Orientation of oxazolidinones in the active site of monoamine oxidase

Biochemical Pharmacology

Volumn 70, Issue 3, 2005, Pages 407-416

  Jones, Tadeusz Z E ^a   Fleming, Paul ^b   Eyermann, Charles J ^b   Gravestock, Michael B ^b   Ramsay, Rona R ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

Difference spectra; Flexible docking; Kinetics; Monoamine oxidase; Oxazolidinone

Indexed keywords

AMINE; AMINE OXIDASE (FLAVIN CONTAINING); AMINO ACID DERIVATIVE; ANTIINFECTIVE AGENT; IMIDAZOLE DERIVATIVE; LIGAND; MONOAMINE OXIDASE INHIBITOR; NITROGEN; OXAZOLIDINONE DERIVATIVE; QUERCETIN; SEMIQUINONE;

ANTIBACTERIAL ACTIVITY; ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; LIGAND BINDING; PRIORITY JOURNAL; SPECTROSCOPY; STRUCTURE ACTIVITY RELATION;

BINDING SITES; HUMANS; MOLECULAR CONFORMATION; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; OXAZOLIDINONES;

EID: 21344455763     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2005.05.001     Document Type: Article

References (28)

1. H. Kim, S.O. Sablin, and R.R. Ramsay Inhibition of monoamine oxidase A by beta-carboline derivatives Arch Biochem Biophys 337 1997 137 142
2. R.R. Ramsay, and D.J.B. Hunter Inhibitors alter the spectrum and redox properties of monoamine oxidase A BBA Proteins Proteomics 1601 2002 178 184
3. R.M.G. Hynson, J. Wouters, and R.R. Ramsay Monoamine oxidase A inhibitory potency and flavin perturbation are influenced by different aspects of pirlindole inhibitor structure Biochem Pharmacol 65 2003 1867 1874
4. J.C. Ma, M. Yoshimura, E. Yamashita, A. Nakagawa, A. Ito, and T. Tsukihara Structure of rat monoamine oxidase A and its specific recognitions for substrates and inhibitors J Mol Biol 338 2004 103 114
5. S.E.J. Rigby, R.M.G. Hynson, R.R. Ramsay, A.W. Munro, and N.S. Scrutton A stable tyrosyl radical in monoamine oxidase A J Biol Chem 280 2005 4627 4631
6. S.O. Sablin, and R.R. Ramsay Monoamine oxidase contains a redox-active disulfide J Biol Chem 273 1998 14074 14076
7. R.M.G. Hynson, S.M. Kelly, N.C. Price, and R.R. Ramsay Conformational changes in monoamine oxidase A in response to ligand binding or reduction Biochim Biophys Acta Gen Subj 1672 2004 60 66
8. S.O. Sablin, and R.R. Ramsay Substrates but not inhibitors alter the redox potentials of monoamine oxidases Antioxid Redox Signal 3 2001 723 729
9. A.K. Tan, and R.R. Ramsay Substrate-specific enhancement of the oxidative half-reaction of monoamine-oxidase Biochemistry 32 1993 2137 2143
10. F. Mazouz, L. Lebreton, R. Milcent, and C. Burstein 5-Aryl-1,3,4- oxadiazol-2(3h)-one derivatives and sulfur analogs as new selective and competitive monoamine-oxidase type-B inhibitors Eur J Med Chem 25 1990 659 671
11. S. Kneubuhler, U. Thull, C. Altomare, V. Carta, P. Gaillard, and P.A. Carrupt Inhibition of monoamine oxidase-B by 5h-indeno 1,2-C pyridazines - biological-activities, quantitative structure-activity-relationships (Qsars) and 3d-Qsars J Med Chem 38 1995 3874 3883
12. L. Lebreton, O. Curet, S. Gueddari, F. Mazouz, S. Bernard, and C. Burstein Selective and potent monoamine-oxidase type-B inhibitors-2-substituted 5-aryltetrazole derivatives J Med Chem 38 1995 4786 4792
13. C.Z. Ding, and R.B. Silverman 4-(Aminomethyl)-1-aryl-2-pyrrolidinones, a new class of monoamine oxidase-b inactivators J Enzyme Inhib 6 1992 223 231
14. R.R. Ramsay, and M.B. Gravestock Monoamine oxidases: to inhibit or not to inhibit Mini Rev Med Chem 3 2003 129 136
15. O. Curet, G. Damoiseau, N. Aubin, N. Sontag, V. Rovei, and F.X. Jarreau Befloxatone, a new reversible and selective monoamine oxidase-A inhibitor. 1. Biochemical profile J Pharmacol Exp Ther 277 1996 253 264
16. D.K. Hutchinson Oxazolidinone antibacterial agents: a critical review Curr Top Med Chem 3 2003 1021 1042
17. E.J. Antal, P.E. Hendershot, D.H. Batts, W.P. Sheu, N.K. Hopkins, and K.M. Donaldson Linezolid, a novel oxazolidinone antibiotic: assessment of monoamine oxidase inhibition using presser response to oral tyramine J Clin Pharmacol 41 2001 552 562
18. M.V. Cantarini, C.J. Painter, E.M. Gilmore, C. Bolger, C.L. Watkins, and A.M. Hughes Effect of oral linezolid on the pressor response to intravenous tyramine Br J Clin Pharmacol 58 2004 470 475
19. C.Z. Ding, and R.B. Silverman Transformation of heterocyclic reversible monoamine oxidase-b inactivators into irreversible inactivators by N-methylation J Med Chem 36 1993 3606 3610
20. C. Binda, M. Li, F. Hubalek, N. Restelli, D.E. Edmondson, and A. Mattevi Insights into the mode of inhibition of human mitochondrial monoamine oxidase B from high-resolution crystal structures Proc Natl Acad Sci USA 100 2003 9750 9755
21. A.K. Tan, W. Weyler, J.I. Salach, and T.P. Singer Differences in substrate specificities of monoamine oxidase-a from human liver and placenta Biochem Biophys Res Commun 181 1991 1084 1088
22. S.J.H. Brickner, K. Douglas, M.R. Barbachyn, P.R. Manninen, D.A. Ulanowicz, and S.A. Garmon Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant Gram-positive bacterial infections J Med Chem 39 1996 673 679
23. Betts MJ, Zeneca patent WO 9731917, vol. WO 9731917, 1997.
24. P. Bissel, M.C. Bigley, K. Castagnoli, and N. Castagnoli Synthesis and biological evaluation of MAO-A selective 1,4-disubstituted-1,2,3,6- tetrahydropyridinyl substrates Bioorg Med Chem 10 2002 3031 3041
25. C. McMartin, and R.S. Bohacek QXP: powerful, rapid computer algorithms for structure-based drug design J Comput Aided Mol Des 11 1997 333 344
26. C. Binda, P. Newton-Vinson, F. Hubalek, D.E. Edmondson, and A. Mattevi Structure of human monoamine oxidase B, a drug target for the treatment of neurological disorders Nat Struct Biol 9 2002 22 26
27. F. Moureau, J. Wouters, D.P. Vercauteren, S. Collin, G. Evrard, and F. Durant A reversible monoamine-oxidase inhibitor, toloxatone - spectrophotometric and molecular-orbital studies of the interaction with flavin adenine-dinucleotide (FAD) Eur J Med Chem 29 1994 269 277
28. M. Reyes-Parada, A. Fierro, P. Iturriaga-Vasquez, and B.K. Cassles Monoamine oxidase inhibition in the light of new structural data Curr Enzyme Inhib 1 2005 85 95