Hydrazine and amphetamine binding to amine oxidases: Old drugs with new prospects

Journal of Neural Transmission

Volumn 114, Issue 6, 2007, Pages 743-746

  Knowles, P ^a   Kurtis, C ^a   Murray, J ^a   Saysell, C ^a   Tambyrajah, W ^a   Wilmot, C ^a   McPherson, M ^a   Phillips, S ^a   Dooley, D ^b   Brown, D ^b   Rogers, M ^b   Mure, M ^c  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b MONTANA STATE UNIVERSITY   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

2 hydrazinopyridine (2 HP); 2 phenylcyclopropylamine (TCP); Amine oxidase; pH; Trihydroxyphenylalanine (TPQ)

Indexed keywords

2 HYDRAZINOPYRIDINE; AMINE OXIDASE (COPPER CONTAINING); AMPHETAMINE; HYDRAZINE; HYDRAZONE DERIVATIVE; PHENETHYLAMINE; PYRIDINE DERIVATIVE; TRANYLCYPROMINE; UNCLASSIFIED DRUG;

CATALYSIS; CHROMATOPHORE; CONFERENCE PAPER; DRUG BINDING; DRUG STRUCTURE; ENANTIOMER; ENZYME INHIBITION; KINETICS; PRIORITY JOURNAL; STEREOSPECIFICITY;

AMINE OXIDASE (COPPER-CONTAINING); AMPHETAMINES; BINDING SITES; CATALYTIC DOMAIN; COPPER; ENZYME INHIBITORS; HYDRAZINES; ISOMERISM; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; MONOAMINE OXIDASE INHIBITORS; PROTEIN BINDING; PYRIDONES; TRANYLCYPROMINE;

EID: 34250795269     PISSN: 03009564     EISSN: 14351463     Source Type: Journal    
DOI: 10.1007/s00702-007-0681-0     Document Type: Conference Paper

References (28)

