Chalcones: A valid scaffold for monoamine oxidases inhibitors

Journal of Medicinal Chemistry

Volumn 52, Issue 9, 2009, Pages 2818-2824

  Chimenti, Franco ^a   Fioravanti, Rossella ^a   Bolasco, Adriana ^a   Chimenti, Paola ^a   Secci, Daniela ^a   Rossi, Francesca ^a   Yáñez, Matilde ^b   Orallo, Francisco ^b   Ortuso, Francesco ^c   Alcaro, Stefano ^c  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^c UNIVERSITY MAGNA GRAECIA OF CATANZARO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; CHALCONE DERIVATIVE; CHLORINE; HYDROXYL GROUP; MONOAMINE OXIDASE INHIBITOR;

ARTICLE; CRYSTAL STRUCTURE; DRUG MECHANISM; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; MOLECULAR DOCKING; MOLECULAR MODEL; X RAY CRYSTALLOGRAPHY;

CHALCONES; CRYSTALLOGRAPHY, X-RAY; DATABASES, PROTEIN; DRUG DESIGN; HUMANS; INHIBITORY CONCENTRATION 50; ISOENZYMES; MODELS, MOLECULAR; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS;

EID: 65649087484     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm801590u     Document Type: Article

References (49)

1. Kalgutkar, A. S.; Castagnoli, N., Jr. Selective inhibitors of monoamino oxidase (MAO-A and MAO-B) as probes of its catalytic site and mechanism. Med. Res. Rev 1995, 15 (4), 325-388.
2. Binda, C.; Newton-Vinson, P.; Hubálek, F.; Edmonson, D. E.; Mattevi, A. Structure of human monoamine oxidase B, a drug target for the treatment of neurological disorders. Nat. Struct. Biol. 2002, 9, 22-26, Data deposition: www.pdb.org (PDB ID code 1GOS). (Pubitemid 34049174)
3. De Colibus, L.; Li, M.; Binda, C.; Lustig, A.; Edmonson, D. E.; Mattevi, A. Three-dimensional structure of human monoamine oxidase A (MAO A): Relation to the structures of rat MAO A and human MAO B. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 12684-12689, Data deposition: www.pdb.org (PDB ID code 2BXR, 2BXS, and 2BYB).
4. Strolin-Benedetti, M.; Dostert, P. Monoamine oxidase: from physiology and pathophysiology to the design and clinical application of reversible inhibitors. Adv. Drug Res. 1992, 23, 65-125.
5. (a) Carreiras, M. C.; Marco, J. L. Recent approaches to novel anti-Alzheimer therapy. Curr. Pharm. Des. 2004, 10 (25), 3167-3175. (Pubitemid 39242911)
6. (b) Fernández, H. H.; Chen, J. J. Monoamine oxidase-B inhibition in the treatment of Parkinson's disease. Pharmacotherapy 2007, 27, 174S-185S. (Pubitemid 350234307)
7. (c) Factor, S. A. Current status of symptomatic medical therapy in Parkinson's disease. Neurotherapeutics 2008, 5 (2), 164-180.
8. (d) Santana, L.; Gonzaĺez-Diáz, H.; Quezada, E.; Uriarte, E.; Yańẽz, M.; Vinã, D.; Orallo, F. Quantitative Structure-Activity Relationship and Complex Network Approach to Monoamine Oxidase A and B Inhibitors. J. Med. Chem. 2008, 51 (21), 6740-6751.
9. Pacher, P.; Kecskemeti, V. Trends in the development of new antidepressant. Is there a light at the end of the tunnel? Curr. Med. Chem. 2004, 11 (7), 925-943. (Pubitemid 38425924)
10. Bolasco, A.; Fioravanti, R.; Carradori, S. Recent development of monoamine oxidase inhibitors. Expert Opin. Ther. Pat. 2005, 15 (12), 1763-1782. (Pubitemid 43056413)
11. Shih, J. C.; Chen, K.; Ridd, M. J. Monoamine oxidase: from genes to behaviour. Annu. Rev. Neurosci. 1999, 22, 197-217.
