on proliferation, apoptosis and cell cycle of cultured human mesangial cells (HMC) in vitro.Methods:HMC cells were divided into a normal control group, and various concentrations of NCTD group (2.5, 5, 10, 20, or 40 μg/mL). Cell proliferation was determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay, apoptosis was detected by Annexin V/propidium iodide (PI) assays, and morphological analysis was performed by Hoechest 33258 staining. Finally, cell cycle was analyzed by flow cytometry.Results:NCTD dose and time dependently inhibits HMC proliferation significantly (p < .05). Apoptosis dose and time dependently increased after NCTD treatment. Cell-cycle analysis revealed that the number of cells in the G2 phase increased significantly, whereas the fraction of cells in the S phase decreased, especially 24 h after 5 μg/ml NCTD treatment.Conclusion:NCTD inhibits HMC cell proliferation, induces apoptosis, and affects the cell cycle.
3. Norcantharidin analogues: a patent review (2006 - 2010)
Shenlong Tang, Liping Deng Expert Opin Ther Pat . 2011 Nov;21(11):1743-53. doi: 10.1517/13543776.2011.629190.
Introduction:Norcantharidin (7-oxabicyclo [2.2.1] heptane-2,3-dicarboxylic anhydride) is the demethylated form of cantharidin. Norcantharidin not only has strong anticancer activity, but also eliminates most side-effects in the urinary system, does not cause myelosuppression and increases the number of white blood cells. With structural modification, norcantharidin analogues show potential anticancer activities.Areas covered:A comprehensive patent review of norcantharidin analogues from 2006 to 2010 is presented. Protein phosphatase 1, 2A, 2B and 5 inhibitors are described. The review summarizes the new compounds and lays the foundation for seeking more effective anticancer compounds.Expert opinion:Although norcantharidin has improved activity and toxicity, the effects routinely do not satisfy the current clinical need. Exploring better analogues is vital for changing the current situation, but norcantharidin is a good lead compound.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
