Novel pyridazinone inhibitors for vascular adhesion protein-1 (VAP-1): Old target-new inhibition mode

Journal of Medicinal Chemistry

Volumn 56, Issue 24, 2013, Pages 9837-9848

  Bligt Lindén, Eva ^a   Pihlavisto, Marjo ^b   Szatmári, István ^c   Otwinowski, Zbyszek ^d   Smith, David J ^b   Lázár, László ^c   Fülöp, Ferenc ^c   Salminen, Tiina A ^a  

^a ÅBO AKADEMI UNIVERSITY   (Finland)

^b Biotie Therapies Corp   (Finland)

^c UNIVERSITY OF SZEGED   (Hungary)

^d UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 [4 (4 METHYLPIPERAZIN 1 YL)PHENYLAMINO] 2 (4 CHLOROPHENYL) 6 (1H 1,2,4 TRIAZOL 3 YL) 3(2H) PYRIDAZINONE; 5 CYCLOHEXYLAMINO 2 PHENYL 6 (1H 1,2,4 TRIAZOL 3 YL) 3(2H) PYRIDAZINONE; 5 ISOPROPYLAMINO 2 PHENYL 6 (1H 1,2,4 TRIAZOL 3 YL) 3(2H) PYRIDAZINONE; AMINO ACID; PYRIDAZINONE DERIVATIVE; UNCLASSIFIED DRUG; VASCULAR ADHESION PROTEIN 1; VASCULAR ADHESION PROTEIN 1 INHIBITOR;

ANIMAL CELL; ARTICLE; BINDING SITE; CRYSTAL STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; HUMAN; NONHUMAN;

EID: 84891316808     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm401372d     Document Type: Article

References (59)

