Thioglycosides as inhibitors of hSGLT1 and hSGLT2: Potential therapeutic agents for the control of hyperglycemia in diabetes

International Journal of Medical Sciences

Volumn 4, Issue 3, 2007, Pages 131-139

  Castaneda, Francisco ^a   Burse, Antje ^b   Boland, Wilhelm ^b   Kinne, Rolf K H ^a  

^a MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

^b MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

Author keywords

Diabetes; Fluorescence resonance energy transfer; Hyperglycemia; Sodium dependent glucose transport; Thioglycoside; methyl glucoside uptake

Indexed keywords

ALPHA METHYLGLUCOSIDE; PHLORIZIN; SODIUM GLUCOSE COTRANSPORTER 1; SODIUM GLUCOSE COTRANSPORTER 2; THIOGLYCOSIDE; THIOGLYCOSIDE 1; THIOGLYCOSIDE 2; THIOGLYCOSIDE 3; THIOGLYCOSIDE 4; THIOGLYCOSIDE 5; THIOGLYCOSIDE 6; THIOGLYCOSIDE 7; UNCLASSIFIED DRUG; SLC5A1 PROTEIN, HUMAN; SLC5A2 PROTEIN, HUMAN;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DIABETES MELLITUS; DISEASE CONTROL; DRUG EFFECT; DRUG INHIBITION; DRUG MECHANISM; FLUORESCENCE RESONANCE ENERGY TRANSFER; HYPERGLYCEMIA; IC 50; MEMBRANE DEPOLARIZATION; MEMBRANE POTENTIAL; NONHUMAN; PROTEIN EXPRESSION; ANIMAL; CHO CELL; CRICETULUS; DRUG ANTAGONISM; HAMSTER; HUMAN; SYNTHESIS;

ANIMALS; CHO CELLS; CRICETINAE; CRICETULUS; DIABETES MELLITUS; HUMANS; HYPERGLYCEMIA; SODIUM-GLUCOSE TRANSPORTER 1; SODIUM-GLUCOSE TRANSPORTER 2; THIOGLYCOSIDES;

EID: 34248191309     PISSN: None     EISSN: 14491907     Source Type: Journal    
DOI: 10.7150/ijms.4.131     Document Type: Article

References (44)

