SSAO substrates exhibiting insulin-like effects in adipocytes as a promising treatment option for metabolic disorders

Future Medicinal Chemistry

Volumn 2, Issue 12, 2010, Pages 1735-1749

  Mercader, Josep ^a   Iffiú Soltesz, Zsuzsa ^a   Brenachot, Xavier ^a   Földi, Ágota ^b   Dunkel, Petra ^b   Balogh, Balázs ^b   Attané, Camille ^a   Valet, Philippe ^a   Mátyus, Péter ^b   Carpéné, Christian ^a  

^a CHU RANGUEIL   (France)

^b SEMMELWEIS UNIVERSITY   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINOBENZAMIDE; ADIPOCYTOKINE; AMINE OXIDASE (COPPER CONTAINING); AMINE OXIDASE (FLAVIN CONTAINING); AMINOGUANIDINE; APELIN; BENZYLAMINE; BENZYLAMINE DERIVATIVE; CADAVERINE; GLUCOSAMINE; HYDROGEN PEROXIDE; INSULIN; METHYLAMINE; N,N DIMETHYL 2 (2 AMINO 4 METHYLPHENYLTHIO)BENZYLAMINE; PARGYLINE; PROTEIN KINASE B; SEMICARBAZIDE; SEROTONIN; SPERMINE; TRIACYLGLYCEROL; TYRAMINE; UNCLASSIFIED DRUG; VANADATE SODIUM;

ADIPOCYTE; ADIPOGENESIS; ANIMAL CELL; ANIMAL CELL CULTURE; ARTICLE; DRUG ACTIVITY; DRUG EFFECT; DRUG MECHANISM; DRUG STRUCTURE; ENZYME ACTIVITY; GENE EXPRESSION; GLUCOSE TRANSPORT; HUMAN; HUMAN CELL; HUMAN TISSUE; IN VITRO STUDY; IN VIVO STUDY; INSULIN RESISTANCE; LIPOLYSIS; METABOLIC DISORDER; MOUSE; NONHUMAN; POLYMERASE CHAIN REACTION; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN PHOSPHORYLATION;

3T3 CELLS; ADIPOCYTES; AMINE OXIDASE (COPPER-CONTAINING); ANIMALS; BENZYLAMINES; GENE EXPRESSION REGULATION; GLUCOSE; HUMANS; HYDROGEN PEROXIDE; INSULIN; INSULIN RESISTANCE; INTERCELLULAR SIGNALING PEPTIDES AND PROTEINS; METABOLIC DISEASES; MICE; SEMICARBAZIDES;

EID: 78650182603     PISSN: 17568919     EISSN: None     Source Type: Journal    
DOI: 10.4155/fmc.10.260     Document Type: Article

References (80)

1. Medda R, Bellelli A, Pec P, Federico R, Cona A, Floris G. Copper amine oxidases from plants. In: Copper Amine Oxidases: Structures, Catalytic Mechanisms and Role in Pathophysiology. Floris G, Mondovì B (Eds). CRC Press, FL, USA 39-50 (2009).
2. Pietrangeli P, Morpurgo L, Mondovì B, Di Paolo ML, Rigo A. Soluble Copper amine oxidases from mammals. In: Copper Amine Oxidases: Structures, Catalytic Mechanisms and Role in Pathophysiology. Floris G, Mondovì B (Eds). CRC Press, FL, USA 51-68 (2009).
3. Boyce S, Tipton KF, O'Sullivan MI et al. Nomenclature and potential functions of copper amine oxidases. In: Copper Amine Oxidases: Structures, Catalytic Mechanisms and Role in Pathophysiology. Floris G & Mondovì B (Eds). CRC Press, FL, USA 5-18 (2009).
