Insulin secretagogues, sulfonylurea receptors and KATP channels

Current Pharmaceutical Design

Volumn 11, Issue 21, 2005, Pages 2699-2716

  Bryan, J ^a   Crane, A ^a   Vila Carriles, W H ^a   Babenko, A P ^a   Aguilar Bryan, L ^a  

^a BAYLOR COLLEGE OF MEDICINE   (United States)

Author keywords

Diazoxide; Glibenclamide; Inward rectifier; KATP channel; Potassium channel openers; Repaglinide; Sulfonylurea receptor; Tolbutamide

Indexed keywords

ADENOSINE TRIPHOSPHATE; ANTIDIABETIC AGENT; CALCIUM ION; CHLORIMURON ETHYL; GLIBENCLAMIDE; INSULIN; MEGLITINIDE; POTASSIUM CHANNEL; POTASSIUM ION; RELEASING FACTOR; REPAGLINIDE; SULFONYLUREA DERIVATIVE; SULFONYLUREA RECEPTOR; TOLBUTAMIDE; VOLTAGE GATED CALCIUM CHANNEL;

BINDING AFFINITY; BINDING SITE; CELL MEMBRANE DEPOLARIZATION; CELL MEMBRANE POTENTIAL; CHANNEL GATING; DRUG EFFICACY; DRUG MECHANISM; DRUG RECEPTOR BINDING; DRUG STRUCTURE; ENZYME PHOSPHORYLATION; HYDROGEN BOND; HYPERPOLARIZATION; INSULIN RELEASE; MOLECULAR BIOLOGY; MOLECULAR CLONING; NONHUMAN; PRIORITY JOURNAL; REVIEW; STOICHIOMETRY; STRUCTURE ACTIVITY RELATION;

ANIMALS; ATP-BINDING CASSETTE TRANSPORTERS; BINDING SITES; HUMANS; HYPOGLYCEMIC AGENTS; INSULIN; ION CHANNEL GATING; MODELS, MOLECULAR; POTASSIUM CHANNELS; POTASSIUM CHANNELS, INWARDLY RECTIFYING; RECEPTORS, DRUG; STIMULATION, CHEMICAL; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONYLUREA COMPOUNDS;

EID: 20644464193     PISSN: 13816128     EISSN: None     Source Type: Journal    
DOI: 10.2174/1381612054546879     Document Type: Review

References (199)

1. Aguilar-Bryan L, Bryan J. Molecular biology of adenosine triphosphate-sensitive potassium channels. Endocr Rev 1999; 20: 101-35.
2. Inagaki N, Tsuura Y, Namba N, Masuda K, Gonoi T, Horie M, et al. Cloning and functional characterization of a novel ATP-sensitive potassium channel ubiquitously expressed in rat tissues, including pancreatic islets, pituitary, skeletal muscle, and heart. J Biol Chem 1995; 270: 5691-4.
3. KATP: an inward rectifier subunit plus the sulfonylurea receptor. Science 1995; 270: 1166-70.
4. Zimmet P, Alberti KG, Shaw J. Global and societal implications of the diabetes epidemic. Nature 2001; 414: 782-7.
5. Turner RC. The U.K. Prospective Diabetes Study. A review. Diabetes Care 1998; 21 Suppl 3: C35-8.
6. Unger RH, Madison LL, Amil M. The apparent superiority of tolbutamide over insulin in the regulation of selected clinic patients. South Med J 1958; 51: 1603-10.
7. Best JD, Judzewitsch RG, Pfeifer MA, Beard JC, Halter JB, Porte D, Jr. The effect of chronic sulfonylurea therapy on hepatic glucose production in non-insulin-dependent diabetes. Diabetes 1982; 31: 333-8.
8. Simonson DC, Ferrannini E, Bevilacqua S, Smith D, Barrett E, Carlson R, et al. Mechanism of improvement in glucose metabolism after chronic glyburide therapy. Diabetes 1984; 33: 838-45.
9. Groop L, Luzi L, Melander A, Groop PH, Ratheiser K, Simonson DC, et al. Different effects of glyburide and glipizide on insulin secretion and hepatic glucose production in normal and NIDDM subjects. Diabetes 1987; 36: 1320-8.
10. Group LC. Sulfonylureas in NIDDM. Diabetes Care 1992; 15: 737-54.
11. Groop L, Groop PH, Stenman S, Saloranta C, Totterman KJ, Fyhrquist F, et al. Comparison of pharmacokinetics, metabolic effects and mechanisms of action of glyburide and glipizide during long-term treatment. Diabetes Care 1987; 10: 71-8.
12. Lebovitz HE. In: LeRoith D, Taylor S, Olefsky G, eds.; Diabetes mellitus: A Fundamental and Clinical Text. Lippincot, Williams and Wilkins: Philadelphia 2000; pp. 769-78.
