8-Aryl- and alkyloxycaffeine analogues as inhibitors of monoamine oxidase

European Journal of Medicinal Chemistry

Volumn 46, Issue 8, 2011, Pages 3474-3485

  Strydom, Belinda ^a   Bergh, Jacobus J ^a   Petzer, Jacobus P ^a  

^a NORTH WEST UNIVERSITY   (South Africa)

Author keywords

8 Alkyloxycaffeine; 8 Aryloxycaffeine; Caffeine; Molecular docking; Monoamine oxidase; Reversible inhibition

Indexed keywords

8 (2 PHENOXYETHOXY)CAFFEINE; 8 (3 METHYLBUTOXY)CAFFEINE; 8 (3 PHENYLPROPOXY)CAFFEINE; 8 (4 BROMOBENZYLOXY)CAFFEINE; 8 (4 CHLOROBENZYLOXY)CAFFEINE; 8 (CYCLOHEX 3 EN 1 YLMETHOXY)CAFFEINE; 8 [(5 METHYLHEXYL)OXY]CAFFEINE; 8 [2 (4 BROMOPHENOXY)ETHOXY]CAFFEINE; 8 [2 (4 CHLOROPHENOXY)ETHOXY]CAFFEINE; 8 [2 (BENZYLOXY)ETHOXY]CAFFEINE; 8 BENZYLOXYCAFFEINE; 8 CYCLOHEXYLMETHOXYCAFFEINE; 8 CYCLOPENTYLMETHOXYCAFFEINE; 8 PHENOXYCAFFEINE; CAFFEINE DERIVATIVE; MONOAMINE OXIDASE A INHIBITOR; MONOAMINE OXIDASE B INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG PROTEIN BINDING; ENZYME INHIBITION; IC 50;

ALKYLATION; ANIMALS; BINDING SITES; CAFFEINE; HALOGENS; HUMANS; INHIBITORY CONCENTRATION 50; KINETICS; KYNURAMINE; MICE; MODELS, MOLECULAR; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; NEURODEGENERATIVE DISEASES; PROTEIN BINDING; PSYCHOTIC DISORDERS; PSYCHOTROPIC DRUGS; RECOMBINANT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 80955177129     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.05.014     Document Type: Article

References (45)