12. Mellick, G. D.; Buchanan, D. D.; McCann, S. J.; James, K. M.; Johnson, A. G.; Davis, D. R.; Liyou, N.; Chan, D.; Le Couteur, D. G. Variations in the monoamine oxidase B (MAO B) gene are associated with Parkinson's disease. Movement Disord. 1999, 14, 219-224. (Pubitemid 30011836)
13. (a) Barnham, K. J.; Masters, C. L.; Bush, A. I. Neurodegenerative diseases and oxidative stress. Nat. Rev. Drug Discovery 2004, 3, 205-214. (Pubitemid 38117047)
14. (b) Sayre, L. M.; Perry, G.; Smith, M. A. Oxidative Stress and Neurotoxicity. Chem. Res. Toxicol. 2008, 21, 172-188.
15. Youdim, M. B. H.; Fridkin, M.; Zheng, H. Novel bifunctional drugs targeting monoamine oxidase inhibition and iron chelation as an approach to neuroprotection in Parkinson's disease and other neurodegenerative diseases. J. Neural Transm. 2004, 111, 1455-1471. (Pubitemid 39468399)
16. Go, M. L.; Wu, X.; Liu, X. L. Chalcones: an update on cytotoxic and chemoprotective properties. Curr. Med. Chem. 2005, 12, 481-499. (Pubitemid 40305634)
17. Dimmock, J. R.; Elias, D. W.; Beazely, M. A.; Kandepu, N. M. Bioactivities of chalcones. Curr. Med. Chem. 1999, 6, 1125-1149
18. Batovska, D.; Parushev, St.; Slavova, A.; Bankova, V.; Tsvetkova, I.; Ninova, M.; Najdenski, H. Study on the substituents' effects of a series of synthetic chalcones against the yeast Candida albicans. Eur. J. Med. Chem. 2007, 42, 87-92. (Pubitemid 46198991)
19. Lahtchev, K. L.; Batovska, D. I.; Parushev, St. P.; Ubiyvovk, V. M.; Sibirny, A. A. Antifungal activity of chalcones: A mechanistic study using various yeast strains. Eur. J. Med. Chem. 2008, 43, 2220-2228.
20. Trivedi, J. C.; Bariwal, J. B.; Upadhyay, K. D.; Naliapara, Y. T.; Soshi, S. K.; Pannecouque, C. C.; De Clercq, E.; Shah, A. K. Improved and rapid synthesis of new coumarinyl chalcone derivatives and their antiviral activity. Tetrahedron Lett. 2007, 48, 8472-8474. (Pubitemid 350016206)
21. Tabata, K.; Motani, K.; Takayanagi, N.; Nishimura, R.; Asami, S.; Kimura, Y.; Ukiya, M.; Hasegawa, D.; Akihisa, T.; Suzuki, T. Xanthoangelol, a major chalcone constituent of Angelica keiskei, induces apoptosis in neuroblastoma and leukemia cells. Biol. Pharm. Bull. 2005, 28, 1404-1407. (Pubitemid 41379689)
22. Kimura, Y.; Baba, K. Antitumor and antimetastatic activities of Angelica keiskei roots, part 1: Isolation of an active substance, xanthoangelol. Int. J. Cancer 2003, 106, 429-437 (Pubitemid 36870408)
23. Cheng, Z. J.; Lin, C. N.; Hwang, T. L.; Teng, C. M. Broussochalcone A, a potent antioxidant and effective suppressor of inducible nitric oxide synthase in lipopolysaccharide-activated macrophages. Biochem. Pharmacol. 2001, 61, 939-946. (Pubitemid 32247382)
24. Rojas, J.; Domínguez, J. N.; Charris, J. E.; Lobo, G.; Payá, M.; Ferrandiz, M. L. Synthesis and inhibitory activity of dimethylaminochalcone derivatives on the induction of nitric oxide synthase. Eur. J. Med. Chem. 2002, 37, 699-705.
25. 6 and nitric oxide, causes apoptosis, and suppresses aberrant crypt foci development. Cancer Sci. 2004, 95, 448-453.
