3-(Alkylamino)-4h-Pyrido[4,3-E]-1,2,4-Thiadiazine 1,1-Dioxides as Powerful Inhibitors of Insulin Release from Rat Pancreatic B-Cells: A New Class of Potassium Channel Openers?
Pirotte, Bernard; De Tullio, Pascal; Lebrun, Philippeet al.
1993 • In Journal of Medicinal Chemistry, 36 (21), p. 3211-3213
Herchuelz, André; Université Libre de Bruxelles - ULB
Delarge, Jacques; Université de Liège - ULiège > Chimie Pharmaceutique
Language :
English
Title :
3-(Alkylamino)-4h-Pyrido[4,3-E]-1,2,4-Thiadiazine 1,1-Dioxides as Powerful Inhibitors of Insulin Release from Rat Pancreatic B-Cells: A New Class of Potassium Channel Openers?
Publication date :
15 October 1993
Journal title :
Journal of Medicinal Chemistry
ISSN :
0022-2623
eISSN :
1520-4804
Publisher :
American Chemical Society, Washington, United States - District of Columbia
Noma, A. ATP-Regulated K+ Channels in Cardiac Muscle. Nature 1983, 305, 147–148.
Cook, D. L.; Hales, C. N. Intracellular ATP Directly Blocks K+ Channels in Pancreatic B-cells. Nature 1984, 311, 271–273.
Spruce, A. E.; Standen, N. B.; Stanfield, P. Voltage-Dependent ATP-Sensitive Potassium Channels of Skeletal Muscle Membrane. Nature 1985, 316, 736–738.
Standen, N. B.; Quayle, J. M.; Davies, N. W., Brayden, J. E.; Huang, Y.; Nelson, M. T. Hyperpolarizing Vasodilators activate ATP-Sensitive K+ Channels in Arterial Smooth Muscle. Science 1989, 245, 177–180.
Bemardi, H.; Fosset, M.; Lazdunski, M. Characterization, Purification and Affinity Labeling of the Brain [3H] Glibenclamide-Binding Protein, a Putative Neuronal ATP-Regulated K+ Channel. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 9816–9820.
De Weille, J.; Fosset, M.; Epelbaum, J.; Lazdunski, M. Effectors of ATP-Sensitive K+ Channels Inhibit the Regulatory Effects of Somatostatin and GH-Releasing Factor on Growth Hormone Secretion. Biochem. Biophys. Res. Commun. 1992, 187, 1007–1014.
Hamilton, T. C.; Weston, A. H. Cromakalim, Nicorandil and Pinacidil: Novel Drugs which Open Potassium Channels in Smooth Muscle. Gen. Pharmacol. 1989, 20, 1–9.
Edwards, G.; Weston, A. H. Structure-Activity Relationships of K+ Channel Openers. Trends Pharmacol. Sci. 1990, 11, 417–422.
Robertson, D. W.; Steinberg, M. I. Potassium Channel Modulators: Scientific Applications and Therapeutic Promise, J. Med. Chem. 1990, 33, 1529–1541.
Longman, S. D.; Hamilton, T. C. Potassium Channel Activator Drugs: Mechanism of Action, Pharmacological Properties, and Therapeutic Potential. Med. Res. Rev. 1992, 12, 73–148.
Grant, T. L.; Zuzack, J. S. Effects of K+ Channel Blockers and Cromakalim (BRL 34915) on the Mechanical Activity of Guinea Pig Detrusor Smooth Muscle. J. Pharmacol. Exp. Ther. 1991, 259, 1158–1164.
Weston, A. H.; Edwards, G. Recent Progress in Potassium Channel Opener Pharmacology. Biochem. Pharmacol. 1992, 43, 47–54.
Gopalakrishnan, M.; Johnson, D. E.; Janis, R. A.; Triggle, D. J.; Characterization of Binding of the ATP-Sensitive Potassium Channel Ligand, [3H] Glyburide, to Neuronal and Muscle Preparations. J. Pharmacol. Exp. Ther. 1991, 257, 1162–1171.
Newgreen, D. T.; Bray, K. M.; McHarg, A. D.; Weston, A. H., Duty, S.; Brown, B. S.; Kay, P. B.; Edwards, G.; Longmore, J.; Southerton, J. S. The Action of Diazoxide and Minoxidil Sulphate on Rat Blood Vessels: A Comparison with Cromakalim. Br. J. Pharmacol. 1999, 100, 605–613.
Dunne, M. J.; Yule, D. I.; Gallacher, D. V.; Peterson, O. H. Comparative Study of the Effects of Cromakalim (BRL 34915) and Diazoxide on Membrane Potential, [Ca++]i and ATP-Sensitive Potassium Currents in Insulin-Secreting Cells. J. Membr. Biol. 1990, 114, 53–60.
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.
Garrino, M. G.; Plant, T. D.; Henquin, J. C. Effects of Putative Activators of K+ Channels in Mouse Pancreatic β-Cells. Br. J. Pharmacol. 1989, 98, 957–965.
Lebrun, P.; Antoine, M.-H.; Devreux, V.; Hermann, M.; Herchuelz, A., Paradoxical Inhibitory Effect of Cromakalim on 86Rb Outflow from Pancreatic Islets Cells. J. Pharmacol. Exp. Ther. 1990, 255, 948–953.
Ashcroft, F. M. Adenosine 5′-Triphosphate-Sensitive Potassium Channels. Anna. Rev. Neurosci. 1988, 11, 97–118.
