BMS 191011maxi-K channel opener CAS# 202821-81-6 |
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Quality Control & MSDS
3D structure
Package In Stock
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| Cas No. | 202821-81-6 | SDF | Download SDF |
| PubChem ID | 10474339 | Appearance | Powder |
| Formula | C16H10ClF3N2O3 | M.Wt | 370.71 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | DMSO : 125 mg/mL (337.19 mM; Need ultrasonic) H2O : < 0.1 mg/mL (insoluble) | ||
| Chemical Name | 3-[(5-chloro-2-hydroxyphenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-one | ||
| SMILES | C1=CC(=CC=C1C2=NN(C(=O)O2)CC3=C(C=CC(=C3)Cl)O)C(F)(F)F | ||
| Standard InChIKey | QKOWACXSXTXRKA-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C16H10ClF3N2O3/c17-12-5-6-13(23)10(7-12)8-22-15(24)25-14(21-22)9-1-3-11(4-2-9)16(18,19)20/h1-7,23H,8H2 | ||
| 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 | Potent BKCa channel opener (large-conductance Ca2+-activated potassium channel, KCa1.1). Neuroprotectant in two distinct animal models of stroke (MCAO in the SHR rat and a normotensive model of focal stroke). |
BMS 191011 Dilution Calculator
BMS 191011 Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.6975 mL | 13.4876 mL | 26.9753 mL | 53.9505 mL | 67.4382 mL |
| 5 mM | 0.5395 mL | 2.6975 mL | 5.3951 mL | 10.7901 mL | 13.4876 mL |
| 10 mM | 0.2698 mL | 1.3488 mL | 2.6975 mL | 5.3951 mL | 6.7438 mL |
| 50 mM | 0.054 mL | 0.2698 mL | 0.5395 mL | 1.079 mL | 1.3488 mL |
| 100 mM | 0.027 mL | 0.1349 mL | 0.2698 mL | 0.5395 mL | 0.6744 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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BMS 191011 is a maxi-K channel opener [1].
Maxi-K channels consist of a pore-forming α subunit and a regulatory β subunit. Maxi-K channels are of a high Ca2+ sensitivity [2].
Bath application of BMS-191011 at a concentration of 20 μM strongly reduced the calcium transients. This effect was associated with bursts of bAPs (100 Hz) recorded from Fmr1-/y dendrites without affecting those recorded from wild-type dendrites. This treatment decreased dendritic calcium transients of Fmr1-/y neurons to baseline levels of wild-type neurons [3]. In normoxia, BMS-191011 significantly induced cell death. This effect was indicted by the increases in propidium iodide (PI) uptake by 9.4 ± 2.4 and 16.8 ± 2.1% at 12 and 24 h treatments, respectively. At 12 h and then 24 h, the cellular [ATP] was decreased to 83.4 ± 3.1 and further to 72.3 ± 2.8%. During hypoxia, these effects were increased by ~2-fold in all time points and measurements. PI uptake was increased to 15.1 ± 1.8 at 12 h and then 40.7 ± 1.7% at 24 h. Cellular [ATP] was decreased to 77.8 ± 1.9 at 12 h and then to 43.3 ± 3.4% at 24 h [4].
In male Wistar rats of 8 to 10 weeks old, an i.v. administration with BMS-191011 at 10-100 µg/kg/min increased the retinal arteriol diameter, whereas it did not significantly affect mean arterial pressure and heart rate. Intravitreal injection of iberiotoxin at a dose of 20 pmol/eye significantly attenuated the vasodilator responses of retinal arterioles to BMS-191011 [5]. BMS-191011 demonstrated efficacy as an opener of the cloned large-conductance Ca2+-activated potassium (maxi-K) channel in in vivo stroke models [6].
References:
[1]. Hewawasam P, Ding M, Chen N, et al. Synthesis of water-soluble prodrugs of BMS-191011: a maxi-K channel opener targeted for post-stroke neuroprotection. Bioorganic & medicinal chemistry letters, 2003, 13(10): 1695-1698.
[2]. Valverde MA, Rojas P, Amigo J, et al. Acute activation of Maxi-K channels (hSlo) by estradiol binding to the β subunit. Science, 1999, 285(5435): 1929-1931.
[3]. Zhang Y, Bonnan A, Bony G, et al. Dendritic channelopathies contribute to neocortical and sensory hyperexcitability in Fmr1-/y mice. Nature neuroscience, 2014, 17(12): 1701-1709.