13. DeFronzo RA. Pharmacologic therapy for type 2 diabetes mellitus. Ann Intern Med 1999; 131: 281-303.
14. Loubatieres A. The hypoglycemic sulfonamides: History and developemnt of the problem from 1942 to 1955. Ann N Y Acad Sci 1957; 71: 4-11.
15. Loubatieres A. The discovery of hypoglycemic sulfonamides and particularly of their action mechanism. Acta Diabet Lat 1969; 6: 20-56.
16. Henquin JC. The fiftieth anniversary of hypoglycaemic sulphonamides. How did the mother compound work? Diabetologia 1992; 35: 907-12.
17. Kaubisch N, Hammer R, Wollheim C, Renold AE, Offord RE. Specific receptors for sulfonylureas in brain and in a beta-cell tumor of the rat. Biochem Pharmacol 1982; 31: 1171-4.
18. + channels in cardiac muscle. Nature 1983; 305: 147-8.
19. Trube G, Hescheler J. Inward-rectifying channels in isolated patches of the heart cell membrane: ATP-dependence and comparison with cell-attached patches. Pflugers Arch Eur J Physiol 1984; 401: 178-84.
20. + channels in pancreatic B-cells. Nature 1984; 311: 271-3.
21. Hamill OP, Marty A, Neher E, Sakmann B, Sigworth FJ. Improved patch-clamp techniques for high-resolution current recording from cells and cell-free membrane patches. Pflugers Arch 1981; 391: 85-100.
22. Sturgess NC, Ashford ML, Cook DL, Hales CN. The sulphonylurea receptor may be an ATP-sensitive potassium channel. Lancet 1985; 2: 474-5.
23. Henquin JC. Tolbutamide stimulation and inhibition of insulin release: studies of the underlying ionic mechanisms in isolated rat islets. Diabetologia 1980; 18: 151-60.
24. + fluxes and membrane potential in pancreatic B cells. Biochem Pharmacol 1982; 31: 1407-15.
25. Thorens B. GLUT2 in pancreatic and extra-pancreatic gluco-detection (review). Mol Membr Biol 2001; 18: 265-73.
26. Schuit FC. Is GLUT2 required for glucose sensing? Diabetologia 1997; 40: 104-11.
27. Schuit FC, Huypens P, Heimberg H, Pipeleers DG. Glucose sensing in pancreatic beta-cells: a model for the study of other glucose-regulated cells in gut, pancreas, and hypothalamus. Diabetes 2001; 50: 1-11.
28. Matschinsky FM. Regulation of pancreatic beta-cell glucokinase: from basics to therapeutics. Diabetes 2002; 51 Suppl 3: S394-404.
29. Levin BE. Metabolic sensors: viewing glucosensing neurons from a broader perspective. Physiol Behav 2002; 76: 397-401.
30. + channels that are inhibited by ATP in an insulin-secreting cell line. FEBS Lett 1986; 208: 59-62.
31. + channels in rat pancreatic B-cells is modulated by ADP. FEBS Lett 1986; 208: 63-6.
32. Misler S, Falke LC, Gillis K, McDaniel ML. A metabolite-regulated potassium channel in rat pancreatic B cells. Proc Natl Acad Sci USA 1986; 83: 7119-23.
33. + channel in rat ventricular myocytes. J Membr Biol 1988; 101: 83-92.
34. + channels in isolated membrane patches. J Physiol 1989; 419: 193-211.
35. Hopkins WF, Fatherazi S, Peter-Riesch B, Corkey BE, Cook DL. Two sites for adenine-nucleotide regulation of ATP-sensitive potassium channels in mouse pancreatic beta-cells and HIT cells. J Membr Biol 1992; 129: 287-95.
36. Nichols CG, Shyng SL, Nestorowicz A, Glaser B, Clement IV JP, Gonzalez G, et al. Adenosine diphosphate as an intracellular regulator of insulin secretion. Science 1996; 272: 1785-7.
37. ATP channels. J Biol Chem 2001; 276: 49083-92.
38. Ahren B. Gut peptides and type 2 diabetes mellitus treatment. Curr Diab Rep 2003; 3: 365-72.
39. Drucker DJ. Therapeutic potential of dipeptidyl peptidase IV inhibitors for the treatment of type 2 diabetes. Expert Opin Investig Drugs 2003; 12: 87-100.
40. Vahl T, D'Alessio D. Enteroinsular signaling: perspectives on the role of the gastrointestinal hormones glucagon-like peptide 1 and glucose-dependent insulinotropic polypeptide in normal and abnormal glucose metabolism. Curr Opin Clin Nutr Metab Care 2003; 6: 461-8.