Peterson, O. H.; Dunne, M. J. Regulation of K+ Channels Plays a Crucial Role in the Control of Insulin Secretion. Pflügers Arch. 1989, 414, S115–120.
De Weille, J. R. Modulation of ATP Sensitive Potassium Channels. Cardiovasc. Res. 1992, 26, 1017–1020.
Yap, N. T.; Gaines, K. L.; Rajan, A. S.; Berg, M.; Boyd, A. E. Increased Cytosolic Calcium, a Signal for Sulfonylurea-Stimulated Insulin Release from Beta Cells. J. Biol. Chem. 1987, 262, 2608–2612.
Sturgess, N. C.; Ashford, M. L. J.; Cook, D. L.; Hales, C. M. The Sulfonylurea Receptor May Be an ATP-Sensitive Potassium Channel. Lancet 1985, 474–475.
Panten, U.; Burgfeld, J.; Goerke, F.; Rennicke, M.; Schwanstecher, M.; Wallasch, A.; Zünkler, B. J.; Lenzen, S. Control of Insulin Secretion by Sulfonylureas, Meglitinide and Diazoxide in Relation to their Binding to the Sulfonylurea Receptor in Pancreatic Islets. Biochem. Pharmacol. 1989, 38, 1217–1229.
Schmid-Antomarchi, H.; De Weille, J.; Fosset, M.; Lazdunski, M. The Receptor for Antidiabetic Sulfonylureas Controls the Activity of the ATP-Modulated K+ Channel in Insulin-Secreting Cells. J. Biol. Chem. 1987, 262, 15840–15844.
Lebrun, P.; Antoine, M.-H.; Herchuelz, A. Minireview K+ Channel Openers and Insulin Release. Life Sci. 1992, 51, 795–806.
Kaul, C. L.; Talwalker, P. K.; Grewal, R. S. Hyperglycemic, Antihypertensive and Antidiuretic Properties of Go 8288 and its Comparison with Diazoxide. Arch. Int. Pharmacodyn. Ther. 1978, 233, 92–106.
Pratz, J.; Mondot, S.; Montier, F.; Cavero, I. Effects of the K+ Channel Activators, RP52891, Cromakalim and Diazoxide, on the Plasma Insulin Level, Plasma Renin Activity and Blood Pressure in Rats. J. Pharmacol. Exp. Ther. 1991, 258, 216–222.
Lopez, N.; Basabe, J.; Grant, A.; Krees, S.; Terry, M.; Viktora, J.; Wolff, F. AO44: an Improved Hyperglycemic Agent. Metab., Clin. Exp. 1971, 20, 373–383.
Blayac, J. P.; Ribes, G.; Buys, D.; Puech, R.; Loubatières-Mariani, M. M. Effects of a New Benzothiadiazine Derivative, LN 5330, on Insulin Secretion. Arch. Int. Pharmacodyn. Ther. 1981, 253, 154–163.
Petit, P.; Blayac, J. P.; Manteghetti, M.; Loubatières-Mariani, M. M. Comparative Effects of LN 5330 and Diazoxide on Insulin Release and 86Rb+ Permeability in Perifused Rat Islets of Langerhans. Biochem. Pharmacol. 1991, 42, 787–791.
Wollweber, H.; Horstmann, H.; Stoepel, K.; Garthoff, B.; Puls, W.; Krause, H. P.; Thomas, G. Arzneim.-Forsch./Drug Res. 1981, 31, 279–288.
Lebrun, P.; Devreux, V.; Hermann, M.; Herchuelz, A. Pinacidil Inhibits Insulin Release by Increasing K+ outflow from Pancreatic B-Cells. Eur. J. Pharmacol. 1988, 156, 283–286.
Schwanstecher, M.; Brandt, C.; Behrends, S.; Schaupp, U.; Panten, U. Effect of MgATP on Pinacidil-Induced Displacement of Glibenclamide from the Sulfonylurea Receptor in a Pancreatic β-Cell Line and Rat Cerebral Cortex. Br. J. Pharmacol. 1992, 106, 295–301.
Evans, J. M.; Stemp, G. Potassium Channel Activators—Structure Activity Relationships. In Potassium Channels '90. Structure, Modulation and Clinical Exploitation, London, December 1990.
Delarge, J. Ann. Pharm. Fr. 1973, 31, 467–474.
Di Bella, M.; Rinaldi, M.; Fabio, U.; Manicardi, G. Il Farmaco-Ed. Sc. 1973, 28, 411–417.
Antoine, M.-H.; Berkenboom, G.; Fang, Z.-Y.; Fontaine, J.; Herchuelz, A.; Lebrun, P. Mechanical and Ionic Response of Rat Aorta to Diazoxide. Eur. J. Pharmacol. 1992, 216, 299–306.
Lebrun, P.; Fang, Z.-Y.; Antoine, M.-H.; Herchuelz, A.; Hermann, M.; Berkenboom, G.; Fontaine, J. Hypoglycemic Sulfonylureas Antagonize the Effects of Cromakalim and Pinacidil on 86Rb Fluxes and Contractile Activity in Rat Aorta. Pharmacology 1990, 41, 36–48.
Pirotte, B.; Antoine, M.-H.; de Tullio, P.; Hermann, M.; Herchuelz, A.; Delarge, J.; Lebrun, P. BPDZ44: A New and Potent Activator of ATP-Sensitive K+ Channels. Submitted.
