α-1-C-Butyl-1,4-Dideoxy-1,4-Imino-L-Arabinitol as a second-Generation iminosugar-based oral α-Glucosidase inhibitor for improving postprandial hyperglycemia

Journal of Medicinal Chemistry

Volumn 55, Issue 23, 2012, Pages 10347-10362

  Kato, Atsushi ^a   Hayashi, Erina ^a   Miyauchi, Saori ^a   Adachi, Isao ^a   Imahori, Tatsushi ^b   Natori, Yoshihiro ^b   Yoshimura, Yuichi ^b   Nash, Robert J ^c   Shimaoka, Hideyuki ^d   Nakagome, Izumi ^e   Koseki, Jun ^e   Hirono, Shuichi ^e   Takahata, Hiroki ^b  

^a UNIVERSITY OF TOYAMA   (Japan)

^b TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

^c Phytoquest Limited   (United Kingdom)

^d Simitomo Bakelite Company Limited ^*  (Japan)

^e KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 C DIBUTYL 1,4 IMINO LEVO ARABINITOL; ACARBOSE; ALPHA 1 C (1 HYDROXYBUTYL) 1,4 DIDEOXY 1,4 IMINO LEVO ARABINITOL; ALPHA 1 C (4 METHYLPENTYLL) 1,4 DIDEOXY 1,4 IMINO LEVO ARABINITOL; ALPHA 1 C (4 PHENYLBUTYL) 1,4 DIDEOXY 1,4 IMINO LEVO ARABINITOL; ALPHA 1 C BUTYL 1 DEOXYNOJIRIMYCIN; ALPHA 1 C BUTYL 1,4 DIDEOXY 1,4 IMINO LEVO ARABINITOL; ALPHA 1 C DECYL 1,4 DIDEOXY 1,4 IMINO LEVO ARABINITOL; ALPHA 1 C ETHYL 1,4 DIDEOXY 1,4 IMINO LEVO ARABINITOL; ALPHA 1 C HEPTYL 1,4 DIDEOXY 1,4 IMINO LEVO ARABINITOL; ALPHA 1 C HEXYL 1 DEOXYNOJIRIMYCIN; ALPHA 1 C HEXYL 1,4 DIDEOXY 1,4 IMINO LEVO ARABINITOL; ALPHA 1 C NONYL 1,4 DIDEOXY 1,4 IMINO LEVO ARABINITOL; ALPHA 1 C OCTYL 1 DEOXYNOJIRIMYCIN; ALPHA 1 C OCTYL 1,4 DIDEOXY 1,4 IMINO LEVO ARABINITOL; ALPHA 1 C PENTYL 1,4 DIDEOXY 1,4 IMINO LEVO ARABINITOL; ALPHA 1 C UNDECYL 1,4 DIDEOXY 1,4 IMINO LEVO ARABINITOL; ALPHA GLUCOSIDASE; ALPHA GLUCOSIDASE INHIBITOR; GLUCAN 1,4 ALPHA GLUCOSIDASE; GLUCOSE; GLUCOSYLCERAMIDASE; IMINOSUGAR; MIGLITOL; N BUTYL ALPHA 1 C BUTYL 1,4 DIDEOXY 1,4 IMINO LEVO ARABINITOL; OLIGO 1,6 GLUCOSIDASE; OLIGOSACCHARIDE; PLACEBO; SUCRASE; UNCLASSIFIED DRUG; VOGLIBOSE;

ALKYLATION; ANIMAL EXPERIMENT; ANIMAL MODEL; AREA UNDER THE CURVE; ARTICLE; ASYMMETRIC SYNTHESIS; CELL STRAIN HEPG2; COMPLEX FORMATION; CONTROLLED STUDY; CROSS COUPLING REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME SPECIFICITY; GLUCOSE BLOOD LEVEL; HUMAN; HUMAN CELL; HYPERGLYCEMIA; IC 50; MALE; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MAXIMUM PLASMA CONCENTRATION; MOLECULAR DOCKING; MOUSE; NONHUMAN; POSTPRANDIAL STATE; RING CLOSING METATHESIS; STEREOCHEMISTRY;

