N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamideNitroxyl precursor CAS# 142867-52-5 |
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Quality Control & MSDS
3D structure
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| Cas No. | 142867-52-5 | SDF | Download SDF |
| PubChem ID | 688598 | Appearance | Powder |
| Formula | C10H10ClNO5S | M.Wt | 291.71 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble to 100 mM in DMSO | ||
| Chemical Name | [acetyl-(4-chlorophenyl)sulfonylamino] acetate | ||
| SMILES | CC(=O)N(OC(=O)C)S(=O)(=O)C1=CC=C(C=C1)Cl | ||
| Standard InChIKey | GWYBSWWLKXEDLB-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C10H10ClNO5S/c1-7(13)12(17-8(2)14)18(15,16)10-5-3-9(11)4-6-10/h3-6H,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 | A pro-drug of the potent vasorelaxant nitroxyl, H-N=O, which it slowly releases in neutral solution. HNO eventually dimerizes and dehydrates to N2O, without producing NO. Also a powerful inhibitor of aldehyde dehydrogenase. |
N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide Dilution Calculator
N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.4281 mL | 17.1403 mL | 34.2806 mL | 68.5612 mL | 85.7016 mL |
| 5 mM | 0.6856 mL | 3.4281 mL | 6.8561 mL | 13.7122 mL | 17.1403 mL |
| 10 mM | 0.3428 mL | 1.714 mL | 3.4281 mL | 6.8561 mL | 8.5702 mL |
| 50 mM | 0.0686 mL | 0.3428 mL | 0.6856 mL | 1.3712 mL | 1.714 mL |
| 100 mM | 0.0343 mL | 0.1714 mL | 0.3428 mL | 0.6856 mL | 0.857 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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Neuroprotective effects of KR-62980, a new PPARgamma agonist, against chemical ischemia-reperfusion in SK-N-SH cells.[Pubmed:21111719]
Brain Res. 2011 Feb 4;1372:103-14.
PPARgamma agonists exert neuroprotective effects against various types of brain injuries. In the present study, we investigated the effects of KR-62980, a new PPARgamma agonist, and rosiglitazone on the neuronal cell death induced by chemical ischemia-reperfusion in SK-N-SH cells and their underlying molecular mechanisms. Both agonists inhibited chemical ischemia-reperfusion-induced cell death, and the effects were associated with anti-apoptotic action. KR-62980 and rosiglitazone suppressed NO and ROS formation, and N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide, an NO generator, reversed the protective effects of the agonists on cell viability. In the agonist-induced anti-apoptotic process, PTEN expression was suppressed in parallel with increased Akt and ERK phosphorylation, whereas PD98059 (an ERK inhibitor) or wortmannin (a PI-3K inhibitor) abolished the cell survival by KR-62980 and rosiglitazone. All of the effects of KR-62980 and rosiglitazone appeared to be PPARgamma-dependent because the effects were reversed by bisphenol A diglycidyl ether, a PPARgamma antagonist, or by PPARgamma knockdown. Our results demonstrate that two PPARgamma agonists, KR-62980 and rosiglitazone, inhibited chemical ischemia-reperfusion-induced neuronal cell death by PPARgamma-mediated anti-apoptotic and anti-oxidant mechanisms related to PTEN suppression and ERK phosphorylation.
N,O-diacylated-N-hydroxyarylsulfonamides: nitroxyl precursors with potent smooth muscle relaxant properties.[Pubmed:1417812]
Biochem Biophys Res Commun. 1992 Sep 30;187(3):1367-73.
N,O-Diacylated-N-hydroxyarylsulfonamides are capable of slowly releasing nitroxyl (HNO) by simple, non-enzymatic hydrolysis in Krebs solution at 37 degrees C. Release of nitric oxide (NO) was not seen. These compounds were also found to elicit vasorelaxation in rabbit thoracic aorta in vitro, presumably as a result of their ability to release HNO. This effect was enhanced by the addition of superoxide dismutase (SOD). Thus, these results are consistent with previous work indicating that HNO is a potent vasorelaxant.
Prodrugs of nitroxyl as inhibitors of aldehyde dehydrogenase.[Pubmed:1433175]
J Med Chem. 1992 Oct 2;35(20):3648-52.
In the preceding paper, analogs of chlorpropamide with an OMe substituent on the sulfonamide nitrogen were shown to inhibit aldehyde dehydrogenase (AlDH), and it was postulated that these compounds were bioactivated by O-demethylation to release nitroxyl (HN = O, nitrosyl hydride), which is an inhibitor of AlDH. Further evidence for the production of nitroxyl from compounds with O-acyl instead of OMe on the sulfonamide nitrogen is now presented. Thus, nitrous oxide (N2O), the end product of nitroxyl dimerization and disproportionation, was found to be generated on alkaline or enzymatic hydrolysis of N,O-diacylated N-hydroxyarylsulfonamides. Since the latter compounds strongly inhibit yeast AlDH in vitro after bioactivation by an esterase intrinsic to this enzyme, nitroxyl generated from these compounds must be the common intermediate that inhibits AlDH.