41. Ahren B. Autonomic regulation of islet hormone secretion: Implications for health and disease. Diabetologia 2000; 43: 393-410.
42. Gilon P, Henquin JC. Mechanisms and physiological significance of the cholinergic control of pancreatic beta-cell function. Endocr Rev 2001; 22: 565-604.
43. Nonogaki K. New insights into sympathetic regulation of glucose and fat metabolism. Diabetologia 2000; 43: 533-49.
44. +) permeability. Biochem Pharmacol 1992; 43: 2483-5.
45. + channels in mouse β cells. J Clin Invest 1992; 89: 1288-95.
46. + channels in mouse β cells. J Clin Invest 1993; 91: 871-80.
47. + channel-independent glucose action in rat pancreatic beta-cell. Am J Physiol 1994; 266: C622-7.
48. Aizawa T, Komatsu M, Asanuma N, Sato Y, Sharp GW. Glucose action 'beyond ionic events' in the pancreatic beta cell. TIPS 1998; 19: 496-9.
49. Philipson LH. Beta-cell ion channels: keys to endodermal excitability. Horm Metab Res 1999; 31: 455-61.
50. ATP channels and insulin secretion. Recent Prog Horm Res 2001; 56: 47-68.
51. + channel families regulate insulin secretion. Mol Endocrinol 2001; 15: 1423-35.
52. Thevenod F. Ion channels in secretory granules of the pancreas and their role in exocytosis and release of secretory proteins. Am J Physiol Cell Physiol 2002; 283: C651-72.
53. + channels in pancreatic beta cells: role, regulation and potential as therapeutic targets. Diabetologia 2003; 46: 1046-62.
54. Aguilar-Bryan L, Nichols CG, Wechsler SW, Clement IV JP, Boyd III AE, Gonzalez G, et al. Cloning of the beta cell high-affinity sulfonylurea receptor: a regulator of insulin secretion. Science 1995; 268: 423-6.
55. Aguilar-Bryan L, Nelson DA, Vu QA, Humphrey MB, Boyd III AE. Photoaffinity labeling and partial purification of the beta cell sulfonylurea receptor using a novel, biologically active glyburide analog. J Biol Chem 1990; 265: 8218-24.
56. 3H]glibenclamide. FEBS Lett 1988; 229: 355-9.
57. Dean M, Allikmets R. Complete characterization of the human ABC gene family. J Bioenerg Biomembr 2001; 33: 475-9.
58. Bryan J, Aguilar-Bryan L. In Diabetes Mellitus: A fundamental and clinical text, LeRoith D, Taylor SI, Olefsky JM, eds.; Lippincott-Raven: Philadelphia, 2003.
59. Schwanstecher C, Schwanstecher M. Nucleotide sensitivity of pancreatic ATP-sensitive potassium channels and type 2 diabetes. Diabetes 2002; 51 Suppl 3: S358-62.
60. Huopio H, Otonkoski T, Vauhkonen I, Reimann F, Ashcroft FM, Laakso M, A new subtype of autosoma dominant diabetes attributable to a mutation in the gene for sulfonylurea receptor 1. Lancet 2003; 361: 301-7.
61. Cole SP, Bhardwaj G, Gerlach JH, Mackie JE, Grant CE, Almquist KC, et al. Overexpression of a transporter gene in a multidrug-resistant human lung cancer cell line. Science 1992; 258: 1650-4.
62. IR6.2 peptide. Defining intersubunit gating interactions. J Biol Chem 2002; 277: 43997-4004.
63. Tusnady GE, Bakos E, Varadi A, Sarkadi B. Membrane topology distinguishes a subfamily of the ATP-binding cassette (ABC) transporters. FEBS Lett 1997; 402: 1-3.
64. Raab-Graham KF, Cirilo LJ, Boettcher AA, Radeke CM, Vandenberg CA. Membrane topology of the amino-terminal region of the sulfonylurea receptor. J Biol Chem 1999; 274: 29122-9.
65. Conti I.R, Radeke CM, Shyng SL, Vandenberg CA. Transmembrane topology of the sulfonylurea receptor SUR1. J Biol Chem 2001; 276: 41270-8.
66. Chan KW, Zhang H, Logothetis DE. N-terminal transmembrane domain of the SUR controls trafficking and gating of Kir6 channel subunits. EMBO J 2003; 22: 3833-43.
67. ATP pores define a novel gatekeeper. J Biol Chem 2003; 278: 41577-80,
68. Hopfner KP, Karcher A, Shin DS, Craig L, Arthur LM, Carney JP, et al. Structural biology of Rad50 ATPase: ATP-driven conformational control in DNA double-strand break repair and the ABC-ATPase superfamily. Cell 2000; 101: 789-800.
