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Research Article

Quantitative structure-activity relationship study of ATP-sensitive potassium channel openers: Derivatives of 3-alkylamino-4H-1,2,4-benzothiadiazine 1,1-dioxide

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Pages 1-6 | Received 31 Jan 2007, Accepted 09 Apr 2007, Published online: 04 Oct 2008

References

  • Noma A. ATP-regulated K+ channels in cardiac muscle. Nature 1983; 305: 147–148
  • Cook DL, Hales CN. Intracellular ATP directly blocks K+ channels in pancreatic B- cells. Nature 1984; 311: 271–273
  • Bernardi H, Fosset AM, Lazdunski M. Characterization, purification and affinity labeling of the brain[3H]glibendamide-binding protein, a putative neuronal ATP- regulated K+ channel. Proc Natl Acad Sci USA 1988; 85: 9816–9820
  • Standen NB, Quayle JM, Davies NW, Brayden JE, Huang Y, Nelson MT. Hyperpolarizing vasodialaters activate ATP-sensitive K+ channels in arterial smooth muscle. Science 1989; 245: 177–180
  • Allard B, Lazdunski M. Pharmacological properties of ATP-sensitive K+ channels in mammalian skeletal muscle cells. Eur J Pharmacol 1993; 236: 419–426
  • Quayle JM, Nelson MT, Standen NB. ATP sensitive and inwardly rectifying potassium channels in smooth muscle. Physiol Rev 1997; 77: 1165–1232
  • Bryan J, Aguilar-Bryan L. The ABCs of ATP-sensitive potassium channels: More pieces of the puzzle. Curr Opin Cell Biol 1997; 9: 553–559
  • Seino S, Miki T. Physiological and pathophysiological roles of ATP-sensitive K+ channels. Prog Biophys Mol Biol 2003; 81: 133–176
  • Babenko AP, Aguilar-Bryan JA. A view of SUR/Kir6.X KATP channels. Annu Rev Physiol 1998; 60: 667–687
  • D'hahan N, Jacquet H, Moreau C, Catty P, Vivaudou M. A transmembrane domain of the sulfonylurea receptor mediates activation of ATP-sensitive K+ channels by K+ channel openers. Mol Pharmacol 1999; 56: 308–315
  • Seino S. ATP-sensitive potassium channels: A model of heteromultimeric potassium channel/receptor assemblies. Annu Rev Physiol 1999; 61: 337–362
  • Inagaki N, Gonio T, Clement JP. Reconstitution of IKATP: An inward rectifier subunit plus a sulfonylurea receptor. Science 1995; 270: 1166–1170
  • Hambrock A, Löfter-Walz C, Delabar U, Horio Y, Kurachi Y, Quast U. ATP- sensitive K+ channel modulator binding to sulfonylurea receptor SUR2A and SUR2B: Opposite effects of MgADP. Mol Pharmacol 1999; 55: 832–840
  • Petersen OH, Dunne MJ. Regulation of K+ channels plays a crucial role in the control of insulin secretion. Pflueger's Arch 1989; 414: S115–S120
  • Lebrun P. Cationic flux in B-cells from pancreatic islets and pharmacological investigations. Rev Fr Endocrinol Clin Nutr Metab 1993; 34: 241–254
  • Kolb HA. Potassium channels in excitable and non-excitable cells. Rev Physiol Biochem Pharmacol 1990; 15: 51–79
  • Brayden JE. Functional roles of KATP channels in vascular smooth muscles. Clin Exp Pharmacol Physiol 2002; 29: 312–316
  • Seino S, Miki T. Physiological and pathophysiological roles of ATP-sensitive K+ channels. Prog Biophys Mol Biol 2003; 81: 133–176
  • Cotzee WA. ATP-sensitive potassium channels and myocardial ischemia: Why do they open?. Cardiovasc 1992; 6: 201–208
  • Mannhold R. KATP channel openers: Structure-activity relationships and therapeutic potential. Med Res Rev 2004; 24: 213–266
  • Coghlan MJ, Carroll WA, Gopalakrishnan M. Recent development in the biology and medicinal chemistry of potassium channel modulators: Update from a decade progress. J Med Chem 2001; 44: 1627–1653
  • Lebrun P, Devreux V, Hermann M, Herchuelz A. Similarities between the effects of pinacidil and diazoxide on ionic and secretory events in rat pancreatic islets. J Pharmacol Exp Ther 1989; 250: 1011–1018
  • Quast U. Do the K+ channel openers relax smooth muscle by opening K+ channels?. Trends Pharmacol Sci 1993; 14: 332–337
  • Atwal KS. Advances in the structure-activity relationships, mechanism of action, and therapeutic utilities of ATP-sensitive potassium channel openers. Drugs Dev Res 1994; 33: 250–262