1. Del Prato S, Matsuda M, Simonson DC, et al. Studies on the mass action effect of glucose in NIDDM and IDDM: evidence for glucose resistance. Diabetologia. 1997; 40: 687-697.
2. Bonadonna RC. Alterations of glucose metabolism in type 2 diabetes mellitus. An overview. Rev Endocr Metab Disord. 2004; 5: 89-97.
3. Klein R. Hyperglycemia and microvascular and macrovascular disease in diabetes. Diabetes Care. 1995; 18: 258-268.
4. Haffner SJ, and Cassells H. Hyperglycemia as a cardiovascular risk factor. The American Journal of Medicine. 2003; 115: 6S-11S.
5. Porte D Jr, and Schwartz MW. Diabetes complications: why is glucose potentially toxic? Science. 1996; 272: 699-700.
6. Robertson RP, Harmon J, Tran PO, et al. Glucose toxicity in beta-cells: type 2 diabetes, good radicals gone bad, and the glutathione connection. Diabetes. 2003; 52: 581-587.
7. Bell DS. Type 2 diabetes mellitus: what is the optimal treatment regimen? Am J Med. 2004; 116: 23S-29S.
8. Wagman AS, and Nuss JM. Current therapies and emerging targets for the treatment of diabetes. Current Pharmaceutical Design. 2001; 7: 417-450.
9. Wood IS, and Trayhurn P. Glucose transporters (GLUT and SGLT): expanded families of sugar transport proteins. British Journal of Nutrition. 2003; 89: 3-9.
10. Wright EM, and Turk E. The sodium/glucose cotransport family SLC5. Pflugers Arch. 2004; 447: 510-518.
11. Wright EM. Renal Na(+)-glucose cotransporters. American Journal of Physiology: Renal Physiology. 2001; 280: F10-F18.
12. Tsujihara K, Hongu M, Saito K, et al. Na(+)-glucose cotransporter inhibitors as antidiabetics. I. Synthesis and pharmacological properties of 4'-dehydroxyphlorizin derivatives based on a new concept. Chem Pharm Bull (Tokyo). 1996; 44: 1174-1180.
13. Hongu M, Tanaka T, Funami N, et al. Na(+)-glucose cotransporter inhibitors as antidiabetic agents. II. Synthesis and structure-activity relationships of 4′-dehydroxyphlorizin derivatives. Chemical & Pharmaceutical Bulletin (Tokyo). 1998; 46: 22-33.
14. Hongu M, Funami N, Takahashi Y, et al. Na(+)-glucose cotransporter inhibitors as antidiabetic agents. III. Synthesis and pharmacological properties of 4′-dehydroxyphlorizin derivatives modified at the OH groups of the glucose moiety. Chemical & Pharmaceutical Bulletin (Tokyo). 1998; 46: 1545-1555.
15. Asano T, Ogihara T, Katagiri H, et al. Glucose transporter and Na+/glucose cotransporter as molecular targets of anti-diabetic drugs. Curr Med Chem. 2004; 11: 2717-2724.
16. Ehrenkranz JR, Lewis NG, Kahn CR, et al. Phlorizin: a review. Diabetes Metab Res Rev. 2005; 21: 31-38.
17. Nunoi K, Yasuda K, Adachi T, et al. Beneficial effect of T-1095, a selective inhibitor of renal Na+-glucose cotransporters, on metabolic index and insulin secretion in spontaneously diabetic GK rats. Clinical and Experimental Pharmacology and Physiology. 2002; 29: 386-390.
18. Tsujihara K, Hongu M, Saito K, et al. Na(+)-glucose cotransporter (SGLT) inhibitors as antidiabetic agents. 4. Synthesis and pharmacological properties of 4′-dehydroxyphlorizin derivatives substituted on the B ring. Journal of Medicinal Chemistry. 1999; 42: 5311-5324.
19. Ohsumi K, Matsueda H, Hatanaka T, et al. Pyrazole-O-glucosides as novel Na(+)-glucose cotransporter (SGLT) inhibitors. Bioorganic& Medicinal Chemistry Letters. 2003; 13: 2269-2272.
20. Oku A, Ueta K, Arakawa K, et al. T-1095, an inhibitor of renal Na+-glucose cotransporters, may provide a novel approach to treating diabetes. Diabetes. 1999; 48: 1794-1800.
21. Oku A, Ueta K, Nawano M, et al. Antidiabetic effect of T-1095, an inhibitor of Na(+)-glucose cotransporter, in neonatally streptozotocin-treated rats. European Journal of Pharmacology. 2000; 391: 183-192.
22. Oku A, Ueta K, Arakawa K, et al. Antihyperglycemic effect of T-1095 via inhibition of renal Na+-glucose cotransporters in streptozotocin-induced diabetic rats. Biological and Pharmaceutical Bulletin. 2000; 23: 1434-1437.
23. Arakawa K, Ishihara T, Oku A, et al. Improved diabetic syndrome in C57BL/KsJ-db/db mice by oral administration of the Na(+)-glucose cotransporter inhibitor T-1095. British Journal of Pharmacology. 2001; 132: 578-586.