4. Boomsma F, Derkx FH, van den Meiracker AH, Man in't Veld AJ, Schalekamp MA. Plasma semicarbazide-sensitive amine oxidase activity is elevated in diabetes mellitus and correlates with glycosylated hemoglobin. Clin. Sci. (Lond.) 88, 675-679 (1995).
5. Boomsma F, van den Meiracker AH, Winkel S et al. Circulating semicarbazide-sensitive amine oxidase is raised both in Type I (insulin-dependent), in Type II (non-insulindependent) diabetes mellitus and even in childhood Type I diabetes at first clinical diagnosis. Diabetologia 42, 233-237 (1999).
6. Garpenstrand H, Ekblom J, Backlund LB, Oreland L, Rosenqvist U. Elevated plasma semicarbazide-sensitive amine oxidase (SSAO) activity in Type 2 diabetes mellitus complicated by retinopathy. Diabet. Med. 16, 514-521 (1999).
7. Meszaros Z, Szombathy T, Raimondi L, Karadi I, Romics L, Magyar K. Elevated serum semicarbazide-sensitive amine oxidase activity in non-insulin-dependent diabetes mellitus: Correlation with body mass index and serum triglyceride. Metabolism 48, 113-117 (1999).
8. Boomsma F, Pedersen-Bjergaard U, Agerholm-Larsen B et al. Association between plasma activities of semicarbazide-sensitive amine oxidase and angiotensin-converting enzyme in patients with Type 1 diabetes mellitus. Diabetologia 48, 1002-1007 (2005).
9. Gokturk C, Nordquist J, Sugimoto H, Forsberg-Nilsson K, Nilsson J, Oreland L. Semicarbazide-sensitive amine oxidase in transgenic mice with diabetes. Biochem. Biophys. Res. Commun. 325, 1013-1020 (2004).
10. Visentin V, Bour S, Boucher J et al. Glucose handling in streptozotocin-induced diabetic rats is improved by tyramine but not by the amine oxidase inhibitor semicarbazide. Eur. J. Pharmacol. 522, 139-146 (2005).
11. Somfai GM, Knippel B, Ruzicska E et al. Soluble semicarbazide-sensitive amine oxidase (SSAO) activity is related to oxidative stress and subchronic inflammation in streptozotocin-induced diabetic rats. Neurochem. Int. 48, 746-752 (2006).
12. Cioni L, De Siena G, Ghelardini C et al. Activity and expression of semicarbazidesensitive benzylamine oxidase in a rodent model of diabetes: Interactive effects with methylamine and a-aminoguanidine. Eur. J. Pharmacol. 529, 179-187 (2006).
13. Ekblom J. Potential therapeutic value of drugs inhibiting semicarbazide-sensitive amine oxidase: Vascular cytoprotection in diabetes mellitus. Pharmacol. Res. 37, 87-92 (1998).
14. Mátyus P, Dajka-Halász B, Földi A, Haider N, Barlocco D, Magyar K. Semicarbazidesensitive amine oxidase: Current status and perspectives. Curr. Med. Chem. 11, 1285-1298 (2004).
15. Yu P, Zuo D. Aminoguanidine inhibits semicarbazide-sensitive amine oxidase activity: Implications for advanced glycation and diabetic complications. Diabetologia 40, 1243-1250 (1997).
16. Gubisne-Haberlé D, Hill W, Kazachkov M, Richardson JS, Yu PH. Protein cross-linkage induced by formaldehyde derived from semicarbazide- sensitive amine oxidasemediated deamination of methylamine. J. Pharmacol. Exp. Ther. 310, 1125-1132 (2004).
17. Yu PH, Wang M, Fan H, Deng Y, Gubisne- Haberlé D. Involvement of SSAO-mediated deamination in adipose glucose transport and weight gain in obese diabetic KKAy mice. Am. J. Physiol. Endocrinol. Metab. 286, E634-E641 (2004).
