Multifunctional coumarin derivatives: Monoamine oxidase B (MAO-B) inhibition, anti-β-amyloid (Aβ) aggregation and metal chelation properties against Alzheimer's disease

Bioorganic and Medicinal Chemistry Letters

Volumn 25, Issue 3, 2015, Pages 508-513

  Huang, Ming ^a   Xie, Sai Sai ^a   Jiang, Neng ^a   Lan, Jin Shuai ^a   Kong, Ling Yi ^a   Wang, Xiao Bing ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Alzheimer's disease; Coumarin derivatives; MAO; Metal chelator; Amyloid aggregation

Indexed keywords

AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; AMYLOID BETA PROTEIN[1-42]; CHELATING AGENT; COUMARIN DERIVATIVE; CURCUMIN; IPRONIAZID; MONOAMINE OXIDASE INHIBITOR; PARGYLINE; RESVERATROL; AMINE OXIDASE (FLAVIN CONTAINING); AMYLOID BETA PROTEIN; METAL;

ALZHEIMER DISEASE; ANIMAL CELL; ARTICLE; BLOOD BRAIN BARRIER; CELL VIABILITY; CHELATION; DRUG DESIGN; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; HYDROGEN BOND; IC50; IN VITRO STUDY; NONHUMAN; PC12 CELL LINE; PHEOCHROMOCYTOMA; PROTEIN AGGREGATION; RAT; STRUCTURE ACTIVITY RELATION; ANIMAL; BINDING SITE; CELL SURVIVAL; CHEMISTRY; DRUG EFFECTS; METABOLISM; MOLECULAR DOCKING; PATHOLOGY; PROTEIN TERTIARY STRUCTURE; TUMOR CELL LINE;

RATTUS;

ALZHEIMER DISEASE; AMYLOID BETA-PEPTIDES; ANIMALS; BINDING SITES; BLOOD-BRAIN BARRIER; CELL LINE, TUMOR; CELL SURVIVAL; CHELATING AGENTS; COUMARINS; DRUG DESIGN; HUMANS; METALS; MOLECULAR DOCKING SIMULATION; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; PC12 CELLS; PROTEIN STRUCTURE, TERTIARY; RATS;

EID: 84920863051     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2014.12.034     Document Type: Article

References (60)