[4]. Gu XQ, Pamenter ME, Siemen D, et al. Mitochondrial but not plasmalemmal BK channels are hypoxia-sensitive in human glioma. Glia, 2014, 62(4): 504-513.
[5]. Mori A, Suzuki S, Sakamoto K, et al. BMS-191011, an opener of large-conductance Ca2+-activated potassium channels, dilates rat retinal arterioles in vivo. Biological and Pharmaceutical Bulletin, 2011, 34(1): 150-152.
[6]. Romine JL, Martin SW, Meanwell NA, et al. 3-[(5-Chloro-2-hydroxyphenyl) methyl]-5-[4-(trifluoromethyl) phenyl]-1, 3, 4-oxadiazol-2 (3 H)-one, BMS-191011: Opener of Large-Conductance Ca2+-Activated Potassium (Maxi-K) Channels, Identification, Solubility, and SAR. Journal of medicinal chemistry, 2007, 50(3): 528-542.
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BMS-191011, an opener of large-conductance Ca2+-activated potassium channels, dilates rat retinal arterioles in vivo.[Pubmed:21212534]
Biol Pharm Bull. 2011;34(1):150-2.
The large-conductance Ca(2+)-activated K(+) (BK(Ca)) channels modulate vascular smooth muscle tone but the role of BK(Ca) channels in regulation of retinal circulation remains unclear. In the present study, we examined the effects of BMS-191011 and NS 1619, openers of BK(Ca) channels, on rat retinal blood vessels in vivo. Male Wistar rats (8- to 10-week-old) were anesthetized with pentobarbital sodium (50 mg/kg, intraperitoneally (i.p.)) and treated with tetrodotoxin (50 microg/kg, intravenously (i.v.)) to eliminate any nerve activity and prevent movement of the eye under artificial ventilation. A mixture solution of adrenaline and noradrenaline (9:1) was infused to maintain adequate systemic circulation. BMS-191011 (10-100 microg/kg, i.v.) and NS 1619 (0.1-1.0 microg/kg, i.v.) increased the diameter of retinal arterioles without altering systemic blood pressure and heart rate significantly. The vasodilator responses to BMS-191011, but not to NS 1619, were significantly diminished by intravitreal injection of iberiotoxin (an inhibitor of BK(Ca) channels, 20 pmol/eye). These results suggest that BMS-191011 dilates rat retinal arterioles through activation of iberiotoxin-sensitive BK(Ca) channels in vivo. The BK(Ca) channel opener could be considered as a candidate for improving retinal circulation without severe cardiovascular side-effects.
3-[(5-Chloro-2-hydroxyphenyl)methyl]-5-[4-(trifluoromethyl)phenyl ]-1,3,4-oxadiazol-2(3H)-one, BMS-191011: opener of large-conductance Ca(2+)-activated potassium (maxi-K) channels, identification, solubility, and SAR.[Pubmed:17266205]
J Med Chem. 2007 Feb 8;50(3):528-42.
Compound 8a (BMS-191011), an opener of the cloned large-conductance, Ca2+-activated potassium (maxi-K) channel, demonstrated efficacy in in vivo stroke models, which led to its nomination as a candidate for clinical evaluation. Its maxi-K channel opening properties were consistent with its structural topology, being derived by combining elements from other known maxi-K openers. However, 8a suffered from poor aqueous solubility, which complicated elucidation of SAR during in vitro evaluation. The activity of 8a in in vivo stroke models and studies directed toward improving its solubility are reported herein. Enhanced solubility was achieved by appending heterocycles to the 8a scaffold, and a notable observation was made that inclusion of a simple amino group (anilines 8k and 8l) yielded excellent in vitro maxi-K ion channel opening activity and enhanced brain-to-plasma partitioning compared to the appended heterocycles.
Synthesis of water-soluble prodrugs of BMS-191011: a maxi-K channel opener targeted for post-stroke neuroprotection.[Pubmed:12729644]
Bioorg Med Chem Lett. 2003 May 19;13(10):1695-8.
A variety of water-soluble prodrugs of BMS-191011 was synthesized and evaluated for solution state stability and rate of conversion to BMS-191011 in rat and human plasma. The deoxycarnitine ester prodrug (11c) was selected for clinical evaluation based on its superior chemical stability, crystallinity and cleavage to BMS-191011 in human plasma.
