Selective Inhibitors of Membrane-Bound Semicarbazide-Sensitive Amine Oxidase (SSAO) Activity in Mammalian Tissues

NeuroToxicology

Volumn 25, Issue 1-2, 2004, Pages 325-335

  Kinemuchi, Hiroyasu ^a   Sugimoto, Haruyo ^a   Obata, Toshio ^b   Satoh, Nobunori ^c   Ueda, Shiro ^c  

^a ISHINOMAKI SENSHU UNIVERSITY   (Japan)

^b OITA UNIVERSITY   (Japan)

^c CHIBA UNIVERSITY   (Japan)

Author keywords

2 Bromoethylamine; Diabetic complication; Diabetis; Semicarbazide sensitive amine oxidase (SSAO); SSAO inhibitor; Toxic aldehyde

Indexed keywords

1 METHYL 2 (2 TOLYLOXY)ETHYLAMINE; 1 METHYL 2 (4 TOLYLOXY)ETHYLAMINE; 2 (3,4 DIMETHOXYPHENYL) 3 FLUOROALLYLAMINE; 2 (4 BROMO 2 TOLYLOXY) 1 METHYLETHYLAMINE; 2 (4 BROMO 2,6 XYLYLOXY) 1 METHYLETHYLAMINE; 2 BROMOETHYLAMINE; 3 CHLORO 2 PHENYLALLYLAMINE; 5 AMINOMETHYL 3 [4 (3 CHLOROBENZYLOXY)PHENYL] 2 OXAZOLIDINONE; ALDEHYDE; ALLYLAMINE DERIVATIVE; ALMOXATONE; ALPHA METHYLBENZYLAMINE; AMIFLAMINE; AMINE OXIDASE (COPPER CONTAINING); AMINE OXIDASE (FLAVIN CONTAINING); AMINOGUANIDINE; AMPHETAMINE; BENSERAZIDE; CARBIDOPA; DINORAMIFLAMINE; ENZYME INHIBITOR; FLA 1047; HYDRAZINE DERIVATIVE; ISONIAZID; MEXILETINE; MOFEGILINE; MONOAMINE; NIALAMIDE; NORAMIFLAMINE; PROCARBAZINE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ADIPOSE TISSUE CELL; CELL SURFACE; CYTOTOXICITY; DIABETES MELLITUS; DRUG POTENCY; DRUG SELECTIVITY; ENZYME ACTIVITY; ENZYME BLOOD LEVEL; ENZYME METABOLISM; ENZYME SYNTHESIS; GLUCOSE TRANSPORT; KIDNEY DISEASE; MAMMAL; MEMBRANE BINDING; MUSCLE CELL; NEUROPATHY; NONHUMAN; PLASMA; PRIORITY JOURNAL; RETINOPATHY; REVIEW; STRUCTURE ANALYSIS; VASCULAR SMOOTH MUSCLE;

ANIMALIA; GYMNOMYZA SAMOENSIS; MAMMALIA;

EID: 0348046384     PISSN: 0161813X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0161-813X(03)00118-9     Document Type: Article

References (54)