18. Prévot D, Soltesz Z, Abello V et al. Prolonged treatment with aminoguanidine strongly inhibits adipocyte semicarbazide-sensitive amine oxidase and slightly reduces fat deposition in obese Zucker rats. Pharmacol. Res. 56, 70-79 (2007).
19. Masini E, Raimondi L. Pharmacological applications of copper amine oxidases. In: Copper Amine Oxidases: Structures, Catalytic Mechanisms and Role in Pathophysiology. Floris G, Mondovì B (Eds). CRC Press, FL, USA 239-252 (2009).
20. Kazachkov M, Chen K, Babiy S, Yu PH. Evidence for in vivo scavenging by aminoguanidine of formaldehyde produced via SSAO-mediated deamination. J. Pharmacol. Exp. Ther. 322, 1201-1207 (2007).
21. Yu PH, Wang M, Deng YL, Fan H, Shira-Bock L. Involvement of semicarbazidesensitive amine oxidase-mediated deamination in atherogenesis in KKAy diabetic mice fed with high cholesterol diet. Diabetologia 45, 1255-1262 (2002).
22. Mercier N, El Hadri K, Osborne-Pellegrin M et al. Modifications of arterial phenotype in response to amine oxidase inhibition by semicarbazide. Hypertension 50, 234-241 (2007).
23. Mercier N, Kakou A, Challande P, Lacolley P, Osborne-Pellegrin M. Comparison of the effects of semicarbazide and b-aminopropionitrile on the arterial extracellular matrix in the Brown Norway rat. Toxicol. Appl. Pharmacol. 239, 258-267 (2009).
24. Carpéné C, Bour S, Visentin V et al. Amine oxidase substrates for impaired glucose tolerance correction. J. Physiol. Biochem. 61, 405-420 (2005).
25. Moldes M, Fève B, Pairault J. Molecular cloning of a major mRNA species in murine 3T3 adipocyte lineage. Differentiationdependent expression, regulation, and identification as semicarbazide-sensitive amine oxidase. J. Biol. Chem. 274, 9515-9523. (1999).
26. Bour S, Daviaud D, Grès S et al. Adipogenesis-related increase of semicarbazide-sensitive amine oxidase and monoamine oxidase in human adipocytes. Biochimie 89, 916-925 (2007).
27. Morris NJ, Ducret A, Aebersold R, Ross SA, Keller SR, Lienhard GE. Membrane amine oxidase cloning and identification as a major protein in the adipocyte plasma membrane. J. Biol. Chem. 272, 9388-9392 (1997).
28. Morin N, Lizcano JM, Fontana E et al. Semicarbazide-sensitive amine oxidase substrates stimulate glucose transport and inhibit lipolysis in human adipocytes. J. Pharmacol. Exp. Ther. 297, 563-572 (2001).
29. Zorzano A, Abella A, Marti L, Carpéné C, Palacin M, Testar X. Semicarbazide-sensitive amine oxidase activity exerts insulin-like effects on glucose metabolism and insulinsignaling pathways in adipose cells. Biochim. Biophys. Acta 1647, 3-9 (2003).
30. Enrique-Tarancon G, Castan I, Morin N et al. Substrates of semicarbazide-sensitive amine oxidase cooperate with vanadate to stimulate tyrosine phosphorylation of IRS proteins, phosphatidylinositol 3-kinase activity and GLUT4 translocation in adipose cells. Biochem. J. 350, 171-180 (2000).
31. Lu B, Ennis D, Lai R et al. Enhanced sensitivity of insulin-resistant adipocytes to vanadate is associated with oxidative stress and decreased reduction of vanadate (±5) to vanadyl (±4). J. Biol. Chem. 276, 35589-35598 (2001).
32. Huyer G, Liu S, Kelly J et al. Mechanism of inhibition of protein-tyrosine phosphatases by vanadate and pervanadate. J. Biol. Chem. 272, 843-851 (1997).