69. Moody JE, Millen L, Binns D, Hunt JF, Thomas PJ. Cooperative, ATP-dependent association of the nucleotide binding cassettes during the catalytic cycle of ATP-binding cassette transporters. J Biol Chem 2002; 277: 21111-4.
70. Smith PC, Karpowich N, Millen L, Moody JE, Rosen J, Thomas PJ, et al. ATP binding to the motor domain from an ABC transporter drives formation of a nucleotide sandwich dimer. Mol Cell 2002; 10: 139-49.
71. Kerr ID. Structure and association of ATP-binding cassette transporter nucleotide-binding domains. Biochim Biophys Acta 2002; 1561: 47-64.
72. Chen J, Lu G, Lin J, Davidson AL, Quiocho FA. A tweezers-like motion of the ATP-binding cassette dimer in an ABC transport cycle. Mol Cell 2003; 12: 651-61.
73. Janas E, Hofacker M, Chen M, Gompf S, van den Does C, Tampe R. The ATP hydrolysis cycle of the nucleoside-binding domain of the mitochondrial ATP-binding cassette transporter Mdl1p. J Biol Chem 2003; 278: 26862-9.
74. Locher KP, Lee AT, Rees DC. The E. coli BtuCD structure: a framework for ABC transporter architecture and mechanism. Science 2002; 296: 1091-8.
75. Chang G, Roth CB. Structure of MsbA from E. coli: a homolog of the multidrug resistance ATP binding cassette (ABC) transporters. Science 2001; 293: 1793-800.
76. Chang G. Structure of MsbA from Vibrio cholera: a multidrug resistance ABC transporter homolog in a closed conformation. J Mol Biol 2003; 330: 419-30.
77. Stenham DR, Campbell JD, Sansom MS, Higgins CF, Kerr ID, Linton KJ. An atomic detail model for the human ATP binding cassette transporter P-glycoprotein derived from disulphide cross-linking and homology modeling. Faseb J 2003;
78. Shilling RA, Balakrishnan L, Shahi S, Venter H, van Veen HW. A new dimer interface for an ABC transporter. Int J Antimicrob Agents 2003; 22: 200-4.
79. Reuter G, Janvilisri T, Venter H, Shahi S, Balakrishnan L, van Veen HW. The ATP binding cassette multidrug transporter LmrA and lipid transporter MsbA have overlapping substrate specificities. J Biol Chem 2003; 278: 35193-8.
80. Seigneuret M, Garnier-Suillerot A. A structural model for the open conformation of the mdr1 P-glycoprotein based on the MsbA crystal structure. J Biol Chem 2003; 278: 30115-24.
81. + conduction and selectivity. Science 1998; 280: 69-77.
82. Kuo A, Gulbis JM Antcliff JF, Rahman T, Lowe ED, Zimmer J, et al. Crystal structure of the potassium channel KirBac1.1 in the closed state. Science 2003; 300: 1922-6.
83. Nishida M, MacKinnon R. Structural basis of inward rectification: cytoplasmic pore of the G protein-gated inward rectifier GIRK 1 at 1.8 A resolution. Cell 2002; 111: 957-65.
84. ATP channels: function fits form. J Gen Physiol 2003; 122: 471-80.
85. Trapp S, Haiden S, Jones P, Sansom MS, Ashcroft FM. Identification of residues contributing to the ATP binding site of Kir6.2. EMBO J 2003; 22: 2903-12.
86. + channels. Neuron 1996; 16: 10111-7.
87. ATP channels. Diabetes 1996; 45: 1439-45.
88. + channel. J Biol Chem 1996; 271: 24321-4.
89. Thomas PM, Cote GJ, Wohllk N, Haddad B, Mathew PM, Rabl W, et al. Mutations in the sulfonylurea receptor gene in familial persistent hyperinsulinemic hypoglycemia of infancy. Science 1995; 268: 426-9.
90. Ayyagari R, Nestorowicz A, Li Y, Chandrasekharappa S, Chinault C, van Tuinen P, et al. Construction of a YAC contig encompassing the Usher syndrome type 1C and familial hyperinsulinism loci on chromosome 11p14-15.1. Genome Res 1996; 6: 504-14.
91. Inagaki N, Inazawa J, Seino S. cDNA sequence, gene structure, and chromosomal localization of the human ATP-sensitive potassium channel, uKATP-1, gene (KCNJ8). Genomics 1995; 30: 102-4.
92. Isomoto S, Horio Y, Matsumoto S, Kondo C, Yamada M, Gilbert DJ, et al. Sur2 and Kcnj8 genes are tightly linked on the distal region of mouse chromosome 6. Mamm Genome 1997; 8: 790-1.
93. + channel. Journal of Physiology 1997; 499: 715-20.