1. Andree TH, Clark DE. Characteristics and specificity of phenelzine and benzerazide as inhibitors of benzylamine oxidase and monoamine oxidase. Biochem Pharmacol 1982;31:825-30.
2. Arai Y, Toyoshima Y, Kinemuchi H. Studies on monoamine oxidase and semicarbazide sensitive amine oxidase. Part II. Inhibition by α-methylated substrate-analogue monoamines, α-methyltryptamine, α-methylbenzylamine and two enantiomers of α-methylbenzylamine. Jpn J Pharmacol 1986;41:191-7.
3. Barrand MA, Fox SA, Callingham BA. Amine oxidase activities in brown adipose tissue of the rat; identification of semicarbazide-sensitive (clorgyline-resistant) activity at the fat cell membrane. J Pharm Pharmacol 1984;36:652-8.
4. Blaschko HF. The amine oxidases of mammalian blood plasma. Adv Comp Phys Biochem 1962;1:67-116.
5. Bono P, Salmi M, Smith DJ, Jalkanen S. Cloning and characterization of mouse vascular adhesion protein (VAP-1) reveals a novel molecule with enzyme activity. J Immunol 1998;160:5563-71.
6. Boor PJ, Hysmith RM, Sanduja R. A role for a new vascular enzyme in the metabolism of xenobiotic amines. Cir Res 1990;66:249-52.
7. Buffoni, F. Semicarbazide-sensitive amine oxidases: some biochemical properties and general considerations. In: Yu, PM, Tipton, KF, Boulton, AA, editors. Current Neurochemical and Phermacological Aspects of Biogenic Amines. Amsterdam: Raven Press; 1995. p. 323-31.
8. Callingham BA. Substrate selective inhibition of monoamine oxidase by mexiletine. Br J Pharmacol 1977;61:118-9.
9. Callingham, BA, Crosbie, AE, Rous, BA. Some aspects of the pathophysiology of semicarbazide-sensitive amine oxidase enzymes. In: Yu, PM, Tipton, KF, Boulton, AA, editors. Current neurochemical and phermacological aspects of biogenic amines. Amsterdam: Raven Press; 1995. p. 305-21.
10. Ekblom J. Potential therapeutic value of drugs inhibiting semicarbazide-sensitive amine oxidase: vascular cytoprotection in diabetes mellitus. Pharmacol Res 1998;37:87-92.
11. Enrique-Tarancon G, Mart L, Lizcano JM, Unzeta M, Sevilla L, Camp 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 cell. J Biol Chem 1998;273:8025-32.
12. Eriksson M, Fowler CJ. Inhibition of monoamine oxidase and semicarbazide-sensitive amine oxidase by mexiletine and related compounds. Naunyn Schmiedeberg's Arch Pharmacol 1984;327:273-8.
13. Fitzgerald DH, Tipton KF, Lyles GA. Studies on the behaviour of semicarbazide-sensitive amine oxidase in Sprague-Dawley rats treated with the monoamine oxidase inhibitor tranylcypromine. J Neural Transm 1998;52(Suppl):259-64.
14. Fowler CJ. Selective inhibitors of monoamine oxidase types A and B and their clinical usefulness. Drugs Future 1982;2:501-17.
15. Fowler CJ, Mantle TJ, Tipton KF. The nature of the inhibition of rat liver monoamine oxidase types A and B by the acetylenic inhibitors clorgyline, L-deprenyl and pargyline. Biochem Pharmacol 1982;32:3555-61.
16. Fowler CJ, Eriksson M, Thorell G, Magnusson O. Stereoselective inhibition of monoamine oxidase and semicarbazide-sensitive amine oxidase by 4-dimethyl-2-α-dimethylphenethylamine (FLA 336). Naunyn-Schmiedeberg's Arch Pharmacol 1984;327:279-84.
17. Garret NJ, Mantle TJ, Tipton K. Inhibition of monoamine oxidase by amphetamine and related compounds. Biochem Pharmacol 1976;25:2073-7.
18. Holt A, Sharman DF, Callingham BA, Kettler R. Characteristics of procarbazine as an inhibitor in-vitro of rat semicarbazide-sensitive amine oxidase. J Pharm Pharmacol 1992a;44:487-93.