33. Shisheva A, Shechter Y. Mechanism of pervanadate stimulation and potentiation of insulin-activated glucose transport in rat adipocytes: Dissociation from vanadate effect. Endocrinology 133, 1562-1568 (1993).
34. Nolte LA, Han DH, Hansen PA, Hucker KA, Holloszy JO. A peroxovanadium compound stimulates muscle glucose transport as powerfully as insulin and contractions combined. Diabetes 52, 1918-1925 (2003).
35. Abella A, Marti L, Camps M et al. Semicarbazide-sensitive amine oxidase/ vascular adhesion protein-1 activity exerts an antidiabetic action in Goto-Kakizaki rats. Diabetes 52, 1004-1013 (2003).
36. Marti L, Abella A, Carpéné C, Palacin M, Testar X, Zorzano A. Combined treatment with benzylamine and low dosages of vanadate enhances glucose tolerance and reduces hyperglycemia en streptozotocin-induced diabetic rats. Diabetes 50, 2061-2068 (2001).
37. Nilsson J, Degerman E, Haukka M et al. Bis- and tris(pyridyl)amine- oxidovanadium complexes: Characteristics and insulinmimetic potential. Dalton Trans. 38, 7902-7911 (2009).
38. Yraola F, Garcia-Vicente S, Marti L, Albericio F, Zorzano A, Royo M. Understanding the mechanism of action of the novel SSAO substrate (C7NH10)6(V10O28).2H2O, a prodrug of peroxovanadate insulin mimetics. Chem. Biol.Drug Des. 69, 423-428 (2007).
39. Zorzano A, Palacín M, Marti L, García- Vicente S. Arylalkylamine vanadium salts as new anti-diabetic compounds. J. Inorg. Biochem. 103, 559-566 (2009).
40. Soltesz Z, Tabi T, Halasz AS et al. Studies on the insulinomimetic effects of benzylamine, exogenous substrate of semicarbazide-sensitive amine oxidase enzyme, in streptozotocin induced diabetic rtas. J. Neural Transm. 114, 851-855 (2007).
41. Iffiú-Soltész Z, Prévot D, Grès S et al. Influence of benzylamine acute and chronic administration of benzylamine on glucose tolerance in diabetic and obese mice fed on very high-fat diet. J. Physiol. Biochem. 63, 305-316 (2007).
42. Iffiú-Soltész Z, Wanecq E, Lomba A et al. Chronic benzylamine administration in the drinking water improves glucose tolerance, reduces body weight gain and circulating cholesterol in high-fat diet-fed mice. Pharmacol. Res. 61, 355-363 (2010).
43. El Hadri K, Moldes M, Mercier N, Andreani M, Pairault J, Fève B. Semicarbazide-sensitive amine oxidase in vascular smooth muscle cells: Differentiation-dependent expression and role in glucose uptake. Arterioscler. Thromb. Vasc. Biol. 22, 89-94 (2002).
44. Stolen CM, Madanat R, Marti L et al. Semicarbazide sensitive amine oxidase overexpression has dual consequences: Insulin mimicry and diabetes-like complications. FASEB J. 18, 702-704 (2004).
45. Boucher J, Masri B, Daviaud D et al. Apelin, a newly identified adipokine up-regulated by insulin and obesity. Endocrinology 146, 1764-1771 (2005).
46. Yraola F, Garcia-Vicente S, Fernandez-Recio J et al. New efficient substrates for semicarbazide-sensitive amine oxidase/VAP-1 enzyme: Analysis by SARs and computational docking. J. Med. Chem. 49, 6197-6208 (2006).
47. Yraola F, Zorzano A, Albericio F, Royo M. Structure-activity relationships of SSAO/ VAP-1 arylalkylamine-based substrates. ChemMedChem. 4, 495-503 (2009).
48. Bonaiuto E, Lunelli M, Scarpa M, Vettor R, Milan G, DiPaolo ML. A structure-activity study to identify novel and efficient substrates of the human semicarbazide-sensitive amine oxidase/VAP1 enzyme. Biochimie 92, 858-868 (2010).
