Exploring the binding mode of semicarbazide-sensitive amine oxidase/VAP-1: Identification of novel substrates with insulin-like activity

Journal of Medicinal Chemistry

Volumn 47, Issue 20, 2004, Pages 4865-4874

  Marti, Luc ^a   Abella, Anna ^a   De La Cruz, Xavier ^b   García Vicente, Silvia ^a   Unzeta, Mercedes ^c   Carpéné, Christian ^d   Palacín, Manuel ^a   Testar, Xavier ^a   Orozco, Modesto ^a   Zorzano, Antonio ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

^c UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^d CHU RANGUEIL   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIMETHOXYBENZYLAMINE; 4 AMINOMETHYLBENZENESULFONAMIDE; AMIKACIN; AMINE; AMINE OXIDASE (COPPER CONTAINING); AROMATIC COMPOUND; BENZYLAMINE; BN 50125; BN 50192; BUTIROSIN; C NAPHTHALEN 1 YLMETHYLAMINE; CAPREOMYCIN; CEFORANIDE; DIBEKACIN; GLUCOSE; INSULIN; KANAMYCIN B; LIVIDOMYCIN; LYSINE; N ACETYLMURAMIC ACID; PARGYLINE; PD 0111700; PD 0119035; PD 119035; PD 125999; PHENYLALANINE; SEMICARBAZIDE; SULFONAMIDE; TYROSINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VANADATE SODIUM; VASCULAR ADHESION PROTEIN 1;

ADIPOCYTE; ANIMAL CELL; ARTICLE; CHEMICAL MODEL; CONTROLLED STUDY; DATA BASE; ENZYME ACTIVE SITE; ENZYME SUBSTRATE; ENZYME SUBSTRATE COMPLEX; GLUCOSE TRANSPORT; HUMAN; HUMAN CELL; INSULIN LIKE ACTIVITY; MOUSE; NONHUMAN; RAT; SEQUENCE HOMOLOGY;

EID: 4544262245     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0499211     Document Type: Article

References (38)

