Discovery of non-glycoside sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors by ligand-based virtual screening

Journal of Medicinal Chemistry

Volumn 53, Issue 24, 2010, Pages 8770-8774

  Wu, Jian Sung ^a   Peng, Yi Hui ^a   Wu, Jiun Ming ^a   Hsieh, Chieh Jui ^a   Wu, Szu Huei ^a   Coumar, Mohane Selvaraj ^a   Song, Jen Shin ^a   Lee, Jinq Chyi ^a   Tsai, Chi Hui ^a   Chen, Chiung Tong ^a   Liu, Yu Wei ^a   Chao, Yu Sheng ^a   Wu, Su Ying ^a  

^a NATIONAL HEALTH RESEARCH INSTITUTES   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; SODIUM GLUCOSE COTRANSPORTER 2; SODIUM GLUCOSE COTRANSPORTER 2 INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; DRUG SCREENING; DRUG STRUCTURE; MOLECULAR MODEL; NONHUMAN; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION;

ANIMALS; BENZIMIDAZOLES; CHO CELLS; CLUSTER ANALYSIS; COMPUTER SIMULATION; CRICETINAE; CRICETULUS; DATABASES, FACTUAL; DRUG DESIGN; GLYCOSIDES; LIGANDS; MODELS, MOLECULAR; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; SODIUM-GLUCOSE TRANSPORTER 2;

EID: 78650346635     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101080v     Document Type: Article

References (25)