49. Dray C, Knauf C, Daviaud D et al. Apelin stimulates glucose utilization in normal and obese insulin-resistant mice. Cell Metab. 8, 437-445 (2008).
50. Carpéné C, Dray C, Attané C et al. Expanding role for the apelin/APJ system in physiopathology. J. Physiol. Biochem. 63, 359-374 (2007).
51. Valente T, Solé M, Unzeta M. SSAO/VAP-1 protein expression during mouse embryonic development. Dev. Dyn. 237, 2585-2593 (2008).
52. Wanecq E, Prévot D, Carpéné C. Lack of direct insulin-like action of visfatin/Nampt/ PBEF1 in human adipocytes. J. Physiol. Biochem. 65, 351-360 (2009).
53. Iglesias-Osma MC, Garcia-Barrado MJ, Visentin V et al. Benzylamine exhibits insulin-like effects on glucose disposal, glucose transport, and fat cell lipolysis in rabbits and diabetic mice. J. Pharmacol. Exp. Ther. 309, 1020-1028 (2004).
54. Bour S, Visentin V, Prévot D et al. Effects of oral administration of benzylamine on glucose tolerance and lipid metabolism in rats. J. Physiol. Biochem. 61, 371-379 (2005).
55. Carpéné C. Amine oxidases in adipose tissue-related disorders. In: Copper Amine Oxidases: Structures, Catalytic Mechanisms and Role in Pathophysiology. Floris G, Mondovì B (Eds). CRC Press, FL, USA 177-194 (2009).
56. Hayes GR, Lockwood DH. Role of insulin receptor phosphorylation in the insulinomimetic effects of hydrogen peroxide. Proc. Natl Acad. Sci. USA 84, 8115-8119 (1987).
57. 2 generation in human adipocyte plasma membranes is mediated by Gai2. J. Biol. Chem. 272, 10135-10143 (1997).
58. Mahadev K, Zilbering A, Zhu L, Goldstein BJ. Insulin-stimulated hydrogen peroxide reversibly inhibits protein-tyrosine phosphatase 1B in vivo and enhances the early insulin action cascade. J. Biol. Chem. 276 (24), 21938-61942 (2001).
59. 2 and the sulfonylurea drug, glimepiride, in rat adipocytes depends on cAMP degradation by lipid droplets. Biochemistry 47, 1259-1273 (2008). (Pubitemid 351198703)
60. Andersen A. Final report on the safety assessment of benzaldehyde. Int. J. Toxicol. 25(Suppl. 1), 11-27 (2006).
61. Solé M, Hernandez-Guillamon M, Boada M, Unzeta M. p53 phosphorylation is involved in vascular cell death induced by the catalytic activity of membrane-bound SSAO/VAP-1. Biochim. Biophys. Acta 1783, 1085-1094 (2008).
62. Langford SD, Trent MB, Boor PJ. Cultured rat vascular smooth muscle cells are resistant to methylamine toxicity: No correlation to semicarbazide- sensitive amine oxidase. Cardiovasc. Toxicol. 1, 51-60 (2001).
63. Yu PH, Zuo DM. Formaldehyde produced endogenously via deamination of methylamine. A potential risk factor for initiation of endothelial injury. Atherosclerosis 120, 189-197 (1996).
64. Dunkel P, Gelain A, Barlocco D et al. Semicarbazide-sensitive amine oxidase/ vascular adhesion protein 1: Recent developments concerning substrates and inhibitors of a promising therapeutic target. Curr. Med. Chem. 15, 1827-1839 (2008).
65. O'Sullivan M, MacDougall MB, Unzeta M, Lizcano JM, Tipton KF. Semicarbazidesensitive amine oxidases in pig dental pulp. Biochim. Biophys. Acta. 1647, 333-336 (2003).