1. M.B.H. Youdim, and Y.S. Bakhle Monoamine oxidase: isoforms and inhibitors in Parkinson's disease and depressive illness Br. J. Pharmacol. 147 2006 S287 S296
2. 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 (Pubitemid 34049174)
3. M.B.H. Youdim, D.E. Edmondson, and K.F. Tipton The therapeutic potential of monoamine oxidase inhibitors Nat. Rev. Neurosci. 7 2006 295 309
4. M.B.H. Youdim, and M. Weinstock Therapeutic applications of selective and non-selective inhibitors of monoamine oxidase A and B that do not cause significant tyramine potentiation Neurotoxicology 25 2004 243 250 (Pubitemid 38044185)
5. U. Bonnet Moclobemide: therapeutic use and clinical studies CNS. Drug Rev. 9 2003 97 140 (Pubitemid 36438138)
6. H.H. Fernandez, and J.J. Chen Monoamine oxidase-B inhibition in the treatment of Parkinson's disease Pharmacotherapy 27 2007 174S 185S (Pubitemid 350234307)
7. G.G.S. Collins, M. Sandler, E.D. Williams, and M.B.H. Youdim Multiple forms of human brain monoamine oxidase Nature 225 1970 817 820
8. P. Riederer, and M.B.H. Youdim Monoamine oxidase activity and monoamine metabolism in brains of parkinsonian patients treated with l-deprenyl J. Neurochem. 46 1986 1359 1365 (Pubitemid 16062531)
9. D.A. Di Monte, L.E. DeLanney, I. Irwin, J.E. Royland, P. Chan, M.W. Jacowec, and J.W. Langston Monoamine oxidase-dependent metabolism of dopamine in the striatum and substantia nigra of L-DOPA-treated monkeys Brain Res. 738 1996 53 59 (Pubitemid 26379645)
10. J.P. Finberg, J. Wang, K. Bankiewich, J. Harvey-White, I.J. Kopin, and D.S. Goldstein Increased striatal dopamine production from L-DOPA following selective inhibition of monoamine oxidase B by R(+)-N-propargyl-1-aminoindan (rasagiline) in the monkey J. Neural Transm. Suppl. 52 1998 279 285
11. W. Birkmayer, P. Riederer, M.B.H. Youdim, and W. Linaur The potentiation of the anti-akinetic effect after L-dopa treatment by an inhibitor of MAO-B, L-deprenyl J. Neural Transm. 36 1975 303 326
12. M. Gesi, A. Santinami, R. Ruffoli, G. Conti, and F. Fornai Novel aspects of dopamine oxidative metabolism. Confounding outcomes take place of certainties Pharmacol. Toxicol. 89 2001 217 224 (Pubitemid 33070921)
13. F. Fornai, G. Battaglia, M. Gesi, F.S. Giorgi, F. Orzi, and F. Nicoletti Time-course and dose-response study on the effects of chronic L-DOPA administration on striatal dopamine levels and dopamine transporter following MPTP toxicity Brain Res. 887 2000 110 117 (Pubitemid 32008029)
14. S.A. Marchitti, R.A. Deitrich, and V. Vasiliou Neurotoxicity and metabolism of the catecholamine-derived 3,4-dihydroxyphenylacetaldehyde and 3,4-dihydroxyphenylglycolaldehyde: the role of aldehyde dehydrogenase Pharmacol. Rev. 59 2007 125 150 (Pubitemid 46855437)
15. 2A receptors for Parkinson's disease Neurotherapeutics 6 2009 141 151
16. A. Nicotra, F. Pierucci, H. Parvez, and O. Santori Monoamine oxidase expression during development and aging Neurotoxicology 25 2004 155 165 (Pubitemid 38044177)
17. J.S. Fowler, N.D. Volkow, G.J. Wang, J. Logan, N. Pappas, C. Shea, and R. MacGregor Age-related increases in brain monoamine oxidase B in living healthy human subjects Neurobiol. Aging 18 1997 431 435 (Pubitemid 27435085)
18. R.N. Kalaria, M.J. Mitchell, and S.I. Harik Monoamine oxidases of the human brain and liver Brain 111 1988 1441 1451 (Pubitemid 19028462)
19. J.M. Rabey, I. Sagi, M. Huberman, E. Melamed, A. Korczyn, N. Giladi, R. Inzelberg, R. Djaldetti, C. Klein, and G. Berecz Rasagiline mesylate, a new MAO-B inhibitor for the treatment of Parkinson's disease: a double-blind study as adjunctive therapy to levodopa Clin. Neuropharmacol. 23 2000 324 330 (Pubitemid 32047014)
20. C.J. Fowler, A. Wiberg, L. Oreland, and B. Winblad Titration of human brain type-B monoamine oxidase Neurochem. Res. 5 1980 697 708 (Pubitemid 11250886)
21. L.H.A. Prins, J.P. Petzer, and S.F. Malan Inhibition of monoamine oxidase by indole and benzofuran derivatives Eur. J. Med. Chem. 45 2010 4458 4466
22. K.F. Tipton, S. Boyce, J. O'Sullivan, G.P. Davey, and J. Healy Monoamine oxidases: certainties and uncertainties Curr. Med. Chem. 11 2004 1965 1982 (Pubitemid 38967723)