ADMINISTRATION, ORAL; ALPHA-GLUCOSIDASES; ANIMALS; ENZYME INHIBITORS; HUMANS; HYPERGLYCEMIA; HYPOGLYCEMIC AGENTS; IMINO SUGARS; INHIBITORY CONCENTRATION 50; MALE; MICE; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 84871027169     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301304e     Document Type: Article

References (69)

1. Tuomilehto, J.; Lindström, J.; Eriksson, J. G.; Valle, T. T.; Hämäläinen, H.; Ilanne-Parikka, P.; Keinänen-Kiukaanniemi, S.; Laakso, M.; Louheranta, A.; Rastas, M.; Salminen, V.; Uusitupa, M. (for the Finnish Diabetes Prevention Study Group). Prevention of type 2 diabetes mellitus by changes in lifestyle among subjects with impaired glucose tolerance. N. Engl. J. Med. 2001, 344, 1343-1350.
2. Lyssenko, V; Jonsson, A.; Almgren, P.; Pulizzi, N.; Isomaa, B.; Tuomi, T.; Berglung, G.; Alshuler, D.; Nilsson, P.; Groop, L. Clinical risk factors, DNA variants, and the development of type 2 diabetes N. Engl. J. Med. 2008, 359, 2220-2232
3. McCarthy, M. I. Genomics, type 2 diabetes, and obesity N. Engl. J. Med. 2010, 363, 2339-2350
4. Shaw, J. E.; Sicree, R. A.; Zimmet, P. Z. Global estimates of the prevalence of diabetes for 2010 and 2030 Diabetes Res. Clin. Pract. 2010, 87, 4-14
5. Gerich, J. E. Clinical significance, pathogenesis, and management of postprandial hyperglycemia Arch. Intern. Med. 2003, 163, 1306-1316
6. UK Prospective Diabetes Study Group. Intensive blood-glucose control with sulphonylureas or insulin compared with conventional treatment and risk of complications in patients with type 2 diabetes (UKPDS 33) Lancet 1998, 352, 837-853
7. UK Prospective Diabetes Study 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
8. Stratton, I. M.; Adler, A. I.; Neil, H. A. W.; Matthws, D. R.; Manley, S. E.; Cull, C. A.; Hadden, D.; Turner, R. C.; Holman, R. R. Association of glycaemia with macrovascular and microvascular complications of type 2 diabetes (UKPDS 35): prospective observational study BMJ [Br. Med. J.] 2000, 321, 405-412
9. Hanefeld, M.; Cagatay, M.; Petrowitsch, T.; Neuse, D.; Petzinna, D.; Rupp, M. Acarbose reduces the risk for myocardial infarction in type 2 diabetic patients: meta-analysis of seven long-term studies Eur. Heart J. 2004, 25, 10-16
10. Coutinho, M.; Gerstein, H. C; Wang, Y.; Yusuf, S. The relationship between glucose and incident cardiovascular events. A metaregression analysis of published data from 20 studies of 95,783 individuals followed for 12.4 years Diabetes Care 1999, 22, 233-240
11. Bonora, E.; Muggeo, M. Postprandial blood glucose as a risk factor for cardiovascular disease in type II diabetes: the epidemiological evidence Diabetologia 2001, 44, 2107-2114
12. Ceriello, A. Postprandial hyperglycemia and diabetes complications: is it time to treat? Diabetes 2005, 54, 1-7
13. Iwasa, M.; Yamada, Y.; Kobayashi, H.; Yasuda, S.; Kawamura, I.; Sumi, S.; Shiraki, T.; Yamaki, T.; Ushikoshi, H.; Hattori, A.; Aoyama, T.; Nishigaki, K.; Takemura, G.; Fujiwara, H; Minatoguchi, S. Both stimulation of GLP-1 recepters and inhibiton of glycogenolysis additively contribute to a protective effect of oral miglitol against ishaemia-reperfusion injury in rabbits Br. J. Pharmacol. 2011, 164, 119-131
14. Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application Tetrahedron: Asymmetry 2000, 11, 1645-1680
15. Sim, L.; Jayakanthan, K.; Mohan, S.; Nasi, R.; Johnston, B. D.; Pinto, B. M.; Rose, D. R. New glucosidase inhibitors from an ayurvedic herbal treatment for type 2 diabetes: structures and inhibition of human intestinal maltase-glucoamylase with compounds from Salacia reticulata Biochemistry 2010, 49, 443-451
16. Eskandari, R.; Jones, K.; Rose, D. R.; Pinto, B. M. Selectivity of 3′-O-methylponkoranol for inhibition of N- and C-terminal maltase glucoamylase and sucrase isomaltase, potential therapeutics for digestive disorders or their sequelae Bioorg. Med. Chem. Lett. 2011, 21, 6491-6494
17. Ogawa, S. Synthetic studies on glycosidase inhibitors composed of 5a-carba-sugars. Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, Germany, 1998; pp 87-106.
18. Horii, S.; Iwasa, T.; Mizuta, E.; Kameda, Y. Studies on validamycins, new antibiotics. VI. Validamine, hydroxyvalidamine and validatol, new cyclitols J. Antibiot. 1971, 24, 59-63
19. Kameda, Y.; Asano, N.; Yoshikawa, M.; Matsui, K. Valienamine as an α-glucosidase inhibitor J. Antibiot. 1980, 33, 1575-1576
20. Kameda, Y.; Asano, N.; Yoshikawa, M.; Takeuchi, M.; Yamaguchi, T.; Matsui, K. Valiolamine, a new α-glucosidase inhibiting aminocyclitol produced by Streptomyces hygroscopicus J. Antibiot. 1984, 37, 1301-1307
21. Horii, S; Fukase, H.; Matsuo, T.; Asano, N.; Matsui, K. Synthesis and α- d -glucosidase inhibitory activity of N-substituted valiolamine derivatives as potential oral antidiabetic agents J. Med. Chem. 1986, 29, 1038-1046
22. Kato, A.; Kato, N.; Kano, E.; Adachi, I.; Ikeda, K.; Yu, L.; Okamoto, T.; Banba, Y.; Ouchi, H.; Takahata, H.; Asano, N. Biological properties of d-and l -1-deoxyazasugars J. Med. Chem. 2005, 48, 2036-2044
23. Junge, B.; Matzke, M.; Stltefuss, J. In Handbook of Experimental Pharmacology; Kuhlmann, J.; Puls, W., Eds.; Springer-Verlag: New York, 1996; Vol. 119, p 411.
24. Cauderay, M.; Tappy, L.; Temler, E.; Jequier, E.; Hillebrand, I.; Felber, J. P. Effect of α-glucohydrolase inhibitors (Bay m1099 and Bay o1248) on sucrose metabolism in normal men Metabolism 1986, 35, 472-477
25. Madar, Z.; Olefsky, J. Effect of the α-glucosidase inhibitor Bay-O-1248 on the metabolic response of nondiabetic and diabetic rats to a high-carbogydrate diet Am. J. Clin. Nutr. 1986, 44, 206-211
26. Taylor, R. H.; Barker, H. M.; Bowey, E. A.; Canfield, J. E. Regulation of absorption of dietary carbohydrate in man by two new glycosidase inhibitors Gut 1986, 27, 1471-1478
27. Wisselaar, H. A.; van Dongen, J. M.; Reuser, A. J. Effects of N -hydroxyethyl-1-deoxynojirimycin (BAY m 1099) on the activity of neutral- and acid α-glucosidases in human fibroblasts and HepG2 cells Clin. Chim. Acta 1989, 182, 41-52