1. AA Coleman O Hindsgaul MM Palcic 1989 Stereochemistry of copper amine oxidase reactions J Biol Chem 264 19500 19505
2. D Collison PF Knowles FE Mabbs FX Rius I Singh DM Dooley CE Cote M McGuirl 1989 Studies on the active site of pig plasma amine oxidase Biochem J 264 663 669
3. D De Biase E Agostinelli G de Matteis B Mondovi L Morpurgo 1996 Half-of-the-sites reactivity of bovine serum amine oxidase. Reactivity and chemical identity of the second site Eur J Biochem 237 93 99
4. F Fulop L Lazar Z Szakonyi M Pihlavisto S Alasanta PJ Vainio A Juhakoski A Marjamaki DA Smith 2004 Discovery of new anti-inflammatory agents Pure Appl Chem 76 965 972
5. S Jalkanen M Salmi 2001 Cell surface monoamine oxidases: enzymes in search of a function EMBO J 20 3893 3901
6. SM Janes JP Klinman 1991 An investigation of bovine serum amine oxidase active site stoichiometry: evidence for an aminotransferase mechanism involving two carbonyl cofactors per enzyme dimer Biochemistry 30 4599 4605
7. SM Janes D Mu D Wemmer AJ Smith S Kaur D Matby AL Burlingame JP Klinman 1990 New redox cofactor in eukaryotic enzymes: 6-hydroxydopa at the active site of bovine serum amine oxidase Science 248 981 987
8. SH Kennedy 1997 Continuation and maintenance treatments in major depression: the neglected role of monoamine oxidase inhibitors J Psychiatry Neurosci 22 127 131
9. K Kenyon S Contente PC Trackman J Tang HM Kagan RF Friedman 1991 Lysyl oxidase and rrg messenger RNA Science 253 802 802
10. PF Knowles DM Dooley 1994 Amine oxidases H Sigel A Sigel Metal ions in biological systems 30 Marcel Dekker New York
11. A Lindstrom B Olsson G Pettersson 1974 Transient kinetics of benzaldehyde formation during the catalytic action of pig-plasma benzylamine oxidase Eur J Biochem 42 177 182
12. AG Mallinger JM Himmelhoch ME Thase DJ Edwards S Knopf 1990 Plasma tranylcypromine: relationship to pharmacokinetic variables and clinical antidepressant actions J Clin Psychopharmacol 10 176 183
13. HW Moises H Beckmann 1981 Antidepressant efficacy of tranylcypromine isomers: a controlled study J Neural Transm 50 185 192
14. L Morpurgo O Befani S Sabatini B Mondovi M Artico F Corelli S Massa G Stefancich L Avigliano 1988 Spectroscopic studies of the reaction between bovine serum amine oxidase (copper-containing) and some hydrazides and hydrazines Biochem J 256 565 570
15. L Morpurgo E Agostinelli B Mondovi L Avigliano R Silvestre G Stefancich M Artice 1992 Bovine serum amine oxidase: half-site reactivity with phenylhydrazine, semicarbazide, and aromatic hydrazides Biochemistry 31 2615 2621
16. M Mure SA Mills JP Klinman 2002 Catalytic mechanism of the topa quinone containing copper amine oxidases Biochemistry 41 9269 9278
17. M Mure DE Brown C Saysell MS Rogers CM Wilmot CR Kurtis MJ McPherson SE Phillips PF Knowles DM Dooley 2005a Role of the interactions between the active site base and the substrate Schiff base in amine oxidase catalysis. Evidence from structural and spectroscopic studies of the 2-hydrazinopyridine adduct of Escherichia coli amine oxidase Biochemistry 44 1568 1582
18. M Mure CR Kurtis DE Brown MS Rogers WS Tambyrajah C Saysell CM Wilmot SEV Phillips PF Knowles DM Dooley MJ McPherson 2005b Active site rearrangement of the 2-hydrazinopyridine adduct in Escherichia coli amine oxidase to an azo copper(II) chelate form: a key role for tyrosine 369 in controlling the mobility of the TPQ-2HP adduct Biochemistry 44 1583 1594
19. MR Parsons MA Convery CM Wilmot KDS Yadav V Blakeley AS Corner SEV Phillips MJ McPherson PF Knowles 1995 Crystal structure of a quinoenzyme: copper amine oxidase of Escherichia coli at 2 A resolution Structure 3 1171 1184
20. max shifts and their dependence on pH for the 2-hydrazinopyridine derivative of two amine oxidases J Mol Catal B Enzym 8 17 25
21. CG Saysell WS Tambyrajah JM Murray CM Wilmot SEV Phillips MJ McPherson PF Knowles 2002 Probing the catalytic mechanism of Escherichia coli amine oxidase using mutational variants and a reversible inhibitor as a substrate analogue Biochem J 365 1 8
22. CH Scaman MM Palcic 1992 Stereochemical course of tyramine oxidation by semicarbazide-sensitive amine oxidase Biochemistry 31 6829 6841
23. HG Schwelberger 2006 Origins of plasma amine oxidases in different mammalian species Inflamm Res 55 Suppl 1 S57 S58
24. KF Tipton 1990 The design and behaviour of selective monoamine oxidase inhibitors B Leonard P Spencer Antidepressants: Thirty Years On" CNS Publ. London 193 203
25. EY Wang G Hongfeng L Salter-Cid L Huang EM Podar A Miller J Zhao A O'Rourke MD Linnik 2006 Design, synthesis, and biological evaluation of semicarbazide-sensitive amine oxidase (SSAO) inhibitors with anti-inflammatory activity J Med Chem 49 2166 2173
26. H Weber-Grandke G Hahn E Mutschler W Mohrke P Langguth H Spahn-Langguth 1993 The pharmacokinetics of tranylcypromine enantiomers in healthy subjects after oral administration of racemic drug and the single enantiomers Br J Clin Pharmacol 36 363 365
27. CM Wilmot JM Murray G Alton MR Parsons MA Convery V Blakeley AS Corner MM Palcic PF Knowles MJ McPherson SEV Phillips 1997 Catalytic mechanism of the quinoenzyme amine oxidase from Escherichia coli: exploring the reductive half-reaction Biochemistry 36 1608 1620
28. CM Wilmot CG Saysell A Blessington DA Conn CR Kurtis MJ McPherson PF Knowles SEV Phillips 2004 Medical implications from the crystal structure of a copper-containing amine oxidase complexed with the antidepressant drug tranylcypromine FEBS Lett 576 301 305