1. H.W. Querfurth, and F.M. LaFerla N. Engl. J. Med. 362 2010 329
2. E. Scarpini, P. Schelterns, and H. Feldman Lancet Neurol. 2 2003 539
3. M. Rosini, E. Simoni, A. Milelli, A. Minarini, and C. Melchiorre J. Med. Chem. 57 2014 2821
4. R. Von Bernhardi, and J. Eugenin Antioxid. Redox Signal. 16 2012 974
5. M.B. Youdim, D. Edmondson, and K.F. Tipton Nat. Rev. Neurosci. 7 2006 295
6. P. Riederer, W. Danielczyk, and E. Grünblatt Neurotoxicology 25 2004 271
7. J. Saura, J.M. Luque, A.M. Cesura, M.D. Prada, V. Chan-Palay, G. Huber, J. Löffler, and J.G. Richards Neuroscience 62 1994 15
8. M. Nebbioso, A. Pascarella, C. Cavallotti, and N. Pescosolido Int. J. Exp. Pathol. 93 2012 401
9. M. Sano, C. Ernesto, R.G. Thomas, M.R. Klauber, K. Schafer, M. Grundman, P. Woodbury, J. Growdon, C.W. Cotman, and E. Pfeiffer N. Engl. J. Med. 336 1997 1216
10. M. Naoi, and W. Maruyama Curr. Pharm. Des. 16 2010 2799
11. J. Hardy, and D.J. Selkoe Science 297 2002 353
12. A.S. DeToma, J. Krishnamoorthy, Y. Nam, H.J. Lee, J.R. Brender, A. Kochi, D. Lee, V. Onnis, C. Congiu, and S. Manfredini Chem. Sci. 5 2014 4851
13. A.S. DeToma, S. Salamekh, A. Ramamoorthy, and M.H. Lim Chem. Soc. Rev. 41 2012 608
14. R. Yesuvadian, J. Krishnamoorthy, A. Ramamoorthy, and A. Bhunia Biochem. Biophys. Res. Commun. 447 2014 590
15. H.R. Patel, A.S. Pithadia, J.R. Brender, C.A. Fierke, and A. Ramamoorthy J. Phys. Chem. Lett. 5 2014 1864
16. S.A. Kotler, P. Walsh, J.R. Brender, and A. Ramamoorthy Chem. Soc. Rev. 43 2014 6692
17. M.G. Savelieff, Y. Liu, R.R. Senthamarai, K.J. Korshavn, H.J. Lee, A. Ramamoorthy, and M.H. Lim Chem. Commun. 2014 5301
18. Y. Suzuki, J.R. Brender, M.T. Soper, J. Krishnamoorthy, Y. Zhou, B.T. Ruotolo, N.A. Kotov, A. Ramamoorthy, and E.N. Marsh Biochemistry 52 2013 1903
19. W. Luo, Y.P. Li, Y. He, S.L. Huang, D. Li, L.Q. Gu, and Z.S. Huang Eur. J. Med. Chem. 46 2011 2609
20. D. Liu, Y. Xu, Y. Feng, H. Liu, X. Shen, K. Chen, J. Ma, and H. Jiang Biochemistry 45 2006 10963
21. C. Opazo, X. Huang, R.A. Cherny, R.D. Moir, A.E. Roher, A.R. White, R. Cappai, C.L. Masters, R.E. Tanzi, and N.C. Inestrosa J. Biol. Chem. 277 2002 40302
22. P. Zatta, D. Drago, S. Bolognin, and S.L. Sensi Trends Pharmacol. Sci. 30 2009 346
23. X. Huang, R.D. Moir, R.E. Tanzi, A.I. Bush, and J.T. Rogers Ann. N. Y. Acad. Sci. 1012 2004 153
24. A.I. Bush J. Alzheimers Dis. 15 2008 223
25. S.J. Hyung, A.S. DeToma, J.R. Brender, S. Lee, S. Vivekanandan, A. Kochi, J.S. Choi, A. Ramamoorthy, B.T. Ruotolo, and M.H. Lim Proc. Natl. Acad. Sci. USA 110 2013 3743
26. M.R. Jones, E.L. Service, J.R. Thompson, M.C. Wang, I.J. Kimsey, A.S. DeToma, A. Ramamoorthy, M.H. Lim, and T. Storr Metallomics 4 2012 910
27. J.J. Braymer, J.S. Choi, A.S. DeToma, C. Wang, K. Nam, J.W. Kampf, A. Ramamoorthy, and M.H. Lim Inorg. Chem. 50 2011 10724
28. J.S. Choi, J.J. Braymer, R.P. Nanga, A. Ramamoorthy, and M.H. Lim Proc. Natl. Acad. Sci. USA 107 2010 21990
29. H. Zheng, M.B. Youdim, and M. Fridkin ACS Chem. Neurosci. 1 2010 737
30. S. Lee, X. Zheng, J. Krishnamoorthy, M.G. Savelieff, H.M. Park, J.R. Brender, J.H. Kim, J.S. Derrick, A. Kochi, H.J. Lee, C. Kim, A. Ramamoorthy, M.T. Bowers, and M.H. Lim J. Am. Chem. Soc. 136 2014 299
31. Z.C. Xu, X.B. Wang, W.Y. Yu, S.S. Xie, S.Y. Li, and L.Y. Kong Bioorg. Med. Chem. Lett. 24 2014 2368