28. Putter, J. In Enzyme Inhibitors; Brodech, E., Ed.; Verlag Chemie: Weinheim, Germany, 1980; p 139.
29. Joubert, P. H.; Venter, H. L.; Foukaridis, G. N. The effect of miglitol and acarbose after an oral glucose load: a novel hypoglycaemic mechanism? Br. J. Clin. Pharmacol. 1990, 30, 391-396
30. Bischoff, H. Pharmacology of α-glucosidase inhibition Eur. J. Clin. Invest. 1994, 24, 3-10
31. Arh, H. J.; Boberg, M; Brendei, E.; Krause, H. P.; Steinke, W. Pharmacokinetics of miglitol. Absorption, distribution, metabolism, and excretion following administration to rats, dogs, and man Arzneimittelforschung 1997, 47, 734-745
32. Kreymann, B.; Williams, G.; Ghatei, M. A.; Bloom, S. R. Glucagon-like peptide-1 7-36: a physiological incretin in man Lancet 1987, 2, 1300-1304
33. Zander, M.; Madsbad, S.; Madsen, J. L.; Holst, J. J. Effect of 6-week course of glucagon-like peptide 1 on glycaemic control, insulin sensitivity, and beta-cell function in type 2 diabetes: a parallel-group study Lancet 2002, 359, 824-830
34. Asano, N.; Ikeda, K.; Yu, Li.; Kato, A.; Takebayashi, K.; Adachi, I.; Kato, I.; Ouchi, H.; Takahata, H.; Fleet, G. W. J. The l -enantiomers of d -sugar-mimicking iminosugars are noncompetitive inhibitors of d -glycohydrolase? Tetrahedron: Asymmetry 2005, 16, 223-229
35. da Cruz, F. P.; Newberry, S.; Jenkinson, S. F.; Wormald, M. R.; Butters, T. D.; Alonzi, D. S.; Nakagawa, S.; Becq, F.; Norez, C.; Nash, R. J.; Kato, A.; Fleet, G. W. J. 4-C-Me-DAB and 4-C-Me-LAB-enantiomeric alkyl-branched pyrrolidine iminosugars-are specific and potent α-glucosidase inhibitors; acetone as the sole protecting group Tetrahedron Lett. 2011, 52, 219-223
36. Natori, Y.; Imahori, T.; Murakami, K.; Yoshimura, Y.; Nakagawa, S.; Kato, A.; Adachi, I.; Takahata, H. The synthesis and biological evaluation of 1- C -alkyl- l -arabinoiminofuranoses, a novel class of α-glucosidase inhibitors Bioorg. Med. Chem. Lett. 2011, 21, 738-741
37. Trost, B. M.; Horne, D. B.; Woltering, M. J. Palladium-catalyzed DYKAT of butadiene monoepoxide: enantioselective total synthesis of (+)-DMDP, (-)-bulgecinine, and (+)-broussonetine G Chem.-Eur. J. 2006, 12, 6607-6620
38. Fu, G. C.; Zhou, J. S. Cross-couplings of unactivated secondary alkyl halides: room-temperature nickel-catalyzed Negishi reactions of alkyl bromides and iodides J. Am. Chem. Soc. 2003, 125, 14726-14727
39. 3) bonds by cyclization and cross-coupling reactions of iodoalkanes with alkyl zinc halides Angew. Chem., Int. Ed. 2007, 46, 8790-8795
40. Calveras, J.; Egido-Gabás, M.; Gómez, L.; Casas, J.; Parella, T.; Joglar, J.; Bujons, J.; Clapés, P. Dihydroxyacetone phosphate aldolase catalyzed synthesis of structurally diverse polyhydroxylated pyrrolidine derivatives and evaluation of their glycosidase inhibitory properties Chem.-Eur. J. 2009, 15, 7310-7328
41. Best, D.; Jenkinson, S. F.; Saville, A. W.; Alonzi, D. S.; Wormald, M. R.; Butters, T. D.; Norez, C.; Becq, F.; Bleriot, Y.; Adachi, I.; Kato, A.; Fleet, G. W. J. Cystic fibrosis and diabetes: isoLAB and isoDAB, enantiomeric carbon-branched pyrrolidine iminosugars Tetrahedron Lett. 2010, 51, 4170-4174
