Design and synthesis of highly potent and selective (2-arylcarbamoyl- phenoxy)-acetic acid inhibitors of aldose reductase for treatment of chronic diabetic complications

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 21, 2004, Pages 5661-5675

  Van Zandt, Michael C ^a   Sibley, Evelyn O ^a   McCann, Erin E ^a   Combs, Kerry J ^a   Flam, Brenda ^a   Sawicki, Diane R ^a   Sabetta, Al ^a   Carrington, Anne ^a   Sredy, Janet ^a   Howard, Eduardo ^b   Mitschler, Andre ^b   Podjarny, Alberto D ^b  

^a The Institute for Diabetes Discovery   (United States)

^b INSTITUT DE GÉNÉTIQUE ET DE BIOLOGIE MOLÉCULAIRE ET CELLULAIRE   (France)

Author keywords

Aldehyde reductase; Aldose reductase; Complications; Diabetes

Indexed keywords

ALDOSE REDUCTASE INHIBITOR; ANTIDIABETIC AGENT;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BINDING AFFINITY; CHEMICAL REACTION; CONTROLLED STUDY; DOSE RESPONSE; DRUG DESIGN; DRUG DOSE REGIMEN; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGEN BOND; IC 50; MOUSE; NONHUMAN; PHARMACOPHORE; STREPTOZOCIN DIABETES;

ACETIC ACID; ALDEHYDE REDUCTASE; ANIMALS; CHRONIC DISEASE; DIABETES MELLITUS, EXPERIMENTAL; DRUG DESIGN; ENZYME INHIBITORS; MALE; RATS; RATS, SPRAGUE-DAWLEY; SORBITOL;

EID: 4644301086     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.07.062     Document Type: Article

References (44)

