6-MethoxydihydrosanguinarineCAS# 72401-54-8 |
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| Cas No. | 72401-54-8 | SDF | Download SDF |
| PubChem ID | 14847270 | Appearance | Powder |
| Formula | C21H17NO5 | M.Wt | 363.36 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| SMILES | CN1C(C2=C(C=CC3=C2OCO3)C4=C1C5=CC6=C(C=C5C=C4)OCO6)OC | ||
| Standard InChIKey | MHPDDMNAUJQRSW-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C21H17NO5/c1-22-19-13(4-3-11-7-16-17(8-14(11)19)26-9-25-16)12-5-6-15-20(27-10-24-15)18(12)21(22)23-2/h3-8,21H,9-10H2,1-2H3 | ||
| 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. | ||
| Description | 1. 6-Methoxydihydrosanguinarine may have anti-inflammatory effects via the inhibition of NO and IL-6 expression through the down-regulation of MAP kinase (ERK1/2, p38) phosphorylation in RAW 264.7 cells. 2. 6-Methoxydihydrosanguinarine has antibacterial activity against Methicillin-resistant Staphylococcus aureus (MRSA) strains with minimum inhibitory concentrations (MICs) ranging from1.9 to 3.9 microg/ml. 3. 6-Methoxydihydrosanguinarine shows a dose-dependent effect at 1-10 microM on causing apoptotic cell death in HT29 colon carcinoma cells (IC50 = 5.0+/-0.2 microM). 4. 6-Methoxydihydrosanguinarine shows strong nematocidal activities, however, it is highly cytotoxic; thus, the prospect of its direct application is low. |
| Targets | NO | IL Receptor | ERK | p38MAPK | PARP | Bcl-2/Bax | Caspase | p53 |
6-Methoxydihydrosanguinarine Dilution Calculator
6-Methoxydihydrosanguinarine Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.7521 mL | 13.7605 mL | 27.5209 mL | 55.0418 mL | 68.8023 mL |
| 5 mM | 0.5504 mL | 2.7521 mL | 5.5042 mL | 11.0084 mL | 13.7605 mL |
| 10 mM | 0.2752 mL | 1.376 mL | 2.7521 mL | 5.5042 mL | 6.8802 mL |
| 50 mM | 0.055 mL | 0.2752 mL | 0.5504 mL | 1.1008 mL | 1.376 mL |
| 100 mM | 0.0275 mL | 0.1376 mL | 0.2752 mL | 0.5504 mL | 0.688 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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Apoptosis inducing effects of 6-methoxydihydrosanguinarine in HT29 colon carcinoma cells.[Pubmed:15646800]
Arch Pharm Res. 2004 Dec;27(12):1253-7.
6-Methoxydihydrosanguinarine (6ME), a benzophenanthridine alkaloid derived from the methanol extracts of Hylomecon hylomeconoides, showed a dose-dependent effect at 1-10 microM on causing apoptotic cell death in HT29 colon carcinoma cells (IC50 = 5.0+/-0.2 microM). Treatment of HT-29 cells with 6ME resulted in the formation of internucleosomal DNA fragmentation. Treatment of the cells with 6ME caused activation of caspase-3, -8 and 9 protease and subsequent proteolytic cleavage of poly(ADP-ribose)polymerase. 6ME increased the expression of p53 and Bax and decreased the expression of Bid. These results indicate that p53 and proapoptotic Bcl-2 family proteins might participate in the antiproliferative activity of 6ME in HT29 cells.
Inhibitory effect of isoquinoline alkaloids on movement of second-stage larvae of Toxocara canis.[Pubmed:12499659]
Biol Pharm Bull. 2002 Dec;25(12):1651-4.
To find new anthelmintics against parasites living in host tissues, we used an in vitro assay to screen isoquinoline alkaloids for nematocidal activity on the larva of dog roundworm, Toxocara canis. To evaluate the efficacy of anthelmintics in vitro, Tsuda et al. previously introduced the concept of Relative Mobility (RM) of Toxocara larvae. After improvement of the assay system using image data processing, we generated a new index, RM(50), the concentration at which RM=50%. However, except for pyrantel, the RM(50) of most existing anthelmintics could not be calculated because of low activity. Of the isoquinoline alkaloids tested, emetine, sanguinarine, 6-Methoxydihydrosanguinarine (6-MS), chelerythrine and berberine showed strong nematocidal activities. However, these compounds were highly cytotoxic; thus, the prospect of their direct application is low. We then tested the cytotoxicity (IC(50)) of other isoquinoline alkaloids in HL60 tissue-culture cells. We continued our search for new anthelmintics by examining in detail the relationship between RM(50) and IC(50). We determined that an ideal target compound would exhibit a low RM(50)/IC(50) ratio. Allocryptopine, dehydrocorydaline and papaverine were identified as potentially effective anthelmintics.
Anti-inflammatory effects of Hylomecon hylomeconoides in RAW 264.7 cells.[Pubmed:22957426]
Eur Rev Med Pharmacol Sci. 2012 Jul;16 Suppl 3:121-5.
BACKGROUND AND OBJECTIVES: Papaveraceae serve as a rich source of various alkaloids which have anti-inflammatory effect. MATERIALS AND METHODS: In this study, we investigated the effect of Hylomecon hylomeconoides ethanol extract (HHE) on lipopolysaccharide (LPS)-induced NO and interleukin-6 (IL-6) production in RAW 264.7 cells. RESULTS: HHE inhibited LPS-induced NO and IL-6 production. Moreover, HHE suppressed the phosphorylation of ERK1/2 and p38 in LPS-induced RAW 264.7 in a dose-dependent manner. Furthermore, major constituents, dihydrosanguinarine and 6-Methoxydihydrosanguinarine, of the chloroform-soluble extract were analyzed. CONCLUSIONS: Taken together, the results of this study indicate that the anti-inflammatory effects of HHE may occur via the inhibition of NO and IL-6 expression through the down-regulation of MAP kinase (ERK1/2, p38) phosphorylation in RAW 264.7 cells.
Antibacterial activity of Hylomecon hylomeconoides against methicillin-resistant Staphylococcus aureus.[Pubmed:19578993]
Appl Biochem Biotechnol. 2010 Apr;160(8):2467-74.
Methicillin-resistant Staphylococcus aureus (MRSA) is serious clinical urgent problems worldwide. In the present study, the antibacterial activity of Hylomecon hylomeconoides was investigated. The EtOH extract and its fraction (n-hexane, CH(2)Cl(2), EtOAc, and H(2)O) were investigated against MRSA. The most active extract (CH(2)Cl(2)) led to the isolation of 6-Methoxydihydrosanguinarine (6-MS), 6-acetonylhydrosanguinarine, and dihydrosanguinarine. These compounds were very active against MRSA strains with minimum inhibitory concentrations (MICs) ranging from 1.95 to 250 microg/ml. Our study did however focus on 6-MS as it appeared to be the most active with MICs in the range of 1.9 to 3.9 microg/ml. These results encourage us to think that 6-MS can be used as a natural antibacterial agent.