42. Scofield, A. M.; Fellows, L. E.; Nash, R. J.; Fleet, G. W. J. Inhibition of mammalian digestive disaccharides by polyhydroxy alkaloids Life Sci. 1986, 39, 645-650
43. Best, D.; Wang, C.; Weymouth-Wilson, A. C.; Clarkson, R. A.; Wilson, F. X.; Nash, R. J.; Miyauchi, S.; Kato, A.; Fleet, G. W. J. Looking glass inhibitors: scalable syntheses of DNJ, DMDP, and (3 R)-3-hydroxy- l -bulgecinine from d -glucuronolactone and of l -DNJ, l -DMDP, and (3 S)-3-hydroxy- d -bulgecinine from l -glucuronolactone. DMDP inhibits β-glucosidases and β-galactosidases whereas l -DMDP is a potent and specific inhibitor of α-glucosidases Tetrahedron: Asymmetry 2010, 21, 311-319
44. Ellgaard, L.; Molinari, M.; Helenius, A. Setting the standards: quality control in the secretory pathway Science 1999, 286, 1882-1888
45. Kopito, R. R. ER quality control: the cytoplasmic connection Cell 1997, 88, 427-430
46. Hammond, C.; Braakman, I.; Helenius, A. Role of N-linked oligosaccharide recognition, glucose trimming, and calnexin in glycoprotein folding and quality control Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 913-917
47. Hosokawa, N.; Wada, I.; Hasegawa, K.; Yorifuji, T.; Tremblay, L. O.; Herscovics, A.; Nagata, K. A novel ER α-mannosidase-like protein accelerates ER-associated degradation EMBO Rep. 2001, 2, 415-422
48. Hubbard, S. C.; Ivatt, R. J. Synthesis and processing of asparagines-linked oligosaccharides Annu. Rev. Biochem. 1981, 50, 555-583
49. Elbein, A. D. Inhibitors of the biosynthesis and processing of N -linked oligosaccharides CRC Crit. Rev. Biochem. 1984, 16, 21-49
50. Kopito, R. R. ER quality control: the cytoplasmic connection Cell 1997, 88, 427-430
51. Bonifacino, J. S.; Weissman, A. M. Ubiqitin and the control of protein in the secretory and the endoplasmic pathways Annu. Rev. Cell Dev. Biol. 1998, 14, 19-57
52. Elbein, A. D. Glycosidase inhibitors: inhibitors of N -linked oligosaccharide processing FASEB J. 1991, 5, 3055-3063
53. Asano, N.; Oseki, K.; Kizu, H; Matsui, K. Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases J. Med. Chem. 1994, 37, 3701-3706
54. Furukawa, J.; Shinohara, Y.; Kuramoto, H.; Miura, Y.; Shimaoka, H.; Kurogochi, M.; Nakano, M.; Nishimura, S. I. Comprehensive approach to structural and functional glycomics based on chemoselective glycoblotting and sequential tag conversion Anal. Chem. 2008, 80, 1094-1101
55. Dailey, G. Early and intensive therapy for management of hyperglycemia and cardiovascular risk factors in patients with type 2 diabetes Clin. Ther. 2011, 33, 665-678
56. Arakawa, M.; Ebato, C.; Mita, T.; Fujitani, Y.; Shimizu, T.; Watada, H.; Kawamori, R.; Hirose, T. Miglitol suppresses the postprandial increase in interleukin 6 and enhances active glucagon-like peptide 1 secretion in viscerally obese subjects Metabolism 2008, 57, 1299-1306