24. Oku A, Ueta K, Arakawa K, et al. Correction of hyperglycemia and insulin sensitivity by T-1095, an inhibitor of renal Na+-glucose cotransporters, in streptozotocin-induced diabetic rats. Jpn J Pharmacol. 2000; 84: 351-354.
25. Ueta K, Ishihara T, Matsumoto Y, et al. Long-term treatment with the Na+-glucose cotransporter inhibitor T-1095 causes sustained improvement in hyperglycemia and prevents diabetic neuropathy in Goto-Kakizaki Rats. Life Sci. 2005; 76: 2655-2668.
26. Nawano M, Oku A, Ueta K, et al. Hyperglycemia contributes insulin resistance in hepatic and adipose tissue but not skeletal muscle of ZDF rats. American Journal of Physiology: Endocrinology and Metabolism. 2000; 278: E535-543.
27. Mizuma T, Hagi K, and Awazu S. Intestinal transport of beta-thioglycosides by Na+/glucose cotransporter. J Pharm Pharmacol. 2000; 52: 303-310.
28. Hirayama BA, Lostao MP, Panayotova-Heiermann M, et al. Kinetic and specificity differences between rat, human, and rabbit Na+- glucose cotransporters (SGLT-1). American Journal of Physiology: Gastrointestinal and Liver Physiology. 1996; 270: G919-G926.
29. Castaneda F, and Kinne RKH. A 96-well automated method to study inhibitors of human sodium-dependent D-glucose transport. Molelcular and Cellular Biochemistry. 2005; 280: 91-98.
30. Shirota K, Kato Y, Suzuki K, et al. Characterization of novel kidney-specific delivery system using an alkylglucoside vector. J Pharmacol Exp Ther. 2001; 299: 459-467.
31. Feld BK, Pasteels JM, and Boland W. Phaedon cochleariae and Gastrophysa viridula (Coleoptera:Chrysomelidae) produce defensive iridoid monoterpenes de novo and are able to sequester glycosidically bound terpenoid precursors. Chemoecology. 2001; 11: 191-198.
32. Kuhn J, Pettersson EM, Feld BK, et al. Selective transport systems mediate sequestration of plant glucosides in leaf beetles: A molecular basis for adaptation and evolution. Proc Natl Acad Sci U S A. 2004; 101: 13808-13813.
33. Kuhn J, Pettersson EM, Feld BK, et al. Sequestration of Plant-Derived Phenolglucosides by Larvae of the Leaf Beetle Chrysomela populi: Thioglucosides as Mechanistic Probes. In press.
34. Scheen AJ. Is there a role for alpha-glucosidase inhibitors in the prevention of type 2 diabetes mellitus? Drugs. 2003; 63: 933-951.
35. Suzuki K, Susaki H, Okuno S, et al. Renal drug targeting using a vector "alkylglycoside". J Pharmacol Exp Ther. 1999; 288: 57-64.
36. Suzuki K, Ando T, Susaki H, et al. Structural requirements for alkylglycoside-type renal targeting vector. Pharm Res. 1999; 16: 1026-1034.
37. Vestri S, Okamoto MM, de Freitas HS, et al. Changes in sodium or glucose filtration rate modulate expression of glucose transporters in renal proximal tubular cells of rat. Journal of Membrane Biology. 2001; 182: 105-112.
38. Meyer C, Stumvoll M, Nadkarni V, et al. Abnormal renal and hepatic glucose metabolism in type 2 diabetes mellitus. J Clin Invest. 1998; 102: 619-624.
39. Dominguez JH, Camp K, Maianu L, et al. Molecular adaptations of GLUT1 and GLUT2 in renal proximal tubules of diabetic rats. Am J Physiol. 1994; 266: F283-290.
40. Burckhardt G, and K.H KR. Transport proteins. Cotransporters and countertransportes. In: Handbook of Physiology - Renal Physiology. New York: Oxford University Press. 1992: 2083-2117.
41. Au A, Gupta A, Schembri P, et al. Rapid insertion of GLUT2 into the rat jejunal brush-border membrane promoted by glucagon-like peptide 2. Biochemical Journal. 2002; 367: 247-254.
42. Marks J, Debnam ES, Dashwood MR, et al. Detection of glucagon receptor mRNA in the rat proximal tubule: potential role for glucagon in the control of renal glucose transport. Clin Sci (Lond). 2003; 104: 253-258.
43. Diez-Sampedro A, Lostao MP, Wright EM, et al. Glycoside binding and translocation in Na(+)-dependent glucose cotransporters: comparison of SGLT1 and SGLT3. The Journal of Membrane Biology. 2000; 176: 111-117.
44. Santer R, Kinner M, Lassen CL, et al. Molecular analysis of the SGLT2 gene in patients with renal glucosuria. Journal of the American Society of Nephrology. 2003; 14: 2873-2882.