1. Palfreyman, M. G.; McDonald, I. A.; Bey, P.; Danzin, C.; Zreika, M.; Cremer, G. Haloallylamine inhibitors of MAO and SSAO and their therapeutic potential J. Neural Transm. Suppl. 1994, 41, 407-414
2. Floris, G. Copper Amine Oxidases: Structures, Catalytic Mechanisms, And Role in Pathophysiology; CRC Press: Boca Raton, FL, 2009; p 344.
3. Smith, D. J.; Salmi, M.; Bono, P.; Hellman, J.; Leu, T.; Jalkanen, S. Cloning of vascular adhesion protein 1 reveals a novel multifunctional adhesion molecule J. Exp. Med. 1998, 188, 17-27
4. Salmi, M.; Jalkanen, S. VAP-1: an adhesin and an enzyme Trends Immunol. 2001, 22, 211-216
5. Salmi, M.; Jalkanen, S. Ectoenzymes controlling leukocyte traffic Eur. J. Immunol. 2012, 42, 284-292
6. Dunkel, P.; Balogh, B.; Meleddu, R.; Maccioni, E.; Gyires, K.; Matyus, P. Semicarbazide-sensitive amine oxidase/vascular adhesion protein-1: a patent survey Expert Opin. Ther. Pat. 2011, 21, 1453-1471
7. Parsons, M. R.; Convery, M. A.; Wilmot, C. M.; Yadav, K. D.; Blakeley, V.; Corner, A. S.; Phillips, S. E.; McPherson, M. J.; Knowles, P. F. Crystal structure of a quinoenzyme: copper amine oxidase of Escherichia coli at 2 A resolution Structure 1995, 3, 1171-1184
8. Wilce, M. C.; Dooley, D. M.; Freeman, H. C.; Guss, J. M.; Matsunami, H.; McIntire, W. S.; Ruggiero, C. E.; Tanizawa, K.; Yamaguchi, H. Crystal structures of the copper-containing amine oxidase from Arthrobacter globiformis in the holo and apo forms: implications for the biogenesis of topaquinone Biochemistry 1997, 36, 16116-16133
9. Li, R.; Chen, L.; Cai, D.; Klinman, J. P.; Mathews, F. S. Crystallographic study of yeast copper amine oxidase Acta Crystallogr., Sect. D: Biol. Crystallogr. 1997, 53, 364-370
10. Duff, A. P.; Cohen, A. E.; Ellis, P. J.; Kuchar, J. A.; Langley, D. B.; Shepard, E. M.; Dooley, D. M.; Freeman, H. C.; Guss, J. M. The crystal structure of Pichia pastoris lysyl oxidase Biochemistry 2003, 42, 15148-15157
11. McGrath, A. P.; Mithieux, S. M.; Collyer, C. A.; Bakhuis, J. G.; van den Berg, M.; Sein, A.; Heinz, A.; Schmelzer, C.; Weiss, A. S.; Guss, J. M. Structure and activity of Aspergillus nidulans copper amine oxidase Biochemistry 2011, 50, 5718-5730
12. Freeman, H. C.; Guss, J. M.; Kumar, V.; McIntire, W. S.; Zubak, V. M. Purification, crystallization and preliminary X-ray crystal structure analysis of copper amine oxidase from Arthrobacter globoformis Acta Crystallogr., Sect. D: Biol. Crystallogr. 1996, 52, 197-198
13. Airenne, T. T.; Nymalm, Y.; Kidron, H.; Smith, D. J.; Pihlavisto, M.; Salmi, M.; Jalkanen, S.; Johnson, M. S.; Salminen, T. A. Crystal structure of the human vascular adhesion protein-1: unique structural features with functional implications Protein Sci. 2005, 14, 1964-1974
14. Jakobsson, E.; Nilsson, J.; Ogg, D.; Kleywegt, G. J. Structure of human semicarbazide-sensitive amine oxidase/vascular adhesion protein-1 Acta Crystallogr., Sect. D: Biol. Crystallogr. 2005, 61, 1550-1562
15. Ernberg, K.; McGrath, A. P.; Peat, T. S.; Adams, T. E.; Xiao, X.; Pham, T.; Newman, J.; McDonald, I. A.; Collyer, C. A.; Guss, J. M. A new crystal form of human vascular adhesion protein 1 Acta Crystallogr., Sect. F: Struct. Biol. Cryst. Commun. 2010, 66, 1572-1578
16. Lunelli, M.; Di Paolo, M. L.; Biadene, M.; Calderone, V.; Battistutta, R.; Scarpa, M.; Rigo, A.; Zanotti, G. Crystal structure of amine oxidase from bovine serum J. Mol. Biol. 2005, 346, 991-1004
17. Holt, A.; Smith, D. J.; Cendron, L.; Zanotti, G.; Rigo, A.; Di Paolo, M. L. Multiple binding sites for substrates and modulators of semicarbazide- sensitive amine oxidases: kinetic consequences Mol. Pharmacol. 2008, 73, 525-538
18. Elovaara, H.; Kidron, H.; Parkash, V.; Nymalm, Y.; Bligt, E.; Ollikka, P.; Smith, D. J.; Pihlavisto, M.; Salmi, M.; Jalkanen, S.; Salminen, T. A. Identification of two imidazole binding sites and key residues for substrate specificity in human primary amine oxidase AOC3 Biochemistry 2011, 50, 5507-5520
19. Emanuela, B.; Minarini, A.; Tumiatti, V.; Milelli, A.; Lunelli, M.; Pegoraro, M.; Rizzoli, V.; Di Paolo, M. L. Synthetic polyamines as potential amine oxidase inhibitors: a preliminary study Amino Acids 2012, 42, 913-928