19. Holt A, Sharman DF, Callingham BA. Effects in-vitro of procarbazine metabolites on some amine oxidase activities in the rat. J Pharm Pharmacol 1992b;44:494-9.
20. Holt A, Callingham BA. Location of the active site of rat vascular semicarbazide-sensitive amine oxidase. J Neural Transm 1994;41(Suppl):433-7.
21. Hysmith RM, Boor PJ. Role of benzylamine oxidase in the cytotoxicity of allylamine toward aortic smooth muscle cells. Toxicol 1988;51:133-45.
22. Janes SM, Palcic MM, Scaman CH, Smith AJ, Brown DE, Dooley DM, Mure M, Klinman JP. Identification of topaquinone and its consensus sequence in copper amine oxidases. Biochemistry 1982;31:12147-54.
23. Kinemuchi H, Morikawa F, Tajima H, Kamijo K. Enzymic characteristics of a clorgyline- and L-deprenyl-resistant amine oxidase in human placenta. In Kamijo K, Usdin E, Nagatsu T, editors. Monoamine oxidase: basic and clinical frontiers. Amsterdam: Excerpta Medica; 1982. p. 112-24.
24. Kinemuchi H, Morikawa F, Ueda T. Inhibition of benzylamine oxidase by some selective and reversible MAO inhibitors. In: Tipton KF, Dostert P, Strolin Beneddeti M, editors. Monoamine oxidase and disease, London: Academic Press; 1984. p. 574-5.
25. Kinemuchi H, Morikawa F, Ueda T, Arai Y. Studies of monoamine oxidase and semicarbazide-sensitive amine oxidase. Part I. Inhibition by a selective monoamine oxidase-B inhibitor MD 780236. Jpn J Pharmacol 1986;41:183-9.
26. Kinemuchi H, Jindo M, Tabata A, Tadano T, Toyosima Y, Arai Y, Tadano T, Kisara K, Oreland L. 2-Bromoetyleamine, a suicide inhibitor of tissue-bound semicarbazide-sensitive amine oxidase. Jpn J Pharmacol 2000;83:164-6.
27. Kinemuchi H, Kobayashi N, Takahashi K, Takayanagi K, Arai Y, Tadano T, Oreland L. Inhibition of tissue-bound semicarbazide-sensitive amine oxidase by two haloamines, 2-bromoethylamine and 3-bromopropylamine. Arch Biochem Biophys 2001;385:154-61.
28. Kobayashi N, Takahashi K, Takahashi K, Masuko S, Tadano T, Kisara K, Kinemuchi H. Molecular characteristics of tissue-bound semicarbazide-sensitive amine oxidase (SSAO) in guinea pig tissues. Life Sci 2002;70:1519-31.
29. Lewinsohn R, Bohm K-H, Glover V, Sandler M. A benzylamine oxidase distinct from monoamine oxidase B-widespread distribution in man and rat. Biochem Pharmacol 1978;27:1857-63.
30. Lewinsohn R, Glover V, Sandler M. β-Phenylethylamine and benzylamine as substrates for human monoamine oxidase A: a source of some anomalies. Biochem Pharmacol 1980;29:777-81.
31. Lizcano JM, Balsa D, Tipton KF, Unzeta M. The oxidation of dopamine by the semicarbazide-sensitive amine oxidase (SSAO) from rat vas deferens. Biochem Pharmacol 1991;41:1107-10.
32. Lizcano JM, deArriba AF, Tipton KF, Unzetta M. Inhibition of lung semicarbazide-sensitive amine oxidase (SSAO) by some hydrazine derivatives. Biochem Pharmacol 1996;52:187-95.
33. Lyles GA. The interaction of semicarbazide-sensitive amine oxidase with MAO inhibitors. In: Tipton KF, Dostert P, Strolin Benedett M, editors. Monoamine oxidase and disease, London: Academic Press; 1984. p. 547-56.
34. Lyles GA, Marshall CMS, McDonald IA, Bey P, Ralfreyman MG. Inhibition of rat aorta semicarbazide-sensitive amine oxidase by 2-phenyl-3-haloallylamines and related compounds. Biochem Pharmacol 1987;36:2847-53.
35. Lyles GA. Properties of mammalian tissue-bound semicarbazide-sensitive amine oxidase: possible clues to its physiological function? J Neural Transm 1994;41(Suppl):387-96.
