DMP 543Potent, orally active ACh release enhancer CAS# 160588-45-4 |
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Quality Control & MSDS
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| Cas No. | 160588-45-4 | SDF | Download SDF |
| PubChem ID | 9887884 | Appearance | Powder |
| Formula | C26H18F2N2O | M.Wt | 412.44 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble to 100 mM in DMSO and to 50 mM in ethanol | ||
| Chemical Name | 10,10-bis[(2-fluoropyridin-4-yl)methyl]anthracen-9-one | ||
| SMILES | C1=CC=C2C(=C1)C(=O)C3=CC=CC=C3C2(CC4=CC(=NC=C4)F)CC5=CC(=NC=C5)F | ||
| Standard InChIKey | MUJBUUDUXGDXLW-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C26H18F2N2O/c27-23-13-17(9-11-29-23)15-26(16-18-10-12-30-24(28)14-18)21-7-3-1-5-19(21)25(31)20-6-2-4-8-22(20)26/h1-14H,15-16H2 | ||
| 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 | K+ channel blocker and acetylcholine release stimulator. Potently enhances K+-stimulated [3H]-ACh release from rat hippocampal slices (EC50 = 700 nM), and also increases release of dopamine and glutamate (EC50 values are 0.25 and 0.22 μM, respectively). Orally active in vivo; increases ACh levels in rats (with a minimum effective dose of 1 mg/kg) and exerts a long duration of action. More potent than linopirdine both in vitro and in vivo. |
DMP 543 Dilution Calculator
DMP 543 Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.4246 mL | 12.123 mL | 24.246 mL | 48.4919 mL | 60.6149 mL |
| 5 mM | 0.4849 mL | 2.4246 mL | 4.8492 mL | 9.6984 mL | 12.123 mL |
| 10 mM | 0.2425 mL | 1.2123 mL | 2.4246 mL | 4.8492 mL | 6.0615 mL |
| 50 mM | 0.0485 mL | 0.2425 mL | 0.4849 mL | 0.9698 mL | 1.2123 mL |
| 100 mM | 0.0242 mL | 0.1212 mL | 0.2425 mL | 0.4849 mL | 0.6061 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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Efficient pyridinylmethyl functionalization: synthesis of 10, 10-Bis[(2-fluoro-4-pyridinyl)methyl]-9(10H)-anthracenone (DMP 543), an acetylcholine release enhancing agent.[Pubmed:11073571]
J Org Chem. 2000 Nov 17;65(23):7718-22.
2-Fluoro-4-methylpyridine (3) is efficiently functionalized by chlorination, hydrolysis and methanesulfonylation into the novel alkylating agent 7. This mesylate is used for the bisalkylation of anthrone under carefully defined conditions to prepare the cognition enhancer drug candidate 1. This process proceeds in up to 37% overall yield and is adaptable for large scale synthesis.
2-Fluoro-4-pyridinylmethyl analogues of linopirdine as orally active acetylcholine release-enhancing agents with good efficacy and duration of action.[Pubmed:9804701]
J Med Chem. 1998 Nov 5;41(23):4615-22.
In an effort to improve the pharmacokinetic and pharmacodynamic properties of the cognition-enhancer linopirdine (DuP 996), a number of core structure analogues were prepared in which the 4-pyridyl pendant group was systematically replaced with 2-fluoro-4-pyridyl. This strategy resulted in the discovery of several compounds with improved activity in acetylcholine (ACh) release-enhancing assays, in vitro and in vivo. The most effective compound resulting from these studies, 10, 10-bis[(2-fluoro-4-pyridinyl)methyl]-9(10H)-anthracenone (9), is between 10 and 20 times more potent than linopirdine in increasing extracellular hippocampal ACh levels in the rat with a minimum effective dose of 1 mg/kg. In addition to superior potency, 9 possesses an improved pharmacokinetic profile compared to that of linopirdine. The half-life of 9 (2 h) in rats is 4-fold greater than that of linopirdine (0.5 h), and it showed a 6-fold improvement in brain-plasma distribution over linopirdine. On the basis of its pharmacologic, pharmacokinetic, absorption, and distribution properties, 9 (DMP543) has been advanced for clinical evaluation as a potential palliative therapeutic for treatment of Alzheimer's disease.
Two new potent neurotransmitter release enhancers, 10,10-bis(4-pyridinylmethyl)-9(10H)-anthracenone and 10,10-bis(2-fluoro-4-pyridinylmethyl)-9(10H)-anthracenone: comparison to linopirdine.[Pubmed:9580619]
J Pharmacol Exp Ther. 1998 May;285(2):724-30.
Linopirdine (3,3-bis(4-pyridinylmethyl)-1-phenylindolin-2-one, DUP996) is an extensively studied representative of a class of cognition enhancing compounds that increase the evoked release of neurotransmitters. Recent studies suggest that these agents act through the blockade of specific K+ channels. We have recently identified more potent anthracenone analogs of linopirdine: 10,10-bis(4-pyridinylmethyl)-9(10H)-anthracenone (XE991) and 10,10-bis(2-fluoro-4-pyridinylmethyl)-9(10H)-anthracenone (DMP 543). Although linopirdine possesses an EC50 of 4.2 microM for enhancement of [3H]ACh release from rat brain slices, XE991 and DMP 543 have EC50S of 490 and 700 nM, respectively. In addition to greater in vitro potency relative to linopirdine, both compounds show greater in vivo potency and duration of action. Although 5 mg/kg (p.o.) linopirdine does not lead to statistically significant increases in hippocampal extracellular acetylcholine levels, 5 mg/kg (p.o.) XE991 leads to increases (maximal effect > 90% over baseline) which are sustained for 60 min. Moreover, DMP 543 at 1 mg/kg causes more than a 100% increase in acetylcholine levels with the effect lasting more than 3 hr. At doses relevant to their release-enhancing properties, the only overt symptom consistently observed was tremor, possible via a cholinergic mechanism. These results suggest that XE991 and DMP 543 may prove to be superior to linopirdine as Alzheimer's disease therapeutics. In addition, these agents should be useful pharmacological tools for probing the importance of particular ion channels in the control of neurotransmitter release.