20. Foot, J. S.; Deodhar, M.; Turner, C. I.; Yin, P.; van Dam, E. M.; Silva, D. G.; Olivieri, A.; Holt, A.; McDonald, I. A. The discovery and development of selective 3-fluoro-4-aryloxyallylamine inhibitors of the amine oxidase activity of semicarbazide-sensitive amine oxidase/vascular adhesion protein-1 (SSAO/VAP-1) Bioorg. Med. Chem. Lett. 2012, 22, 3935-3940
21. Yu, P. H.; Zuo, D. M.; Davis, B. A. Characterization of human serum and umbilical artery semicarbazide-sensitive amine oxidase (SSAO). Species heterogeneity and stereoisomeric specificity Biochem. Pharmacol. 1994, 47, 1055-1059
22. Marti, L.; Abella, A.; De La Cruz, X.; Garcia-Vicente, S.; Unzeta, M.; Carpene, C.; Palacin, M.; Testar, X.; Orozco, M.; Zorzano, A. Exploring the binding mode of semicarbazide-sensitive amine oxidase/VAP-1: identification of novel substrates with insulin-like activity J. Med. Chem. 2004, 47, 4865-4874
23. Schober, B. D.; Megyeri, G.; Kappe, T. Pyridazines with heteroatom substituents in position 3 and 5. 3. 2-Aryl-5-hydroxypyridazin-3(2 H)-ones as potential herbicides: Synthesis and some reactions J. Heterocycl. Chem 1989, 26, 169-176
24. Schober, B. D.; Megyeri, G.; Kappe, T. Pyridazines with heteroatom substituents in positions 3 and 5. 6. S-N reactions in position 5 of 2-aryl-5-hydroxypyridazin-3(2 H)-ones J. Heterocycl. Chem. 1990, 27, 471-477
25. Dajka-Halasz, B.; Monsieurs, K.; élias, O.; Károlyhá zy, L.; Tapolcsányi, P.; Maes, B. U. W.; Riedl, Z.; Hajós, G.; Dommisse, R. A.; Lemière, G. L. F.; Kosmrlj, J.; Mátyus, P. Synthesis of 5 H -pyridazino4,5- b ]indoles and their benzofurane analogues utilizing an intramolecular Heck-type reaction Tetrahedron 2004, 60, 2283
26. Lin, Y.; Lang, S. A.; Lovell, M. F.; Perkinson, N. A. New synthesis of 1,2,4-triazoles and 1,2,4-oxadiazoles J. Org. Chem. 1979, 44, 4160-4164
27. Marlow, A. L.; Wallace, E.; Seo, J.; Lyssikatos, J. P.; Yang, H.; Blake, J. Heterocyclic inhibitors of MEK and methods of use thereof. S20050256123, 2005.
28. Marlow, A. L.; Wallace, E.; Seo, J.; Lyssikatos, J. P.; Yang, H. W.; Blake, J.; Storey, R.; Booth, R. J.; Pittam, J. D.; Leonard, J.; Fielding, M. R. Heterocyclic inhibitors of MEK and methods of use thereof. WO2007044084, 2007.
29. Meegalla, S. K.; Wall, M. J.; Chen, J.; Wilson, K. J.; Ballentine, S. K.; DesJarlais, R. L.; Schubert, C.; Crysler, C. S.; Chen, Y.; Molloy, C. J.; Chaikin, M. A.; Manthey, C. L.; Player, M. R.; Tomczuk, B. E.; Illig, C. L. Structure-based optimization of a potent class of arylamide FMS inhibitors Bioorg. Med. Chem. Lett. 2008, 18, 3632-3637
30. Nurminen, E. M.; Pihlavisto, M.; Lazar, L.; Pentikainen, U.; Fulop, F.; Pentikainen, O. T. Novel hydrazine molecules as tools to understand the flexibility of vascular adhesion protein-1 ligand-binding site: toward more selective inhibitors J. Med. Chem. 2011, 54, 2143-2154
31. Bligt-Linden, E.; Arunachalam, R.; Parkash, V.; Salminen, T. A. Structural comparison of the active site channels in rodent and primate vascular adhesion protein-1 J. Neural Transm. 2013, 120, 947-950
32. Yraola, F.; Garcia-Vicente, S.; Fernandez-Recio, J.; Albericio, F.; Zorzano, A.; Marti, L.; Royo, M. New efficient substrates for semicarbazide-sensitive amine oxidase/VAP-1 enzyme: analysis by SARs and computational docking J. Med. Chem. 2006, 49, 6197-6208
33. Peltz, G. Can 'humanized' mice improve drug development in the 21st century? Trends Pharmacol. Sci. 2013, 34, 255-260
34. Misharin, A. V.; Haines, G. K., III; Rose, S.; Gierut, A. K.; Hotchkiss, R. S.; Perlman, H. Development of a new humanized mouse model to study acute inflammatory arthritis J. Transl. Med. 2012, 10, 190
35. Imam, S.; Elagin, R. B.; Jaume, J. C. Diabetes-associated dry eye syndrome in a new humanized transgenic model of type 1 diabetes Mol. Vis. 2013, 19, 1259-1267
36. Maula, S. M.; Salminen, T.; Kaitaniemi, S.; Nymalm, Y.; Smith, D. J.; Jalkanen, S. Carbohydrates located on the top of the "cap" contribute to the adhesive and enzymatic functions of vascular adhesion protein-1 Eur. J. Immunol. 2005, 35, 2718-2727
37. Nurminen, E. M.; Pihlavisto, M.; Lazar, L.; Szakonyi, Z.; Pentikainen, U.; Fulop, F.; Pentikainen, O. T. Synthesis, in vitro activity, and three-dimensional quantitative structure-activity relationship of novel hydrazine inhibitors of human vascular adhesion protein-1 J. Med. Chem. 2010, 53, 6301-6315