1. Raimondi, L.; Conforti, L.; Banchelli, G.; Ignesti, G.; Pirisino, R.; Buffoni, F. Histamine lipolytic activity and semicarbazide-sensitive amine oxidase (SSAO) of rat white adipose tissue (WAT). Biochem. Pharmacol. 1993, 46, 1369-1376.
2. Lyles, G. A. Substrate-specificity of mammalian tissue-bound semicarbazide-sensitive amine oxidase. Prog. Brain Res. 1995, 106, 293-303.
3. Lyles, G. A.; Bertie, K. H. Properties of a semicarbazide-sensitive amine oxidase in rat articular cartilage. Pharmacol. Toxicol. 1998, 60, 33.
4. Lizcano, J. M.; Balsa, D.; Tipton, K. F.; Unzeta, M. The oxidation of dopamine by the semicarbazide-sensitive amine oxidase (SSAO) from rat vas deferens. Biochem. Pharmacol. 1991, 41, 1107-1110.
5. Lizcano, J. M.; Fernandez, d. A.; Lyles, G. A.; Unzeta, M. Several aspects on the amine oxidation by semicarbazide-sensitive amine oxidase (SSAO) from bovine lung. J. Neural Transm. Suppl. 1994, 41, 415-420.
6. 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.
7. Bono, P.; Salmi, M.; Smith, D. J.; Jalkanen, S. Cloning and characterization of mouse vascular adhesion protein-1 reveals a novel molecule with enzymatic activity. J. Immunol. 1998, 160, 5563-5571.
8. Enrique-Tarancon, G.; Marti, L.; Morin, N.; Lizcano, J. M.; Unzeta, M.; Sevilla, L.; Camps, M.; Palacin, M.; Testar, X.; Carpene, C.; Zorzano, A. Role of semicarbazide-sensitive amine oxidase on glucose transport and GLUT4 recruitment to the cell surface in adipose cells. J. Biol. Chem. 1998, 273, 8025-8032.
9. Morris, N. J.; Ducret, A.; Aebersold, R.; Ross, S. A.; Keller, S. R.; Lienhard, G. E. Membrane amine oxidase cloning and identification as a major protein in the adipocyte plasma membrane. J. Biol. Chem. 1997, 272, 9388-9392.
10. Enrique-Tarancon, G.; Castan, I.; Morin, N.; Marti, L.; Abella, A.; Camps, M.; Casamitjana, R.; Palacin, M.; Testar, X.; Degerman, E.; Carpene, C.; Zorzano, A. Substrates of semicarbazide-sensitive amine oxidase co-operate with vanadate to stimulate tyrosine phosphorylation of insulin-receptor-substrate proteins, phosphoinositide 3-kinase activity and GLUT4 translocation in adipose cells. Biochem. J. 2000, 350 (Part 1), 171-180.
11. Marti, L.; Morin, N.; Enrique-Tarancon, G.; Prevot, D.; Lafontan, M.; Testar, X.; Zorzano, A.; Carpene, C. Tyramine and vanadate synergistically stimulate glucose transport in rat adipocytes by amine oxidase-dependent generation of hydrogen peroxide. J. Pharmacol. Exp. Ther. 1998, 285, 342-349.
12. Morin, N.; Lizcano, J. M.; Fontana, E.; Marti, L.; Smih, F.; Rouet, P.; Prevot, D.; Zorzano, A.; Unzeta, M.; Carpene, C. Semicarbazide-sensitive amine oxidase substrates stimulate glucose transport and inhibit lipolysis in human adipocytes. J. Pharmacol. Exp. Ther. 2001, 297, 563-572.
13. Morin, N.; Visentin, V.; Calise, D.; Marti, L.; Zorzano, A.; Testar, X.; Valet, P.; Fischer, Y.; Carpene, C. Tyramine stimulates glucose uptake in insulin-sensitive tissues in vitro and in vivo via its oxidation by amine oxidases. J. Pharmacol. Exp. Ther. 2002, 303, 1238-1247.
14. Fontana, E.; Boucher, J.; Marti, L.; Lizcano, J. M.; Testar, X.; Zorzano, A.; Carpene, C. Amine oxidase substrates mimic several of the insulin effects on adipocyte differentiation in 3T3 F442A cells. Biochem. J. 2001, 356, 769-777.
15. Abella, A.; Marti, L.; Camps, M.; Claret, M.; Fernandez-Alvarez, J.; Gomis, R.; Guma, A.; Viguerie, N.; Carpene, C.; Palacin, M.; Testar, X.; Zorzano, A. Semicarbazide-sensitive amine oxidase/vascular adhesion protein-1 activity exerts an antidiabetic action in Goto-Kakizaki rats. Diabetes 2003, 52, 1004-1013.
16. Marti, L.; Abella, A.; Carpene, C.; Palacin, M.; Testar, X.; Zorzano, A. Combined treatment with benzylamine and low dosages of vanadate enhances glucose tolerance and reduces hyperglycemia in streptozotocin-induced diabetic rats. Diabetes 2001, 50, 2061-2068.
17. Laskowski, R. A. Surfnet-A Program for Visualizing Molecular-Surfaces, Cavities, and Intermolecular Interactions. J. Mol. Graphics 1995, 13, 323-&.
18. Gelpi, J. L.; Kalko, S. G.; Barril, X.; Cirera, J.; de, L. C., X.; Luque, F. J.; Orozco, M. Classical molecular interaction potentials: improved setup procedure in molecular dynamics simulations of proteins. Proteins 2001, 45, 428-437.
19. Milne, G. W. A.; Miller, J. A. The NCI Drug Information System. 1. System Overview. J. Chem. Inf. Comput. Sci. 1986, 26, 154-159.
20. Precious, E.; Lyles, G. A. Properties of a semicarbazide-sensitive amine oxidase in human umbilical artery. J. Pharm. Pharmacol. 1988, 40, 627-633.
21. Precious, E.; Gunn, C. E.; Lyles, G. A. Deamination of methylamine by semicarbazide-sensitive amine oxidase in human umbilical artery and rat aorta. Biochem. Pharmacol. 1988, 37, 707-713.
22. Lyles, G. A.; Chalmers, J. The metabolism of aminoacetone to methylglyoxal by semicarbazide-sensitive amine oxidase in human umbilical artery. Biochem. Pharmacol. 1992, 43, 1409-1414.
23. Buffoni, F. Semicarbazide-sensitive amine oxidases: some biochemical properties and general considerations. Prog. Brain Res. 1995, 106, 323-331.
24. Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 1976, 72, 248-254.
25. Fowler, C. J.; Tipton, K. F. Concentration dependence of the oxidation of tyramine by the two forms of rat liver mitochondrial monoamine oxidase. Biochem. Pharmacol. 1981, 30, 3329-3332.
26. 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.
27. Sali, A.; Blundell, T. L. Comparative protein modelling by satisfaction of spatial restraints. J. Mol. Biol. 1993, 234, 779-815.
28. Li, R.; Klinman, J. P.; Mathews, F. S. Copper amine oxidase from Hansenula polymorpha: the crystal structure determined at 2.4 A resolution reveals the active conformation. Structure 1998, 6, 293-307.
29. Wilmot, C. M.; Murray, J. M.; Alton, G.; Parsons, M. R.; Convery, M. A.; Blakeley, V.; Corner, A. S.; Palcic, M. M.; Knowles, P. F.; McPherson, M. J.; Phillips, S. E. Catalytic mechanism of the quinoenzyme amine oxidase from Escherichia coli: exploring the reductive half-reaction. Biochemistry 1997, 36, 1608-1620.
30. 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.
31. Murzin, A. G.; Brenner, S. E.; Hubbard, T.; Chothia, C. SCOP: a structural classification of proteins database for the investigation of sequences and structures. J. Mol. Biol. 1995, 247, 536-540.
32. Bateman, A.; Birney, E.; Durbin, R.; Eddy, S. R.; Howe, K. L.; Sonnhammer, E. L. The Pfam protein families database. Nucleic Acids Res. 2000, 28, 263-266.
33. Mizuguchi, K.; Deane, C. M.; Blundell, T. L.; Overington, J. P. HOMSTRAD: a database of protein structure alignments for homologous families. Protein Sci. 1998, 7, 2469-2471.
34. Thompson, J. D.; Higgins, D. G.; Gibson, T. J. CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res. 1994, 22, 4673-4680.
35. Sippl, M. J. Recognition of errors in three-dimensional structures of proteins. Proteins 1993, 17, 355-362.
36. Melo, F. Feytmans, E. Assessing protein structures with a non-local atomic interaction energy. J. Mol. Biol. 1998, 277, 1141-1152.
37. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. A Second Generation Force Field for the Simulation of Proteins, Nucleic Acids, and Organic Molecules. J. Am. Chem. Soc. 1995, 117, 5179-5197.
38. Ewing, T. J.; Makino, S.; Skillman, A. G.; Kuntz, I. D. DOCK 4.0: search strategies for automated molecular docking of flexible molecule databases. J. Comput. Aided Mol. Des. 2001, 15, 411-428.