57. Aoki, K.; Kamiyama, H.; Yoshimura, K.; Shibuya, M.; Masuda, K.; Terauchi, Y. Miglitol administered before breakfast increased plasma active glucagon-like peptide-1 (GLP-1) levels after lunch in patients with type 2 diseases treated with sitagliptin Acta Diabetol. 2012, 49, 225-230
58. Aguilar-Moncayo, M.; Takai, T.; Higaki, K.; Mena-Barragán, T.; Hirano, Y.; Yura, K.; Li, L.; Yu, Y.; Ninomiya, H.; García-Moreno, M. I.; Ishii, S.; Sakakibara, Y.; Ohno, K.; Nanba, E.; Ortiz Mellet, C.; García Fernández, J. M.; Suzuki, Y. Tuning glycosidase inhibition through aglycone interactions: pharmacological chaperones for Fabry disease and GM1 gangliosidosis Chem. Commun. 2012, 48, 6514-6516
59. Kato, A.; Yamashita, Y.; Nakagawa, S.; Koike, Y.; Adachi, I.; Hollinshead, J.; Nas, R. J.; Ikeda, K.; Asano, N. 2,5-Dideoxy-2,5-imino- d -aritol as a new class of pharmacological chaperone for Fabry disease Bioorg. Med. Chem. 2010, 18, 3790-3794
60. Godin, G.; Compain, P.; Masson, G.; Martin, O. R. A general strategy for the practical synthesis of nojirimycin C -glycosides and analogues. Extension to the first reported example of an iminosugar 1-phosphonate J. Org. Chem. 2002, 67, 6960-6970
61. Godin, G.; Compain, P.; Martin, O. R. General access to iminosugar C -glycoside building blocks by means of cross-metathesis: a gateway to glycoconjugate mimetics Org. Lett. 2003, 5, 3269-3272
62. Fleet, G. W. J.; Nicholas, S. J.; Smith, P. W.; Evans, S. V.; Fellows, L. E.; Nash, R. J. Potent competitive inhibition of α-galactosidase and α-glucosidase activity by 1,4-dideoxy-1,4-iminopentitols: synthesis of 1,4-dideoxy-1,4-imino- d -lyxitol and of both enantiomer of 1,4-dideoxy-1,4- iminoarabinitol Tetrahedron Lett. 1985, 26, 3127-3130
63. Kessler, M.; Acuto, O.; Strelli, C.; Murer, H.; Semenza, G. A. A modified procedure for the rapid preparation of efficiently transporting vesicles from small intestinal brush border membranes. Their use in investigating some properties of d -glucose and choline transport systems Biochem. Biophys. Acta 1978, 506, 136-154
64. Cooper, C. A.; Gasteiger, E.; Packer, N. GlycoMod-a software tool for determining glycosylation compositions from mass spectrometric data Proteomics 2001, 1, 340-349
65. Sim, L.; Willemsma, C.; Mohan, S.; Naim, H. Y.; Pinto, B. M.; Rose, D. R. Structural basis for substrate selectivity in human maltase-glucoamylase and sucrase-isomaltase N -terminal domains J. Biol. Chem. 2010, 285, 17763-70
66. Laskowski, R. A.; MacArthur, M. W.; Moss, D. S.; Thornton, J. M. PROCHECK: a program to check the stereochemical quality of protein structures J. Appl. Crystallogr. 1993, 26, 283-291
67. Friesner, R. A.; Banks, J. L.; Murphy, R. B.; Halgren, T. A.; Klicic, J. J.; Mainz, D. T. Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy J. Med. Chem. 2004, 47, 1739-1749
68. Still, W. C.; Tempczyk, A.; Hawlely, R. C.; Hendrickson, T. Semianalytical treatment of solvation for molecular mechanics and dynamics J. Am. Chem. Soc. 1990, 112, 6127-6129
69. Sherman, W.; Day, T.; Jacobson, M. P.; Friesner, R. A.; Farid, R. Novel procedure for modeling ligand/receptor induced fit effects J. Med. Chem. 2006, 49, 534-553