94. Jahangir A, Terzic A, Shen WK. Potassium channel openers: therapeutic potential in cardiology and medicine. Expert Opin Pharmacother 2001; 2: 1995-2010.
95. Lawson K, Dunre MJ. Peripheral channelopathics as targets for potassium channel openers. Expert Opin Investig Drugs 2001; 10: 1345-59.
96. Chutkow WA, Makielski JC, Nelson DJ, Burant CF, Fan Z. Alternative splicing of Sur2 Exon 17 regulates nucleotide sensitivity of the ATP-sensitive potassium channel. J Biol Chem 1999; 274: 13656-65.
97. ATP channels. Gene 2000; 256: 261-70.
98. Hambrock A, Preisig-Muller R, Russ U, Piehl A, Hanley PJ, Ray J, et al. Pour novel splice variants of sulfonylurea receptor 1. Am J Physiol Cell Physiol 2002; 283: C587-98.
99. ATP channel conferred by a novel splice variant of SUR1. J Physiol 1999; 521 Pt 2: 337-50.
100. Ho K, Nichols CG, Lederer WJ, Lytton J, Vassilev PM, Kanazirska MV, et al. Cloning and expression of an inwardly rectifying ATP-regulated potassium channel. Nature 1993; 362: 31-8.
101. ATP channel. Nature 1994; 370: 456-9.
102. ATP channel [retraction of Ashford ML, Bond CT, Blair TA, Adelman JP. In: Nature 1994 Aug 11;370(6489):456-9]. Nature 1995; 378: 792.
103. Kubo Y, Reuveny F, Slesinger PA, Jan YN, Jan LY. Primary structure and functional expression of a rat G-protein-coupled muscarinic potassium channel. Nature 1993; 364: 802-6.
104. Beech DJ, Zhang H, Nakao K, Bolton TB. K channel activation by nucleotide diphosphates and its inhibition by glibenclamide in vascular smooth muscle cells. British Journal of Pharmacology 1993; 110: 573-82.
105. 4 channels display distinct conductivities but uniform ATP inhibition. J Biol Chem 2000; 275: 31563-6.
106. ATP channels: Functional identity with native channels in the sarcolemma of human ventricular cells. Circ Res 1998; 83: 1132-43.
107. ATP channel-independent regulation of insulin secretion. J Biol Chem 2000; 275: 9270-7.
108. Shiota C, Larsson O, Shelton KD, Shiota M, Efanov AM, Hoy M, et al. Sulfonylurea receptor type 1 knock-out mice have intact feeding-stimulated insulin secretion despite marked impairment in their response to glucose. J Biol Chem 2002; 277: 37176-83.
109. ATP channels enhances insulin-stimulated glucose uptake in skeletal muscle. Proc Natl Acad Sci USA 2001; 98: 11760-4.
110. ATP channels. J Clin Invest 2002; 110: 203-8.
111. ATP channel-deficient mice. Proc Natl Acad Sci USA 1998; 95: 10402-6.
112. + channels in the hypothalamus are essential for the maintenance of glucose homeostasis. Nat Neurosci 2001; 4: 507-12.
113. Miki T, Suzuki M, Shibasaki T, Uemura H, Sato T, Yamaguchi K, et al. Mouse model of Prinzmetal angina by disruption of the inward rectifier Kir6.1. Nat Med 2002; 8: 466-72.
114. ATP channel subunits. Neuron 1997; 18: 827-38.
115. ATP channel complex. J Gen Physiol 1997; 110: 655-64.
116. + channel. FEBS Lett 1997; 409: 232-6.
117. ATP channels. Physiol Rev 1998; 78: 227-45.
118. Deutsch C. Potassium channel ontogeny. Annu Rev Physiol 2002; 64: 19-46.
119. ATP channels. Neuron 1999; 22: 537-48.
120. + channel with an ABC transporter. Neuron 2000; 26: 155-67.
121. Conti LR, Radeke CM, Vandenberg CA. Membrane targeting of ATP-sensitive potassium channel. Effects of glycosylation on surface expression. J Biol Chem 2002; 277: 25416-22.
122. ATP channels. J Biol Chem 1999; 274: 20628-32.
123. ATP channels caused by a sulfonylurea receptor 1 mutation associated with persistent hyperinsulinemic hypoglycemia of infancy. Proc Natl Acad Sci USA 2001; 98: 2882-7.
124. ATP channels. J Biol Chem 2002; 277: 17139-46.
125. ATP Channel Subunits. J Biol Chem 2003; (submitted):
126. Lukacs GL, Mohamed A, Kartner N, Chang XB, Riordan JR, Grinstein S. Conformational maturation of CFTR but not its mutant counterpart (delta F508) occurs in the endoplasmic reticulum and requires ATP. EMBO J 1994; 13: 6076-86.