1. American Diabetes Association's homepage. http://www.diabetes.org
2. The Diabetes Control and Complications Trial Research Group. The effect of intensive treatment of diabetes on the development and progression of long-term complications in insulin-dependent diabetes mellitus. N. Engl. J. Med. 1993, 329, 977-986
3. The United Kingdom Prospective Diabetes Study Group. Intensive blood-glucose control with sulfonyl-ureas or insulin compared with conventional treatment and risk of complications in patients with Type 2 diabetes (UKPDS33). Lancet 1998, 352, 837-853
4. J.C. Pickup G. Williams Textbook of Diabetes Vol. 1 1997 Blackwell Science United Kingdom Chapter 42
5. J.R. Williamson Hyperglycemic pseudohypoxia and diabetic complications Diabetes 42 1993 801 813
6. A. Lee, S.K. Chung, and S.S. Chung Demonstration that polyol accumulation is responsible for diabetic cataract by use of transgenic mice expressing the aldose reductase gene in the lens Proc. Natl. Acad. Sci. U.S.A. 92 1995 2780 2784
7. P.J. Oates, and B.L. Mylari Aldose reductase inhibitors: therapeutic implications for diabetic complications Expert Opin. Inv. Drug. 8 1999 1 15
8. Y.-L. Kao, K. Donahue, A. Chan, J. Knight, and M. Silink A novel polymorphism in the aldose reductase gene promoter region is strongly associated with diabetic retinopathy in adolescents with Type I diabetes Diabetes 48 1999 1338 1340
9. A. Heesom, M. Hibberd, A. Millward, and A. Demaine Polymorphism in the 5′-end of the aldose reductase gene is strongly associated with the development of diabetic nephropathy in Type I diabetes Diabetes 46 1997 287 291
10. D. Moczulski The role of aldose reductase gene in the susceptibility to diabetic nephropathy in Type II (non-insulin-dependent) diabetes mellitus Diabetologia 42 1999 94 97
11. M. Shinoda, S. Mori, S. Shintani, S. Ishikura, and A. Hara Inhibition of human aldehyde reductase by drugs for testing the function of liver and kidney Biol. Pharm. Bull. 22 1999 741 744
12. K. Suzuki, Y.H. Koh, H. Mizuno, R. Hamaoka, and N. Taniguchi Overexpression of aldehyde reductase protects PC12 cells from the cytotoxicity of methylglyoxal or 3-deoxyglucosone J. Biochem. 123 1998 353 357
13. M. Takahashi, J. Fujii, T. Teshima, K. Suzuki, T. Shiba, and N. Taniguchi Identity of a major 3-deoxyglucosone-reducing enzyme with aldehyde reductase in rat liver established by amino acid sequencing and cDNA expression Gene 127 1993 249 253
14. T. Kanazu, M. Shinoda, T. Nakayama, Y. Deyashiki, A. Hara, and H. Sawada Aldehyde reductase is a major protein associated with 3-deoxyglucosone reductase activity in rat, pig and human livers Biochem. J. 279 1991 903 906
15. Y. Hamada, N. Araki, N. Koh, J. Nakamura, S. Horiuchi, and N. Hotta Rapid formation of advanced glycation end-products by intermediate metabolites of glycolytic pathway and polyol pathway Biochem. Biophys. Res. Commun. 228 1996 539 543
16. T. Oya, N. Hattori, Y. Mizuno, S. Miyata, S. Maeda, T. Osawa, and K. Uchida Methylglyoxal modification of protein J. Biol. Chem. 274 1999 18492 18502
17. F. Cavalot, G. Anfossi, I. Russo, E. Mularoni, P. Massucco, L. Mattiello, S. Burzacca, A. Hahn, and M. Trovati Nonenzymatic glycation of fibronectin impairs adhesive and proliferative properties of human vascular smooth muscle cells Metabolism 45 1996 285 292
18. M. Fu, K. Wells-Knecht, J. Blackledge, T. Lyons, S. Thorpe, and J. Baynes Glycation, glycoidation, and cross-linking of collagen by glucose Diabetes 43 1994 676 683
19. T.G. Flynn, N.C. Green, M.B. Bhatia, and El-Kabbani Structure and mechanism of aldehyde reductase Weiner Enzymology and Molecular Biology of Carbonyl Metabolism 5 1995 Plenum New York 193 201 Chapter 25
20. D.H.T. Harrison, K.M. Bohren, G.A. Petsko, D. Ringe, and K.H. Gabbay The alrestatin double-decker: binding of two inhibitor molecules to human aldose reductase reveals a new specificity determinant Biochemistry 36 1997 16134 16140
21. Umezu, K. Preparation of 4-fluorosalicylic acids from difluorobenzoic acids in polar aprotic solvents. Japanese patent JP 96-193878
