MecambridineCAS# 31098-60-9 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 31098-60-9 | SDF | Download SDF |
| PubChem ID | 161692 | Appearance | Powder |
| Formula | C22H25NO6 | M.Wt | 399.4 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | [(1S)-3,17,18-trimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15,17,19-hexaen-19-yl]methanol | ||
| SMILES | COC1=C(C(=C2CC3C4=C(C5=C(C=C4CCN3CC2=C1)OCO5)OC)CO)OC | ||
| Standard InChIKey | RJZGHQFMKACAHM-INIZCTEOSA-N | ||
| Standard InChI | InChI=1S/C22H25NO6/c1-25-17-7-13-9-23-5-4-12-6-18-21(29-11-28-18)22(27-3)19(12)16(23)8-14(13)15(10-24)20(17)26-2/h6-7,16,24H,4-5,8-11H2,1-3H3/t16-/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
Mecambridine Dilution Calculator
Mecambridine Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.5038 mL | 12.5188 mL | 25.0376 mL | 50.0751 mL | 62.5939 mL |
| 5 mM | 0.5008 mL | 2.5038 mL | 5.0075 mL | 10.015 mL | 12.5188 mL |
| 10 mM | 0.2504 mL | 1.2519 mL | 2.5038 mL | 5.0075 mL | 6.2594 mL |
| 50 mM | 0.0501 mL | 0.2504 mL | 0.5008 mL | 1.0015 mL | 1.2519 mL |
| 100 mM | 0.025 mL | 0.1252 mL | 0.2504 mL | 0.5008 mL | 0.6259 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Mecambridine induces potent cytotoxic effects, autophagic cell death and modulation of the mTOR/PI3K/Akt signaling pathway in HSC-3 oral squamous cell carcinoma cells.[Pubmed:29422960]
Oncol Lett. 2018 Jan;15(1):292-296.
Plant secondary metabolites including alkaloids, demonstrate a complex diversity in their molecular scaffolds and exhibit tremendous pharmacological potential as anti-cancerous therapeutics. The present study aimed to evaluate the anticancer activity of a natural alkaloid, Mecambridine, against human oral squamous cell carcinoma (OSCC). An MTT assay was used to evaluate cytotoxic effects of Mecambridine on HSC-3 oral squamous cell carcinoma cells. Effects of Mecambridine on autophagy-associated proteins were analyzed by western blotting. Effects on reactive oxygen species (ROS) and mitochondrial membrane potential were assessed by flow cytometry. Results indicated that Mecambridine exhibited an IC50 value of 50 microM and exerted its cytotoxic effects in a dose dependent manner on OSCC HSC-3 cells. Furthermore, it was observed that Mecambridine decreases cell viability and induces autophagy in a dose-dependent manner. The underlying mechanism for the induction of autophagy was demonstrated to be associated with ROS-mediated alterations in mitochondrial membrane potential and modulation of the mechanistic target of rapamycin/phosphoinositide 3-kinase/protein kinase B (m-TOR/PI3K/Akt) signaling pathway in HSC-3 at the IC50. In conclusion, the present study suggests that Mecambridine exhibits substantial anticancer activity against OSCC HSC-3 cells by induction of autophagy and modulates the expression of the mTOR/PI3K/Akt signaling cascade which is considered a potential target pathway for anti-cancer agents.
Chemical and antiviral study on alkaloids from Papaver pseudocanescens M. Pop.[Pubmed:22486038]
Z Naturforsch C J Biosci. 2012 Jan-Feb;67(1-2):22-8.
The phytochemical investigation of the aerial parts of Papaver pseudocanescens M. Pop. of Mongolian origin resulted in the isolation and structural elucidation of 8 alkaloids of the isoquinoline and promorphinane type. 8,14-Dihydroamurine, 8,14-dihydroflavinantine, and flavinantine are promorphinanes. Alborine, Mecambridine, and Mecambridine methohydroxide are retroprotoberberines. Amurensinine is an isopavine alkaloid and O-methylarmepavine is a benzylisoquinoline alkaloid. O-Methylarmepavine is a new alkaloid for the genus Papaver. Promorphinane-type alkaloids have been found for the first time in the species. All structures were established by physical and spectral analysis. As a first attempt to describe some of the biological activities of these alkaloids, the antiviral effect was tested against the in vitro replication of several viruses which belong to different taxonomic groups and represent significant human pathogens. Based on the results, the conclusion could be drawn that particular alkaloids from P. pseudocanescens possess selective antiviral effects against the replication of poliovirus 1 and human rhinovirus 14, two viruses from the Enterovirus genus of the Picornaviridae family.
Alkaloids from Turkish samples of Papaver orientale and P. pseudo-orientale.[Pubmed:17402043]
Planta Med. 1981 Nov;43(11):261-71.
The alkaloids obtained from the capsules of five different collections of wild P. orientale and sixteen different collections of wild P. pseudo-orientale have been investigated and the chromosome numbers of some of the samples determined. Oripavine was the major alkaloid obtained from four of the P. orientale collections, two of which had a diploid chromosome number of 28. These four samples contained isothebaine and alpinigenine as minor alkaloids whereas two contained Mecambridine and orientalidine and the other two contained thebaine and salutaridine. The remaining sample of P. orientale contained Mecambridine as the major alkaloid and also some orientalidine. Thirteen of the sixteen samples of P. pseudo-orientale contained isothebaine, Mecambridine and orientalidine as their major alkaloids with thebaine and salutaridine as minor alkaloids. Alpinigenine was detected in three samples. The diploid chromosome number of four of the thirteen samples was determined as 42. Two samples of P. pseudo-orientale contained salutaridine and thebaine as major alkaloids and had a diploid chromosome number of 14 whereas the remaining sample yielded salutaridine as the major alkaloid with isothebaine, Mecambridine and orientalidine as minor alkaloids and a diploid chromosome number of 28.