127. Ward CL, Kopito RR. Intracellular turnover of cystic fibrosis transmembrane conductance regulator. Inefficient processing and rapid degradation of wild-type and mutant proteins. J Biol Chem 1994; 269: 25710-8.
128. + channels in the absence of the sulphonylurea receptor. Nature 1997; 387: 179-83.
129. ATP channel inhibition by ATP requires distinct functional domains of the cytoplasmic C terminus of the pore-forming subunit. Proc Natl Acad Sci USA 1998; 95: 13953-8.
130. ATP channels. FEBS Letters 1999; 445: 131-6.
131. + channel assembly. Biophys J 1999; 76: 2004-17.
132. Giblin JP, Leaney JL, Tinker A. The molecular assembly of ATP-sensitive potassium channels. Determinants on the pore forming subunit. J Biol Chem 1999; 274: 22652-9.
133. ATP channel. Biochem Soc Trans 2002; 30: 323-7.
134. Momose T, Shogi TV, Iwasaki M. Yakugakuzasshi 1961; 81: 1045.
135. Beregi LG. In Gliclazide: Royal Society of Medicine International Congress and Symposium Series; Academic Press, Inc. & Royal Society of Medicine: London, 1980; Vol 20: pp. 5-8.
136. Loubatieres A, Mariani MM, Alric R, Capal J, Ribes G, de Malbosc H. [A new particularly active hypoglycemic sulfonamide, HB 419 (glibenclamide). Diabete 1968; Suppl: 79-86.
137. Loubatieres A, Mariani MM, Ribes G, de Malbosc H, Chapal J. Experimental study of a new especially active hypoglycemic sulfonamide, HB-419 or Glibenclamide. Diabetologia 1969; 5: 1-10.
138. Weber H, Aumuller W, Muth K, Weyer R, Heerdt R, Fauland E, et al. Acylaminoalkylbenzolsulfonylureas. Arzneimittelforschung 1969; 19: Suppl:1326-46.
139. Gutsche K, Schroder E, Rufer C, Loge O. New hypoglycemic benzenesulfonamido-pyrimidines N-substituted 4- N-(2-pyrimidinyl) sulfonyl-phenylacetamides. Arzneimittelforschung 1974; 24: 1028-39.
140. Rufer C, Biere H, Ahrens H, Loge O, Schroder E. Blood glucose lowering sulfonamides with asymmetric carbon atoms. J Med Chem 1974; 17: 708-15.
141. Biere H, Rufer C, Ahrens H, Loge O, Schroder E. Blood glucose lowering sulfonamides with asymmetric carbon atoms. J Med Chem 1974; 17: 716-21.
142. Rufer C, Losert W. Blood glucose lowering sulfonamides with asymmetric carbon atoms. 3. Related N-substituted carbamoylbenzoic acids. J Med Chem 1979; 22: 750-2.
143. Efendic S, Enzmann F, Gutniak M, Nylen A, Zoltobrocki M. Insulin, glucagon and somatostatin in the perfused rat pancreas and the effects of HB 699 (4-(2-(5-chloro-2-metoxy-benzamido)-ethyl)-benzoic acid). Acta Endocrinol (Copenh) 1981; 98: 573-9.
144. Glatt M, Schatz H. The influence off an acyl-amino-alcyl-benzoic acid (HB 699) on biosynthesis and secretion of insulin in isolated rat islets of Langerhans. Diabete Metab 1981; 7: 105-8.
145. Ribes G, Trimble ER, Blayac JP, Wollheim CB, Puech R, Loubatieres-Mariani MM. Effect of a new hypoglycaemic agent (HB 699) on the in vivo secretion of pancreatic hormones in the dog. Diabetologia 1981; 20: 501-5.
146. Kamp F, Kizilbash N, Corkey BE, Berggren PO, Hamilton JA. Sulfonylureas rapidly cross phospholipid bilayer membranes by a free-diffusion mechanism. Diabetes 2003; 52: 2526-31.
147. Kamp F, Hamilton JA. pH gradients across phospholipid membranes caused by fast flip-flop of un-ionized fatty acids. Proc Natl Acad Sci USA 1992; 89: 11367-70.
148. Brown GR, Foubister AJ. Receptor binding sites of hypoglycemic sulfonylureas and related [(acylamino)alkyl]benzoic acids. J Med Chem 1984; 27: 79-81.
149. Grell W, Hurnaus R, Griss G, Sauter R, Rupprecht E, Mark M, et al. Repaglinide and related hypoglycemic benzoic acid derivatives. J Med Chem 1998; 41: 5219-46.
150. Meyer M, Chudziak F, Schwanstecher C, Schwanstecher M, Panten U. Structural requirements of sulphonylureas and analogues for interaction with sulphonylurea receptor subtypes. Br J Pharmacol 1999; 128: 27-34.