  • Gribble FM, Reimann F. Pharmacological modulation of K(ATP) channels. Biochem Soc Trans 2002; 30: 333–339
  • Sebille S, de Tullio P, Boverie S, Antoine M-H, Lebrun P, Pirotte B. Recent development in the chemistry of potassium channel activators: The cromakalim analogues. Curr Med Chem 2004; 11: 1213–1222
  • Manley PW, Quast U. Structure-activity studies of potassium channel opening in pinacidil-types cyanoguanidines, nitroethenediamines, thioureas, and ureas. J Med Chem 1992; 35: 2327–2340
  • Pirotte B, Fontaine J, Lebrun P. Recent advances in the chemistry of potassium channel openers. Curr Med Chem 1995; 2: 537–582
  • Björk E, Berne C, Kämpe O, Wibell P, Oskarsson P, Karlsson FA. Diazoxide treatment at onset preserves residual insulin secretion in adults with autoimmune diabetes. Diabetes 1996; 45: 1427–1430
  • Alemzadeh R, Langley G, Upchurch L, Smith P, Slonim AE. Beneficial effect of diazoxide in obese hyperinsulinemic adults. J Clin Endocrinol Metab 1998; 83: 1911–1915
  • Rasmussen SB, Sorensen TS, Hansen JB, Mandrup-Poulsen T, Hornum L, Markholst H. Functional rest through intensive treatment with insulin and potassium channel openers preserves residual beta-cells function and mass in acutely diabetic BB rats. Horm Metab Res 2000; 32: 294–300
  • Cosgrove K, Antoine M-H, Lee A, Barnes P, de Tullio P, Clayton P, McCloy P, De Lonlay P, Nihoul-Féekéeté C, Robert J, Saudubray J-M, Rahier J, Lindley K, Hussain K, Aynsley-Green A, Pirotte B, Lebrun P, Dunne M. BPDZ 154 activates adenosine 5’-triphosphate-sensitive potassium channels: in vitro studies using rodent insulin-secreting cells and islets isolated from patients with hyperinsulinism. J Clin Endocrinol Metab 2002; 87: 4860–4868
  • Kumar GK, Dastoor FC, Robayo JR, Razzaque MA. Side effects of diazoxide. J Am Med Assoc 1976; 235: 275–276
  • Pirotte B, Antoine M-H, de Tullio P, Hermann M, Herchuelz A, Delange J, Lebrun P. A pyridothiadiazine(BPDZ 44) as a new and potent activator of ATP-sensitive K+ channels. Biochem Pharmacol 1994; 47: 1381–1386
  • Lebrun P, Arkhammar P, Antoine M-H, Nguyen Q-A, Bondo Hansen J, Pirotte B. A potent diazoxide analogue activating ATP-sensitive K+ channels and inhibiting insulin release. Diabetologia 2000; 43: 723–732
  • de Tullio P, Becker B, Boverie S, Dabrowski M, Wahl P, Antoine M-H, Somers F, Sebille S, Ouedraogo R, Bondo Hansen J, Lebrun P, Pirotte P. Toward tissue- selective pancreatic B-cells KATP channel openers belonging to 3-alkylamino-7-halo-4H-1,2,4-benzothiadiazine 1,1-dioxides. J Med Chem 2003; 46: 3342–3353
  • Dabrowski M, Ashcroft FM, Ashfield R, Lebrun P, Pirotte B, Egebjerk J, Hansen JB, Wahl P. The novel diazoxide analog 3-isopropylamino-7-methoxy-4H-1,2,4-benzothiadiazine 1,1-dioxide is a selective Kir6.2/SUR1 channel opener. Diabetes 2002; 51: 1896–1906
  • de Tullio P, Boverie S, Becker B, Antoine M-H, Nguyen Q-A, Francotte P, Counerotte S, Sebille S, Pirotte B, Lebrun P. 3-Alkylamino-4H-1,2,4-benzothiadiazine 1,1-dioxides as ATP-sensitive potassium channel openers: Effect of 6,7-disubstitution on potency and tissue selectivity. J Med Chem 2005; 48: 4990–5000
  • Hansch C, Leo A. Substituents constants for correlation analysis in chemistry and biology. John Wiley, New York 1979
  • ChemDraw Ultra 6.0 and Chem3D Ultra., Cambridge Soft Corporation, Cambridge,USA.
  • Gupta SP, Bhatanagar RP, Singh P, Bindal MC. The relationship of cellular respiration inhibition activity of 7-substituted-4-hydroxyquinoline-3-carboxylic acids with van der Waals volume. Res Commun Chem Pathol Pharmacol 1979; 25: 441–451
  • Wold S. Validation of QSAR's. Quant Struct-Act Relat 1991; 10: 191–193
  • Eriksson L, Jaworska J, Worth AP, Cronin Mark TD, Mc Dowell RM, Gramatica P. Methods for reliability and uncertainty assessment and for applicability evaluation of classification- and regression-based QSARs. Environ Health Persp 2003; 111: 1361–1375

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