Kinetics Studies on the Inhibition Mechanism of Pancreatic α-Amylase by Glycoconjugated 1H-1,2,3-Triazoles: A New Class of Inhibitors with Hypoglycemiant Activity

ChemBioChem

Volumn 13, Issue 11, 2012, Pages 1584-1593

  Senger, Mario Roberto ^a   Gomes, Lucas da Costa Andrade ^a   Ferreira, Sabrina Baptista ^b   Kaiser, Carlos Roland ^b   Ferreira, Vitor Francisco ^c   Silva, Floriano Paes ^a  

^a INSTITUTO OSWALDO CRUZ   (Brazil)

^b FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^c FLUMINENSE FEDERAL UNIVERSITY   (Brazil)

Author keywords

Amylase; Drug design; Glycoconjugates; Inhibition mechanisms; Triazoles; Type 2 diabetes

Indexed keywords

ALPHA AMYLASE PANCREAS ISOENZYME; ANTIDIABETIC AGENT; GLYCOCONJUGATED 1H 1,2,3 TRIAZOLE DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIDIABETIC ACTIVITY; ARTICLE; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; PANCREAS; PRIORITY JOURNAL;

ANIMALS; DIABETES MELLITUS, TYPE 2; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; HYPOGLYCEMIC AGENTS; KINETICS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PANCREATIC ALPHA-AMYLASES; STRUCTURE-ACTIVITY RELATIONSHIP; SWINE; TRIAZOLES;

MAMMALIA; RATTUS; SUS;

EID: 84863995152     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201200272     Document Type: Article

References (33)