151. Garrino MG, Schmeer W, Nenquin M, Meissner HP, Henquin JC. Mechanism of the stimulation of insulin release in vitro by HB 699, a benzoic acid derivative similar to the non-sulphonylurea moiety of glibenclamide. Diabetologia 1985; 28: 697-703.
152. Henquin JC, Garrino MG, Nenquin M. Stimulation of insulin release by benzoic acid derivatives related to the non-sulphonylurea moiety of glibenclamide: structural requirements and cellular mechanisms. Eur J Pharmacol 1987; 141: 243-51.
153. + currents in pancreatic B-cells. Naunyn Schmiedebergs Arch Pharmacol 1988; 337: 225-30.
154. Panten U, Burgfeld J, Goerke F, Rennicke M, Schwanstecher M, Wallasch A, et al. 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: 1217-29.
155. Hansen AM, Christensen IT, Hansen JB, Carr RD, Ashcroft FM, Wahl P. Differential interactions of nateglinide and repaglinide on the human beta-cell sulphonylurea receptor 1. Diabetes 2002; 51: 2789-95.
156. +-channels by a sulfonylurea analogue with a phosphate group. Biochem Pharmacol 2003; 65: 599-602.
157. ATP channel isoforms. J Biol Chem 1999; 274: 11587-92.
158. + channel openers. J Biol Chem 2000; 275: 717-20.
159. ATP channel closure. FEBS Lett 1999; 459: 367-76.
160. ATP channels. Biochem Biophys Res Comm 1999; 255: 231-8.
161. ATP channels: control of nucleotide sensitivity by the N-terminal domain of the Kir6.2 subunit. J Physiol 1999; 515 (Pt 1): 19-30.
162. Reimann F, Tucker SJ, Proks P, Ashcroft PM. Involvement of the n-terminus of Kir6.2 in coupling to the sulphonylurea receptor. J Physiol 1999; 518 (Pt 2): 325-36.
163. Babenko AP, Sharma N, Aguilar-Bryan L, Gonzalez G. In Molecular Pathogenesis of MODYs, Matschinsky FM, Magnuson MA, eds.; Karger: New York, 2000, Vol 15, pp. 44-60.
164. Dorschner H, Brekardin E, Uhde I, Schwanstecher C, Schwanstecher M. Stoichiometry of sulfonylurea-induced ATP-sensitive potassium channel closure. Mol Pharmacol 1999; 55: 1060-6.
165. Matsuo M, Tanabe K, Kioka N, Amachi T, Ueda K. Different binding properties and affinities for ATP and ADP among sulfonylurea receptor subtypes, SUR1, SUR2A, and SUR2B. J Biol Chem 2000; 275: 28757-63.
166. + channels. Circ Res 2000; 87: 873-80.
167. + channel openers: homology model of sulfonylurea receptor carboxyl-termini. Nippon Yakurigaku Zasshi 2001; 118: 177-86.
168. + channel openers. Mol Pharmacol 1999; 56: 308-15.
169. Uhde I, Toman A, Gross I, Schwanstecher C, Schwanstecher M. Identification of the potassium channel opener site on sulfonylurea receptors. J Biol Chem 1999; 274: 28079-82.
170. ATP channel openers. EMBO J 2000; 19: 6644-51.
171. Dabrowski M, Ashcroft FM, Ashfield R, Lebrun P, Pirotte B, Egebjerg J, et al. 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: 1896-906.
172. Loo TW, Clarke DM. The packing of the transmembrane segments of human multidrug resistance P-glycoprotein is revealed by disulfide cross-linking analysis. J Biol Chem 2000; 275: 5253-6.
173. ATP channel modulators in rat cardiac membranes. Br J Pharmacol 1998; 123: 1395-402.
174. Dickinson KE, Bryson CC, Cohen RB, Rogers L, Green DW, Atwal KS. Nucleotide regulation and characteristics of potassium channel opener
175. Schwanstecher M, Sieverding C, Dorschner H, Gross I, Aguilar-Bryan L, Schwanstecher C, et al. Potassium channel openers require ATP to bind to and act through sulfonylurea receptors. EMBO J 1995; 17: 5529-35.
176. Schwanstecher M, Schwanstecher C, Dickel C, Chudziak F, Moshiri A, Panten U. Location of the sulphonylurea receptor at the cytoplasmic face of the beta-cell membrane. British Journal of Pharmacology 1991; 113: 903-11.
177. ATP channel. Diabetes 1999; 48: 1341-7.
178. Hambrock A, Loffler-Walz C, Russ U, Lange U, Quast U. Characterization of a mutant sulfonylurea receptor SUR2B with high affinity for sulfonylureas and openers: differences in the coupling to Kir6.x subtypes. Mol Pharmacol 2001; 60: 190-9.