36. Lyles GA. Substrate-specificity of mammalian tissue-bound semicarbazide-sensitive amine oxidase. In: Yu PM, Tipton KF, Boulton AA, editors. Current neurochemical and pharmacological aspects of biogenic amines. Utrecht: Elsevier; 1995. p. 293-303.
37. Lyles GA. Mammalian plasma and tissue-bound semicarbazide-sensitive amine oxidase: biochemical, pharmacological and toxicological aspects. Int J Biochem Cell Biol 1996;28:259-74.
38. 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 Therp 1998;285:342-9.
39. Morikawa F, Ueda T, Arai Y, Kinemuchi H. Inhibition of monoamine oxidase A-form and semicarbazide-sensitive amine oxidase by selective and reversible monoamine oxidase inhibitors amiflamine and FLA 788(+). Pharmacology 1986;32:38-45.
40. Norqvist A, Oreland L. Localization of a semicarbazide-sensitive serotonin-oxidizing enzyme from porcine dental pulp. Biogenic Amines 1989;6:65-74.
41. Obata T, Yamanaka Y. Inhibition of monkey brain semicarbazide-sensitive amine oxidase by various antidepressants. Neurosci Lett 2000;286:131-3.
42. Rando RR, Eigner A. The pseudo irreversible inhibition of monoamine oxidase by allyamine. Mol Pharmacol 1977;13:1005-13.
43. Rando RR. Mechamism-based enzyme inactivators. Pharmacal Rev 1984;36:111-42.
44. Smith DJ, Salmi M, Bono P, Hellman J, Leu T, Jalkannen S. Cloning of vascular adhesion protein-1 reveals a novel multi-functional adhesion molecules. J Exp Med 1998;188:17-27.
45. Strollin-Benedetti M, Dostert P, Boucher T, Guffroy C. A new reversible selective type B monoamine oxidase inhibitor: MD 780236. In: Kamijo K, Usdin E, Nagatsu T, editors. Monoamine oxidase: basic and clinical frontiers. Amsterdam: Excerpta Medica; 1982. p. 209-20.
46. Tabata A, Takahashi K, Masuko S, Aizawa H, Obata T, Oreland L, Kinemuchi H. Further evidence for suiside inhibition of semicarbazide-sensitive amine oxidase (SSAO) in guinea pig lung by 2-bromoethylamine. Methods Find Exp Clin Pharmacol 2002;24(Suppl):83-90.
47. Tipton, KF, Balsa, D, Unzeta, M. Newer approach to the study of monoamine oxidase inhibition. In: Yasuhara H, Parvez SH, Oguchi K, Sandler M, Nagatsu T, editors. Monoamine Oxidase: Basic and Clinical Aspects. VSP: Utrecht; 1993. p. 1-13.
48. Tanizawa K. Biogenesis of novel quinone coenzymes. J Biochem (Tokyo) 1995;118:671-8.
49. Yu PH. Oxidative deamination of aliphatic amines by rat aorta semicarbazide-sensitive amine oxidase. J Pharm Pharmacol 1990;42:882-4.
50. Yu PH, Zuo D-M. Inhibition of a type B monoamine oxidase inhibitor, (E)-2-(4-flu-orophenethyl)-3-fluoroallylamine (MDL-72974A), on semicarbazide-sensitive amine oxidase isolated from vascular tissues and sera of different species. Biochem Pharmacol 1992;43:307-12.
51. Yu PH, Zuo D-M. Oxidative deamination of methylamine by semicarbazide-sensitive amine oxidase leads to cytotoxic damage in endothelial cells. Diabetes 1993;42:594-603.
52. Yu PH, Zuo D-M. Aminoguanizine inhibits semicarbazide-sensitive amine oxidase activity: implication for advanced glycation end product and diabetic complications. Diabetologia 1997;363:1243-50.
53. Yu PH, Davis BA, Deng Y. 2-Bromoetylamine as a potent selective suicide inhibitor for semicarbazide-sensitive amine oxidase. Biochem Pharmacol 2001;61:741-8.
54. Zreika M, McDonald IA, Bey P, Palfreyman MG. MDL 72145, an enzyme-activated irreversible inhibitor with selectivity for monoamine oxidase type B. J Neurochem 1984;43:448-54.