38. Inoue, T.; Morita, M.; Tojo, T.; Yoshihara, K.; Nagashima, A.; Moritomo, A.; Ohkubo, M.; Miyake, H. Synthesis and SAR study of new thiazole derivatives as vascular adhesion protein-1 (VAP-1) inhibitors for the treatment of diabetic macular edema Bioorg. Med. Chem. 2013, 21, 1219-1233
39. Inoue, T.; Morita, M.; Tojo, T.; Nagashima, A.; Moritomo, A.; Imai, K.; Miyake, H. Synthesis and SAR study of new thiazole derivatives as vascular adhesion protein-1 (VAP-1) inhibitors for the treatment of diabetic macular edema: part 2 Bioorg. Med. Chem. 2013, 21, 2478-2494
40. McGrath, A. P.; Hilmer, K. M.; Collyer, C. A.; Shepard, E. M.; Elmore, B. O.; Brown, D. E.; Dooley, D. M.; Guss, J. M. Structure and inhibition of human diamine oxidase Biochemistry 2009, 48, 9810-9822
41. Holt, A.; Sharman, D. F.; Baker, G. B.; Palcic, M. M. A continuous spectrophotometric assay for monoamine oxidase and related enzymes in tissue homogenates Anal. Biochem. 1997, 244, 384-392
42. Nymalm, Y.; Kidron, H.; Soderholm, A.; Viitanen, L.; Kaukonen, K.; Pihlavisto, M.; Smith, D.; Veromaa, T.; Airenne, T. T.; Johnson, M. S.; Salminen, T. A. Crystallization and preliminary X-ray analysis of the human vascular adhesion protein-1 Acta Crystallogr., Sect. D: Biol. Crystallogr. 2003, 59, 1288-1290
43. Otwinowski, Z.; Minor, W. Processing of X-ray diffraction data collected in the oscillation mode Method Enzymol. 1997, 276, 307-326
44. Dodson, E. J.; Winn, M.; Ralph, A. Collaborative Computational Project, number 4: providing programs for protein crystallography Methods Enzymol. 1997, 277, 620-633
45. Minor, W.; Cymborowski, M.; Otwinowski, Z.; Chruszcz, M. HKL-3000: the integration of data reduction and structure solution-from diffraction images to an initial model in minutes Acta Crystallogr., Sect. D: Biol. Crystallogr. 2006, 62, 859-866
46. Borek, D.; Minor, W.; Otwinowski, Z. Measurement errors and their consequences in protein crystallography Acta Crystallogr., Sect. D: Biol. Crystallogr. 2003, 59, 2031-2038
47. Otwinowski, Z.; Borek, D.; Majewski, W.; Minor, W. Multiparametric scaling of diffraction intensities Acta Crystallogr., Sect. A: Found. Crystallogr. 2003, 59, 228-234
48. Borek, D.; Cymborowski, M.; Machius, M.; Minor, W.; Otwinowski, Z. Diffraction data analysis in the presence of radiation damage Acta Crystallogr., Sect. D: Biol. Crystallogr. 2010, 66, 426-436
49. Borek, D.; Ginell, S. L.; Cymborowski, M.; Minor, W.; Otwinowski, Z. The many faces of radiation-induced changes J. Synchrotron Radiat. 2007, 14, 24-33
50. Borek, D.; Dauter, Z.; Otwinowski, Z. Identification of patterns in diffraction intensities affected by radiation exposure J. Synchrotron Radiat. 2013, 20, 37-48
51. Murshudov, G. N.; Vagin, A. A.; Dodson, E. J. Refinement of macromolecular structures by the maximum-likelihood method Acta Crystallogr., Sect. D: Biol. Crystallogr. 1997, 53, 240-255
52. Emsley, P.; Cowtan, K. Coot: model-building tools for molecular graphics Acta Crystallogr., Sect. D: Biol. Crystallogr. 2004, 60, 2126-2132
53. Schuttelkopf, A. W.; van Aalten, D. M. PRODRG: a tool for high-throughput crystallography of protein-ligand complexes Acta Crystallogr., Sect. D: Biol. Crystallogr. 2004, 60, 1355-1363
54. Davis, I. W.; Leaver-Fay, A.; Chen, V. B.; Block, J. N.; Kapral, G. J.; Wang, X.; Murray, L. W.; Arendall, W. B., III; Snoeyink, J.; Richardson, J. S.; Richardson, D. C. MolProbity: all-atom contacts and structure validation for proteins and nucleic acids Nucleic Acids Res. 2007, 35, W375-W383
55. Kleywegt, G. J. Unpublished program. Uppsala University: Uppsala, Sweden, 1992-2001.
56. Kleywegt, G. J.; Zou, J. Y.; Kjeldgaard, M.; Jones, T. A. Model Building and Computer Graphics. In International Tables for Crystallography, Vol. F: Crystallography of Biological Macromolecules; Rossman, M. G.; Arnold, E., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2001; pp 353-356, 366-367.
57. Maestro, v. 9.3; Schrödinger, LLC: New York, 2012.
58. Vagin, A. A.; Richelle, J.; Wodak, S. J. SFCHECK: a unified set of procedure for evaluating the quality of macromolecular structure-factor data and their agreement with atomic model Acta Cryst. 1999, D55, 191-205
59. DeLano, W. L. The PyMoL Molecular Graphics Systems. Scientific LLC: Palo Alto, CA, 2008.