1. S. Wild, G. Roglic, A. Green, R. Sicree, H. King, Diabetes Care 2004, 27, 1047-1053.
2. N. J. Wareham, Endocrinol. Nutr. 2009, 56, 60-62.
3. G. Roglic, N. Unwin, P. H. Bennett, C. Mathers, J. Tuomilehto, S. Nag, V. Connolly, H. King, Diabetes Care 2005, 28, 2130-2135; S. Yamagishi, T. Matsui, S. Ueda, K. Fukami, S. Okuda, Curr. Drug Metab. 2009, 10, 159-163.
4. D. J. Calhoun, T. W. Trimarco, R. J. Meek, D. A. Locasto, J. Emerg. Med. Serv. 2011, 36, 32-34.
5. P. J. Phillips, S. M. Twigg, Aust. Fam. Physician 2010, 39, 651-653.
6. R. Tundis, M. R. Loizzo, F. Menichini, Mini-Rev. Med. Chem. 2010, 10, 315-331.
7. J. F. Robyt, D. French, J. Biol. Chem. 1970, 245, 3917-3927.
8. J. D. McCarter, S. G. Withers, Curr. Opin. Struct. Biol. 1994, 4, 885-892.
9. H. M. Jespersen, E. A. MacGregor, M. R. Sierks, B. Svensson, Biochem. J. 1991, 280, 51-55.
10. L. Pasero, Y. Mazzéi-Pierron, B. Abadie, Y. Chicheportiche, G. Marchis-Mouren, Biochim. Biophys. Acta Protein Struct. Mol. Enzymol. 1986, 869, 147-157.
11. P. Cozzone, L. Paséro, G. Marchis-Mouren, Biochim. Biophys. Acta Protein Struct. 1970, 200, 590-593.
12. Y. Narita, K. Inouye, J. Agric. Food Chem. 2009, 57, 9218-9225.
13. M. Qian, S. Spinelli, H. Driguez, F. Payan, Protein Sci. 1997, 6, 2285-2296.
14. Y. Sakano, H. Taniguchi, G. Okada, M. Ohnishi, Tanpakushitsu Kakusan Koso 1985, 30, 299-302.
15. D. D. Schmidt, W. Frommer, B. Junge, L. Müller, W. Wingender, E. Truscheit, D. Schäfer, Naturwissenschaften 1977, 64, 535-536.
16. R. Tattersall, Diabetic Med. 1993, 10, 688-693.
17. M. Al kazaz, V. Desseaux, G. Marchis-Mouren, F. Payan, E. Forest, M. Santimone, Eur. J. Biochem. 1996, 241, 787-796; M. Al kazaz, V. Desseaux, G. Marchis-Mouren, E. Prodanov, M. Santimone, Eur. J. Biochem. 1998, 252, 100-107; C. Li, A. Begum, S. Numao, K. H. Park, S. G. Withers, G. D. Brayer, Biochemistry 2005, 44, 3347-3357; M.- J. Kim, S.-B. Lee, H.-S. Lee, S.-Y. Lee, J.-S. Baek, D. Kim, T.-W. Moon, J. F. Robyt, K.-H. Park, Arch. Biochem. Biophys. 1999, 371, 277-283; R. Koukiekolo, V. Desseaux, Y. Moreau, G. Marchis-Mouren, M. Santimone, Eur. J. Biochem. 2001, 268, 841-848; S.-H. Yoon, J. F. Robyt, Carbohydr. Res. 2003, 338, 1969-1980.
18. G. J. Davies, S. P. Tolley, B. Henrissat, C. Hjort, M. Schülein, Biochemistry 1995, 34, 16210-16220.
19. D. J. Vocadlo, G. J. Davies, Curr. Opin. Chem. Biol. 2008, 12, 539-555.
20. V. H. Lillelund, H. H. Jensen, X. Liang, M. Bols, Chem. Rev. 2002, 102, 515-554.
21. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711; Angew. Chem. Int. Ed. 2002, 41, 2596-2599; C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064; H. C. Kolb, K. B. Sharpless, Drug Discovery Today 2003, 8, 1128-1137.
22. S. B. Ferreira, A. C. R. Sodero, M. F. C. Cardoso, E. S. Lima, C. R. Kaiser, F. P. Silva, V. F. Ferreira, Med. Chem. 2010, 53, 2364-2375.
23. R. Périon, V. Ferrières, M. I. García-Moreno, C. Ortiz Mellet, R. Duval, J. M. García Fernández, D. Plusquellec, Tetrahedron 2005, 61, 9118-9128; L. L. Rossi, A. Basu, Bioorg. Med. Chem. Lett. 2005, 15, 3596-3599; K. Slámová, P. Marhol, K. Bezouška, L. Lindkvist, S. G. Hansen, V. Křen, H. H. Jensen, Bioorg. Med. Chem. Lett. 2010, 20, 4263-4265; S. Dedola, D. L. Hughes, S. A. Nepogodiev, M. Rejzek, R. A. Field, Carbohydr. Res. 2010, 345, 1123-1134; N. Anand, N. Jaiswal, S. K. Pandey, A. K. Srivastava, R. P. Tripathi, Carbohydr. Res. 2011, 346, 16-25.
24. M. Balba, N. A. El-Hady, N. Taha, N. Rezki, E. S. H. El Ashry, Eur. J. Med. Chem. 2011, 46, 2596-2601.
25. C. Abad-Zapatero, Expert Opin. Drug Discovery 2007, 2, 469-488.
26. M. Alkazaz, V. Desseaux, G. Marchis-Mouren, F. Payan, E. Forest, M. Santimone, Eur. J. Biochem. 1996, 241, 787-796.
27. E. R. Wilcox, J. R. Whitaker, Biochemistry 1984, 23, 1783-1791; G. H. Feng, M. Richardson, M. S. Chen, K. J. Kramer, T. D. Morgan, G. R. Reeck, Insect Biochem. Mol. Biol. 1996, 26, 419-426; A. M. Sefler, M. C. Kozlowski, T. Guo, P. A. Bartlett, J. Org. Chem. 1997, 62, 93-102; O. L. Franco, D. J. Rigden, F. R. Melo, C. Bloch, Jr., C. P. Silva, M. F. Grossi de Sá, Eur. J. Biochem. 2000, 267, 2166-2173; P. Geng, F. Qiu, Y. Zhu, G. Bai, Carbohydr. Res. 2008, 343, 882-892.
28. G. D. Brayer, G. Sidhu, R. Maurus, E. H. Rydberg, C. Braun, Y. Wang, N. T. Nguyen, C. M. Overall, S. G. Withers, Biochemistry 2000, 39, 4778-4791; M. Qian, S. Spinelli, H. Driguez, F. Payan, Protein Sci. 1997, 6, 2285-2296; K. D. Randell, T. P. Frandsen, B. Stoffer, M. A. Johnson, B. Svensson, B. M. Pinto, Carbohydr. Res. 1999, 321, 143-156; M. Westerfors, U. Tedebark, H. O. Andersson, S. Ohrman, D. Choudhury, O, Ersoy, Y. Shinohara, A. Axén, E. Carredano, H. Baumann, J. Mol. Recognit. 2003, 16, 396-405.
29. C. Seigner, E. Prodanov, G. Marchis-Mouren, Eur. J. Biochem. 1985, 148, 161-168.
30. M. Qian, R. Haser, G. Buisson, E. Duée, F. Payan, Biochemistry 1994, 33, 6284-6294; C. Gilles, J. P. Astier, G. Marchis-Mouren, C. Cambillau, F. Payan, Eur. J. Biochem. 1996, 238, 561-569; V. Nahoum, G. Roux, V. Anton, P. Rougé, A. Puigserver, H. Bischoff, B. Henrissat, F. Payan, Biochem. J. 2000, 346, 201-208; N. Aghajari, M. Roth, R. Haser, Biochemistry 2002, 41, 4273-4280; C. Li, A. Begum, S. Numao, K. H. Park, S. G. Withers, G. D. Brayer, Biochemistry 2005, 44, 3347-3357.
31. X. Qin, L. Ren, X. Yang, F. Bai, L. Wang, P. Geng, G. Bai, Y. Shen, J. Struct. Biol. 2011, 174, 196-202.
32. R. A. Copeland, Evaluation of Enzyme Inhibitors in Drug Discovery, Wiley, New York, 2005.
33. T. Yonetani, H. Theorell, Arch. Biochem. Biophys. 1964, 106, 243-251.