1. International Diabetes Federation. Diabetes Atlas, 3 rd ed; Internatinal Diabetes Federation: Brussels, Belgium, 2006.
2. Porte, D., Jr. Clinical importance of insulin secretion and its interaction with insulin resistance in the treatment of type 2 diabetes mellitus and its complications Diabetes Metab. Res. Rev. 2001, 17, 181-188
3. Washburn, W. N. Development of the renal glucose reabsorption inhibitors: a new mechanism for the pharmacotherapy of diabetes mellitus type 2 J. Med. Chem. 2009, 52, 1785-1794
4. UK Prospective Diabetes Study (UKPDS) Group. Effect of intensive blood-glucose control with metformin on complications in overweight patients with type 2 diabetes (UKPDS 34) Lancet 1998, 352, 854-865
5. Marsenic, O. Glucose control by the kidney: an emerging target in diabetes Am. J. Kidney Dis. 2009, 53, 875-883
6. +/glucose cotransporter SGLT2 reveal a common mechanism for SGLT1 and SGLT2 J. Biol. Chem. 1996, 271, 32678-32683
7. Wright, E. M.; Hirayama, B.; Hazama, A.; Loo, D. D.; Supplisson, S.; Turk, E.; Hager, K. M. The sodium/glucose cotransporter (SGLT1) Soc. Gen. Physiol. Ser. 1993, 48, 229-241
8. Chao, E. C.; Henry, R. R. SGLT2 inhibition - a novel strategy for diabetes treatment Nat. Rev. Drug Discovery 2010, 9, 551-559
9. +, d -glucose cotransporter. A model Biochim. Biophys. Acta 1982, 688, 557-571
10. +-glucose cotransporters in streptozotocin-induced diabetic rats Biol. Pharm. Bull. 2000, 23, 1434-1437
11. Fujimori, Y.; Katsuno, K.; Ojima, K.; Nakashima, I.; Nakano, S.; Ishikawa-Takemura, Y.; Kusama, H.; Isaji, M. Sergliflozin etabonate, a selective SGLT2 inhibitor, improves glycemic control in streptozotocin-induced diabetic rats and Zucker fatty rats Eur. J. Pharmacol. 2009, 609, 148-154
12. Fujimori, Y.; Katsuno, K.; Nakashima, I.; Ishikawa-Takemura, Y.; Fujikura, H.; Isaji, M. Remogliflozin etabonate, in a novel category of selective low-affinity sodium glucose cotransporter (SGLT2) inhibitors, exhibits antidiabetic efficacy in rodent models J. Pharmacol. Exp. Ther. 2008, 327, 268-276
13. Rossetti, L.; Smith, D.; Shulman, G. I.; Papachristou, D.; DeFronzo, R. A. Correction of hyperglycemia with phlorizin normalizes tissue sensitivity to insulin in diabetic rats J. Clin. Invest. 1987, 79, 1510-1515
14. Ehrenkranz, J. R.; Lewis, N. G.; Kahn, C. R.; Roth, J. Phlorizin: a review Diabetes Metab. Res. Rev. 2005, 21, 31-38
15. Meng, W.; Ellsworth, B. A.; Nirschl, A. A.; McCann, P. J.; Patel, M.; Girotra, R. N.; Wu, G.; Sher, P. M.; Morrison, E. P.; Biller, S. A.; Zahler, R.; Deshpande, P. P.; Pullockaran, A.; Hagan, D. L.; Morgan, N.; Taylor, J. R.; Obermeier, M. T.; Humphreys, W. G.; Khanna, A.; Discenza, L.; Robertson, J. G.; Wang, A.; Han, S.; Wetterau, J. R.; Janovitz, E. B.; Flint, O. P.; Whaley, J. M.; Washburn, W. N. Discovery of dapagliflozin: a potent, selective renal sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes J. Med. Chem. 2008, 51, 1145-1149
16. Wilding, J.; Woo, V.; Soler, N.; Pahor, A.; Sugg, J.; Parikh, S. Dapagliflozin in Patients with Type 2 Diabetes Poorly Controlled on Insulin Therapy - Efficacy of a Novel Insulin-Independent Treatment. American Diabetes Association: Alexandria, VA, 2010; Abstract 0078-OR, http://ww2.aievolution.com/ ada1001/index.cfm?do=abs.viewAbs&abs=12779.
17. Rosenstock, J.; Arbit, D.; Usiskn, K.; Capuano, G.; Canovatchel, W. Canagliflozin, an Inhibitor of Sodium Glucose Co-Transporter 2 (SGLT2), Improves Glycemic Control and Lowers Body Weight in Subjects with Type 2 Diabetes (T2D) on Metformin. American Diabetes Association: Alexandria, VA, 2010; Abstract 0077-OR, http://ww2.aievolution.com/ada1001/index.cfm?do=abs.viewAbs&abs= 12778.
18. Kashiwagi, A.; Utsuno, A.; Kazuta, K.; Yoshida, S.; Kageyama, S. ASP1941, a Novel, Selective Sodium-Glucose Co-Transporter (SGLT) 2 Inhibitor, Was Investigated in the Japanese Population. American Diabetes Association: Alexandria, VA, 2010; Abstract 0075-OR, http://ww2.aievolution.com/ada1001/ index.cfm?do=abs.viewAbs&abs=12776.
19. Ernst, B.; Magnani, J. L. From carbohydrate leads to glycomimetic drugs Nat. Rev. Drug Discovery 2009, 8, 661-677
20. +-glucose cotransporter (SGLT) inhibitory flavonoids from the roots of Sophora flavescens Bioorg. Med. Chem. 2007, 15, 3445-3449
21. +-glucose cotransporter (SGLT) inhibitors from Acer nikoense Bioorg. Med. Chem. Lett. 2010, 20, 1070-1074
22. Arai, H.; Hirasawa, Y.; Rahman, A.; Kusumawati, I.; Zaini, N. C.; Sato, S.; Aoyama, C.; Takeo, J.; Morita, H. Alstiphyllanines E-H, picraline and ajmaline-type alkaloids from Alstonia macrophylla inhibiting sodium glucose cotransporter Bioorg. Med. Chem. 2010, 18, 2152-2158
23. Martin, Y. C.; Bures, M. G.; Danaher, E. A.; DeLazzer, J.; Lico, I.; Pavlik, P. A. A fast new approach to pharmacophore mapping and its application to dopaminergic and benzodiazepine agonists J. Comput.-Aided Mol. Des. 1993, 7, 83-102
24. Washburn, W. N. Evolution of sodium glucose co-transporter 2 inhibitors as anti-diabetic agents Expert. Opin. Ther. Pat. 2009, 19, 1485-1499
25. Kirchmair, J.; Distinto, S.; Markt, P.; Schuster, D.; Spitzer, G. M.; Liedl, K. R.; Wolber, G. How to optimize shape-based virtual screening: choosing the right query and including chemical information J. Chem. Inf. Model. 2009, 49, 678-692