22. J. Wrobel, J. Millen, J. Sredy, A. Dietrich, B. Gorham, M. Malamas, J. Kelly, J. Bauman, M. Harrison, L. Jones, C. Guinosso, and K. Sestanj Synthesis of tolrestat analogues containing additional substituents in the ring and their evaluation as aldose reductase inhibitors. Identification of poten, orally active 2-fluoro derivatives J. Med. Chem. 34 1991 2504 2520
23. J.L. Hartwell o-Chlorobromobenzene Org. Syn. (Collective Volume III) 1955 185
24. J. Wolfe, and S. Büchwald Scope and limitations of the Pd/BINAP-catalyzed amination of aryl bromides J. Org. Chem. 65 2000 1144 1157
25. A. Urzhumtsev, F. Těte-Favier, A. Mitschler, J. Barbanton, P. Barth, L. Urzhumtseva, J.-F. Biellmann, A.D. Podjarny, and D.A. Moras 'Specificity' pocket inferred from the crystal structures of the complexes of aldose reductase with the pharmaceutically important inhibitors tolrestat and sorbinil Structure 5 1997 601 612
26. O. El-Kabbani, D.K. Wilson, J.M. Petrash, and F.A. Quiocho Structural features of the aldose reductase and aldehyde reductase inhibitor-binding sites Mol. Vis. 4 1998 19 25
27. K.J. Rees-Milton, Z. Jia, N.C. Green, M. Bhatia, O. El-Kabbani, and T.G. Flynn Aldehyde reductase: the role of C-terminal residues in defining substrate and cofactor specificities Arch. Biochem. Biophys. 355 1998 137 144
28. O. El-Kabbani, D.A. Carper, M.H. McGowan, Y. Devedjiev, K.J. Rees-Milton, and T.G. Flynn Studies on the inhibitor-binding site of porcine aldehyde reductase: crystal structure of the holoenzyme-inhibitor ternary complex Proteins 29 1997 186 192
29. E. Howard, R. Sanishvili, R. Cachau, A. Mitschler, B. Chevrier, P. Barth, V. Lamour, M.C. Van Zandt, E. Sibley, C. Bon, D. Moras, T.R. Schneider, A. Joachimiak, and A. Podjarny Ultrahigh resolution drug design I: details of interactions in human aldose reductase-inhibitor complex at 0.66 â. Proteins: Struct., Funct., Bioinformatics 55 2004 792 804
30. T. Kotani, Y. Nagaki, A. Ishii, Y. Konishi, H. Yago, S. Suehiro, N. Okukado, and K. Okamoto Highly selective aldose reductase inhibitors. 3. Structural diversity of 3-(arylmethyl)-2,4,5-trioxoimidazolidine-1-acetic acids J. Med. Chem. 40 1997
31. M. Malamas, T. Holman, and J. Millen Novel spirosuccinimide aldose reductase inhibitors derived from isoquinoline-1,3-diones: 2-[(4-bromo-2- fluorophenyl)methyl]-6-fluorospiro[isoquinoline-4(1H),3′-pyrrolidine]-1, 2′,3,5′(2H)-tetrone and congeners J. Med. Chem. 37 1994 2043 2058
32. B. Mylar, E. Larson, T. Beyer, W. Zembrowski, C. Aldinger, M. Dee, T. Siegel, and D. Singleton Novel, potent aldose reductase inhibitors: 3,4-dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl]methyl] -1-phthalazine-acetic acid (zopolrestat and congeners) J. Med. Chem. 34 1991 108 122
33. Jones, M.; Gunn, D.; Jones, J.; Van Zandt, M. U.S. Patent 6,214,991, 2001
34. Tomoji, A.; Nishio, T.; Hosono, H.; Nakamura, Y.; Matsui, T.; Ishikawa, H. U.S. Patent 5,543,420, 1994
35. S. Hayman, and J.H. Kinoshita J. Biol. Chem. 240 1965 877 880
36. O.A. Barski, K.H. Gabbay, C.E. Grimshaw, and K.M. Bohren Mechanism of human aldehyde reductase: characterization of the active site pocket Biochemistry 34 1995 11264 11275
37. D. Stribling, D.J. Mirrlees, H.E. Harrison, and D.C.N. Earl Properties of ICI 128,436 a novel aldose reductase inhibitor, and its effects on diabetic complications in the rat Metabolism 4 1985 336 344
38. N. Ashizawa, M. Yoshida, Y. Sugiyama, N. Akaike, S. Ohbayashi, T. Aotsuka, N. Abe, K. Fukushima, and A. Matsuura Effects of a novel potent aldose reductase inhibitor, GP-1447, on aldose reductase activity in vitro and on diabetic neuropathy and cataract formation in rats Jpn. J. Pharmacol. 73 1997 133 144
39. +/NADPH and alrestatin-like inhibitors Biochemistry 33 1994 7157 7165
40. H.U. Bergmeyer, W. Gruber, and I. Gutmann 2nd ed. H.U. Bergmeyer Methods of Enzymatic Analysis Vol. 3 1974 Weinheim and Academic New York, London 1323 1330
41. J.I. Malone, G. Knox, S. Benford, and T.A. Tedesco Red cell sorbitol. An indicator of diabetic control Diabetes 29 1980 861 864
42. Z. Otwinowski, and W. Minor C.W. Carter Jr. R.M. Sweet Methods in Enzymology, Macromolecular Crystallography, part A Vol. 276 1997 Academic 307 326
43. T.A. Jones, J.Y. Zou, S.W. Cowan, and M.O. Kjeldgaard Acta Cryst. A47 1991 110 119
44. Brunger, A. T. Yale University Press: New Haven, CT, USA, 1992