32. L. Huang, C. Lu, Y. Sun, F. Mao, Z. Luo, T. Su, H. Jiang, W. Shan, and X. Li J. Med. Chem. 55 2012 8483
33. Y. Yang, Q.W. Liu, Y. Shi, Z.G. Song, Y.H. Jin, and Z.Q. Liu Eur. J. Med. Chem. 84 2014 1
34. S.S. Xie, X.B. Wang, J.Y. Li, L. Yang, and L.Y. Kong Eur. J. Med. Chem. 64 2013 540
35. L. Piazzi, A. Cavalli, F. Colizzi, F. Belluti, M. Bartolini, F. Mancini, M. Recanatini, V. Andrisano, and A. Rampa Bioorg. Med. Chem. Lett. 18 2008 423
36. O.M. Abdelhafez, K.M. Amin, H.I. Ali, M.M. Abdalla, and R.Z. Batran Neurochem. Int. 62 2013 198
37. C. Gnerre, M. Catto, F. Leonetti, P. Weber, P.A. Carrupt, C. Altomare, A. Carotti, and B. Testa J. Med. Chem. 43 2000 4747
38. M.J. Matos, C. Teran, C.Y. Perez, E. Uriarte, L. Santana, and D. Vina J. Med. Chem. 54 2011 7127
39. Z.X. Pan, X. He, Y.Y. Chen, W.J. Tang, J.B. Shi, Y.L. Tang, B.A. Song, J. Li, and X.H. Liu Eur. J. Med. Chem. 80 2014 278
40. P.O. Patil, S.B. Bari, S.D. Firke, P.K. Deshmukh, S.T. Donda, and D.A. Patil Bioorg. Med. Chem. 21 2013 2434
41. D.D. Soto-Ortega, B.P. Murphy, F.J. Gonzalez-Velasquez, K.A. Wilson, F. Xie, Q. Wang, and M.A. Moss Bioorg. Med. Chem. 19 2011 2596
42. J.T. Rogers, and D.K. Lahiri Curr. Drug Targets 5 2004 535
43. C.W. Ritchie, A.I. Bush, A. Mackinnon, S. Macfarlane, M. Mastwyk, L. MacGregor, L. Kiers, R. Cherny, Q.-X. Li, and A. Tammer Arch. Neurol. 60 2003 1685
44. M. Pudlo, V. Luzet, L. Ismaïli, I. Tomassoli, A. Iutzeler, and B. Refouvelet Bioorg. Med. Chem. 22 2014 2496
45. B.S. Creaven, B. Duff, D.A. Egan, K. Kavanagh, G. Rosair, V.R. Thangella, and M. Walsh Inorg. Chim. Acta 363 2010 4048
46. B.S. Creaven, E. Czegledi, M. Devereux, E.A. Enyedy, A. Foltyn-Arfa Kia, D. Karcz, A. Kellett, S. McClean, N.V. Nagy, A. Noble, A. Rockenbauer, T. Szabo-Planka, and M. Walsh Dalton Trans. 39 2010 10854
47. B.S. Creaven, M. Devereux, D. Karcz, A. Kellett, M. McCann, A. Noble, and M. Walsh J. Inorg. Biochem. 103 2009 1196
48. A. Kathuria, N. Priya, K. Chand, P. Singh, A. Gupta, S. Jalal, S. Gupta, H.G. Raj, and S.K. Sharma Bioorg. Med. Chem. 20 2012 1624
49. L. Santana, H. González-Díaz, E. Quezada, E. Uriarte, M. Yáñez, D. Vina, and F. Orallo J. Med. Chem. 51 2008 6740
50. A. Carotti, C. Altomare, M. Catto, C. Gnerre, L. Summo, A. De Marco, S. Rose, P. Jenner, and B. Testa Chem. Biodivers. 3 2006 134
51. L.J. Legoabe, A. Petzer, and J.P. Petzer Eur. J. Med. Chem. 49 2012 343
52. M. Bartolini, C. Bertucci, M.L. Bolognesi, A. Cavalli, C. Melchiorre, and V. Andrisano ChemBioChem 8 2007 2152
53. W. Huang, D. Lv, H. Yu, R. Sheng, S.C. Kim, P. Wu, K. Luo, J. Li, and Y. Hu Bioorg. Med. Chem. 18 2010 5610
54. R. Joseph, B. Ramanujam, A. Acharya, A. Khutia, and C.P. Rao J. Org. Chem. 73 2008 5745
55. W.M. Pardridge Alzheimers Dement. 5 2009 427
56. V. Hachinski, and T.-Y. Lee Alzheimers Dement. 5 2009 435
57. L. Di, E.H. Kerns, K. Fan, O.J. McConnell, and G.T. Carter Eur. J. Med. Chem. 38 2003 223
58. P.P. Bose, U. Chatterjee, I. Hubatsch, P. Artursson, T. Govender, H.G. Kruger, M. Bergh, J. Johansson, and P.I. Arvidsson Bioorg. Med. Chem. 18 2010 5896
59. Y.P. Chen, Z.Y. Zhang, Y.P. Li, D. Li, S.L. Huang, L.Q. Gu, J. Xu, and Z.S. Huang Eur. J. Med. Chem. 66 2013 22
60. A.J. Veloso, D. Dhar, A.M. Chow, B. Zhang, D.W. Tang, H.V. Ganesh, S. Mikhaylichenko, I.R. Brown, and K. Kerman ACS Chem. Neurosci. 4 2013 339