66. O'Sullivan J, O'Sullivan M, Tipton KF, Unzeta M, Del Mar Hernandez M, Davey GP. The inhibition of semicarbazide-sensitive amine oxidase by aminohexoses. Biochim. Biophys. Acta. 1647, 367-371 (2003).
67. Kankuri E, Vaali K, Knowles RG et al. Suppression of acute experimental colitis by a highly selective inducible nitric-oxide synthase inhibitor, N-[3-(aminomethyl) benzyl]acetamidine. J. Pharmacol. Exp. Ther. 298, 1128-1132 (2001).
68. Linscheid P, Seboek D, Zulewski H et al. Cytokine-induced metabolic effects in human adipocytes are independent of endogenous nitric oxide. Am. J. Physiol. Endocrinol. Metab. 290, E1068-E1077 (2006).
69. Chalon S, Tarkiainen J, Garreau L et al. Pharmacological characterization of N,N-dimethyl-2-(2-amino-4-methylphenyl thio)benzylamine as a ligand of the serotonin transporter with high affinity and selectivity. J. Pharmacol. Exp. Ther. 304, 81-87 (2003).
70. Jakobsson E, Nilsson J, Ogg D, Kleywegt GJ. Structure of human semicarbazidesensitive amine oxidase/vascular adhesion protein-1. Acta Crystallogr. D Biol. Crystallogr. 61, 1550-1562 (2005).
71. Marti L, Abella A, De La Cruz X et al. Exploring the binding mode of semicarbazide-sensitive amine oxidase/VAP-1: Identification of novel substrates with insulin-like activity. J. Med. Chem. 47, 4865-4874 (2004).
72. Gallardo-Godoy A, Hernandez M, Sanz E, Unzeta M. Synthesis of 4-methyl-thio-phenylpropylamine and the evaluation of its interaction with different amine oxidases. Bioorg. Med. Chem. 12, 273-279 (2004).
73. Wang EY, Gao H, Salter-Cid L et al. Design, synthesis, and biological evaluation of semicarbazide-sensitive amine oxidase (SSAO) inhibitors with anti-inflammatory activity. J. Med. Chem. 49, 2166-2173 (2006).
74. Stolen CM, Marttila-Ichihara F, Koskinen K et al. Absence of the endothelial oxidase AOC3 leads to abnormal leukocyte traffic in vivo. Immunity 22, 105-115 (2005).
75. Lino CS, Sales TP, Gomes PB et al. Anti-diabetic activity of a fraction from Cissus verticillata and tyramine, its main bioactive constituent, in alloxan-induced diabetic rats. Am. J. Pharmacol. Toxicol. 2, 178-188 (2007).
76. Fontana E, Boucher J, Marti L et al. Amine oxidase substrates mimic several of the insulin effects on adipocyte differentiation in 3T3 F442A cells. Biochem. J. 356, 769-777 (2001).
77. Carpéné C, Daviaud D, Boucher J et al. Short- and long-term insulin-like effects of monoamine oxidase and semicarbazidesensitive amine oxidase substrates in cultured adipocytes. Metabolism 55, 1397-1405 (2006).
78. Mercier N, Moldes M, El Hadri K, Fève B. Semicarbazide-sensitive amine oxidase activation promotes adipose conversion of 3T3-L1 cells. Biochem. J. 358, 335-342 (2001).
79. Subra C, Fontana E, Visentin V, Testar X, Carpéné C. Tyramine and benzylamine partially but selectively mimic insulin action on adipose differentiation in 3T3-L1 cells. J. Physiol. Biochem. 59, 209-216 (2003).
80. Bour S, Visentin V, Grès S, Saulnier-Blache JS, Wabitsch M, Carpéné C. Tyramine, benzylamine, and to a lesser extent histamine, partially mimic the adipogenic effect of insulin in a human preadipocyte cell strain. Inflamm. Res. 54(Suppl. 1), S60-S61 (2005).