23. J.S. Fowler, N.D. Volkow, J. Logan, G. Wang, R.R. MacGregor, D. Schlyer, A.P. Wolf, N. Pappas, D. Alexoff, C. Shea, E. Dorflinger, L. Kruchowy, K. Yoo, E. Fazzini, and C. Patlak Slow recovery of human brain MAO B after L-deprenyl (selegeline) withdrawal Synaps 18 1994 86 93 (Pubitemid 24308128)
24. 2A receptor antagonists Bioorg. Med. Chem. 11 2003 1299 1310 (Pubitemid 36293525)
25. E.M. Van der Walt, E.M. Milczek, S.F. Malan, D.E. Edmondson, N. Castagnoli, J.J. Bergh, and J.P. Petzer Inhibition of monoamine oxidase by (E)-styrylisatin analogues Bioorg. Med. Chem. Lett. 19 2009 2509 2513
26. 2A receptor by (E, E)-8-(4-phenylbutadien-1-yl)caffeine analogues Bioorg. Med. Chem. 16 2008 8676 8684
27. B. Strydom, S.F. Malan, N. Castagnoli, J.J. Bergh, and J.P. Petzer Inhibition of monoamine oxidase by 8-benzyloxycaffeine analogues Bioorg. Med. Chem. 18 2010 1018 1028
28. C. Binda, J. Wang, L. Pisani, C. Caccia, A. Carotti, P. Salvati, D.E. Edmondson, and A. Mattevi Structures of human monoamine oxidase B complexes with selective noncovalent inhibitors: safinamide and coumarin analogs J. Med. Chem. 50 2007 5848 5852 (Pubitemid 350106038)
29. R.C. Huston, W.F. Allen, Caffeine derivatives. I. The 8-ethers of caffeine, J. Am. Chem. Soc. 56 (1934) 1356-1358.
30. W. Baumann Die nervenkrankenfürsorge der stadt essen Z. Gesamte Neurol. Psychiatr. 15 1913 114 121
31. E. Fischer, and L. Reese Ueber caffeïn, xanthin und guanin Justus Liebigs Ann. Chem. 221 1883 336 344
32. L. Novaroli, M. Reist, E. Favre, A. Carotti, M. Catto, and P.A. Carrupt Human recombinant monoamine oxidase B as reliable and efficient enzyme source for inhibitor screening Bioorg. Med. Chem. 13 2005 6212 6217 (Pubitemid 41400144)
33. 50) of an enzymatic reaction Biochem. Pharmacol. 22 1973 3099 3108
34. F. Hubálek, C. Binda, A. Khalil, M. Li, A. Mattevi, N. Castagnoli, and D.E. Edmondson Demonstration of isoleucine 199 as a structural determinant for the selective inhibition of human monoamine oxidase B by specific reversible inhibitors J. Biol. Chem. 280 2005 15761 15766 (Pubitemid 40616695)
35. D. Van den Berg, K.R. Zoellner, M.O. Ogunrombi, S.F. Malan, G. Terre'Blanche, N. Castagnoli, J.J. Bergh, and J.P. Petzer Inhibition of monoamine oxidase B by selected benzimidazole and caffeine analogues Bioorg. Med. Chem. 15 2007 3692 3702 (Pubitemid 46635144)
36. 2A receptor antagonist (E)-8-(3-chlorostyryl)caffeine (CSC) Bioorg. Med. Chem. 14 2006 3512 3521
37. S.-Y. Son, J. Ma, Y. Kondou, M. Yoshimura, E. Yamashita, and T. Tsukihara Structure of human monoamine oxidase A at 2.2-A resolution: the control of opening the entry for substrates/inhibitors Proc. Natl. Acad. Sci. U.S.A 105 2008 5739 5744 (Pubitemid 351758442)
38. Accelrys Discovery Studio 1.7 2006 Accelrys Software Inc. San Diego, CA, USA http://www.accelrys.com
39. C.I. Manley-King, J.J. Bergh, and J.P. Petzer Inhibition of monoamine oxidase by selected C5- and C6-substituted isatin analogues Bioorg. Med. Chem. 19 2011 261 274
40. C. Binda, R. Angelini, R. Federico, P. Ascenzi, and A. Mattevi Structural bases for inhibitor binding and catalysis in polyamine oxidase Biochemistry 40 2001 2766 2776 (Pubitemid 32198278)
41. E. Fischer Ueber caffeïn, Theobromin, xanthin und guanin Justus Liebigs Ann. Chem. 215 1882 253 320
42. M. Sono, N. Toyoda, K. Shimizu, E. Noda, Y. Shizuri, and M. Tori Functionalization including fluorination of nitrogen-containing compounds using electrochemical oxidation Chem. Pharm. Bull. 44 1996 1141 1145 (Pubitemid 26247165)
43. M.O. Ogunrombi, S.F. Malan, G. Terre'Blanche, N. Castagnoli, J.J. Bergh, and J.P. Petzer Structure-activity relationships in the inhibition of monoamine oxidase B by 1-methyl-3-phenylpyrroles Bioorg. Med. Chem. 16 2008 2463 2472 (Pubitemid 351380937)
44. C.I. Manley-King, G. Terre'Blanche, N. Castagnoli, J.J. Bergh, and J.P. Petzer Inhibition of monoamine oxidase B by N-methyl-2-phenylmaleimides Bioorg. Med. Chem. 17 2009 3104 3110
45. W.L. DeLano, The PyMOL Molecular Graphics System. DeLano Scientific, San Carlos, USA, 2002.