179. 125I labelled azido-substituted glibenclamide analogue for photoaffinity labelling of the sulfonylurea receptor. J Labelled Compd Radiopharm 1994; 34: 675-80.
180. Schwanstecher M, Loser S, Chudziak F, Bachmann C, Panten U. Photoaffinity labeling of the cerebral sulfonylurea receptor using a novel radioiodinated azidoglibenclamide analogue. Journal Of Neurochemistry 1994; 63: 698-708.
181. Schwanstecher M, Loser S, Chudziak F, Panten U. Identification of a 38-kDa high affinity sulfonylurea-binding peptide in insulin-secreting cells and cerebral cortex. J Biol Chem 1994; 269: 17768-71.
182. ATP channel. FEBS Lett 2001; 499: 154-60.
183. Bakos E, Evers R, Szakacs G, Tusnady GE, Welker E, Szabo K, et al. Functional multidrug resistance protein (MRP1) lacking the N-terminal transmembrane domain. J Biol Chem 1998; 273: 32167-75.
184. Qian YM, Qiu W, Gao M, Westlake CJ, Cole SP, Deeley RG. Characterization of binding of leukotriene C4 by human multidrug resistance protein 1: evidence of differential interactions with NH2- and COOH-proximal halves of the protein. J Biol Chem 2001; 276: 38636-44.
185. Greenberger LM. Major photoaffinity drug labeling sites for iodoaryl azidoprazosin in P-glycoprotein are within, or immediately C-terminal to, transmembrane domains 6 and 12. J Biol Chem 1993; 268: 11417-25.
186. Borchers C, Ulrich WR, Klemm K, Ise W, Gekeler V, Haas S, et al. B9209-005, an azido derivative of the chemosensitizer dexniguldipine-HCl, photolabels P-glycoprotein. Mol Pharmacol 1995; 48: 21-9.
187. Dey S, Ramachandra M, Pastan I, Gottesman MM, Ambudkar SV. Photoaffinity labeling of human P-glycoprotein: effect of modulator interaction and ATP hydrolysis on substrate binding. Methods Enzymol 1998; 292: 318-28.
188. Bakos E, Evers R, Calenda G, Tusnady GE, Szakacs G, Varadi A, et al. Characterization of the amino-terminal regions in the human multidrug resistance protein (MRP1). J Cell Sci 2000; 113 Pt 24: 4451-61.
189. Wouters J, Ooms F. Small molecule crystallography in drug design. Curr Pharm Des 2001; 7: 529-45.
190. Byrn SR, McKenzie AT, Hassan MM, Al-Badr AA. Conformation of glyburide in the solid state and in solution. J Pharm Sci 1986; 75: 596-600.
191. Lins L, Brasseur R, Malaisse WJ. Conformational analysis of non-sulfonylurea hypoglycemic agents of the meglitinide family. Biochem Pharmacol 1995; 50: 1879-84.
192. Pang SS, Guddat LW, Duggleby RG. Molecular basis of sulfonylurea herbicide inhibition of acetohydroxyacid synthase. J Biol Chem 2003; 278: 7639-44.
193. Bartholomew DM, Van Dyk DE, Lau SM, O'Keefe DP, Rea PA, Viitanen PV. Alternate energy-dependent pathways for the vacuolar uptake of glucose and glutathione conjugates. Plant Physiol 2002; 130: 1562-72.
194. Wouters J, Michaux C, Durant F, Dogne JM, Delarge J, Masereel B. Isosterism among analogues of torasemide: conformational, electronic and lipophilic properties. Eur J Med Chem 2000; 35: 923-9.
195. Ueda K, Komine J, Matsuo M, Seino S, Amachi T. Cooperative binding of ATP and MgADP in the sulfonylurea receptor is modulated by glibenclamide. Proc Natl Acad Sci USA 1999; 96: 1268-72.
196. Gribble FM, Tucker SJ, Ashcroft FM. The essential role of the Walker A motifs of SUR1 in K-ATP channel activation by Mg-ADP and diazoxide. EMBO J 1997; 16: 1145-52.
197. Huang X, Liu H, Cui M, Fu W, Yu K, Chen K, et al. Simulating the interactions of toxins with K+ channels. Curr Pharm Design 2004; 10(9): 1057-67.
198. Wassermann GF, Loss ES. Testosterone action on the Sertoli cell membrane: a KIR6.x channel related effect. Curr Pharm Design 2004; 10(21): 2649-56.
199. Woods SC, Seeley RJ, Baskin DG, Schwartz MW. Insulin and the blood-brain barrier. Curr Pharm Design 2003: 9(10): 795-800.