26. Israf, D. A.; Khaizurin, T. A.; Syhida, A.; Lajis, N. H.; Khozirah, S. Cardamonin inhibits COX and iNOS expression via inhibition of p65NF-μB nuclear translocation and Iμ-B phosphorylation in RAW 264.7 macrophage cells. Mol. Immunol. 2007, 44, 673-679. (Pubitemid 44415023)
27. Kim, Y. H.; Kim, J.; Park, H.; Kim, H. P. Anti-inflammatory Activity of the Synthetic Chalcone Derivatives: Inhibition of Inducible Nitric Oxide Synthase-Catalyzed Nitric Oxide Production from Lipopolysaccharide-Treated RAW 264.7 Cells. Biol. Pharm. Bull. 2007, 30 (8), 1450-1455. (Pubitemid 47282192)
28. Ngameni, B.; Watchueng, J.; Boyom, F. F.; Keumedjio, F.; Ngadjui, B. T.; Gut, J.; Abegaz, B. M.; Rosenthal, P. J. Antimalarial prenylated chalcones from the twigs of Dorstenia barteri var subtriangularis. ARKIVOC 2007, xiii, 116-123.
29. Santos, L.; Curi Pedrosa, R.; Correa, R.; Filho, V. C.; Nunes, R. J.; Yunes, R. A. Biological Evaluation of Chalcones and Analogues as Hypolipidemic Agents. Arch. Pharm. Chem. Life Sci. 2006, 339, 541-546. (Pubitemid 44638518)
30. Orallo, F. trans-Resveratrol: a magical elixir of eternal youth. Curr. Med. Chem. 2008, 15, 1887-1898.
31. Howitz, K. T.; Bitterman, K. J.; Cohen, H. Y.; Lamming, D. W.; Lavu, S.; Wood, J. G.; Zipkin, R. E.; Chung, P.; Kisielewski, A.; Zhang, L. L.; Scherer, B.; Sinclair, D. A. Small molecule activators of sirtuins extend Saccharomyces cerevisiae lifespan. Nature 2003, 425, 191-196. (Pubitemid 37150899)
32. (a) Haraguchi, H.; Tanaka, Y.; Kabbash, A.; Fujioka, T.; Ishizu, T.; Yagi, A. Monoamine oxidase inhibitors from Gentiana lutea. Phytochemistry 2004, 65, 2255-2260. (Pubitemid 39144381)
33. (b) Jamal, H.; Ansari, W. H.; Rizvi, S. J. Evaluation of chalcones-a flavonoid subclass for their anxiolytic effect in rats using elevated plus maze and open field behaviour tests. Fund. Clin. Pharmacol. 2008, 22, 673-681.
34. (c) Tanaka, S.; Kuwai, Y.; Tabata, M. Isolation of Monoamine Oxidase Inhibitors from Glycyrrhiza uralensis Roots and the Structure-Activity Relationship. Planta Med. 1987, 53, 5-8. (Pubitemid 17009264)
35. Chimenti, F.; Bolasco, A.; Manna, F.; Secci, D.; Chimenti, P.; Granese, A.; Befani, O.; Turini, P.; Cirilli, R.; La Torre, F.; Alcaro, S.; Ortuso, F.; Thierry, L. Synthesis, biological evaluation and 3D-QSAR of 1,3,5- trisubstituted-4,5-dihydro-(1H)-pyrazole derivatives as potent and highly selective monoamine oxidase A inhibitors. Curr. Med. Chem. 2006, 13, 1411-1428.
36. Chimenti, F.; Fioravanti, R.; Bolasco, A.; Manna, F.; Chimenti, P.; Secci, D.; Befani, O.; Turini, P.; Ortuso, F.; Alcaro, S. Monoamine Oxidase Isoform-Dependent Tautomeric Influence in the Recognition of 3,5-Diaryl Pyrazole Inhibitors. J. Med. Chem. 2007, 50, 425-428. (Pubitemid 46239776)
37. Chimenti, F.; Fioravanti, R.; Bolasco, A.; Manna, F.; Chimenti, P.; Secci, D.; Rossi, F.; Turini, P.; Ortuso, F.; Alcaro, S.; Cardia, M. C. Synthesis, molecular modeling studies and selective inhibitory activity against MAO of N1-propanoyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole derivatives. Eur. J. Med. Chem. 2008, 43, 2262-2267.
38. Yáñez, M.; Fraiz, N.; Cano, E.; Orallo, F. Inhibitory effects of cis- and trans-resveratrol on noradrenaline and 5-hydroxytryptamine uptake and on monoamine oxidase activity. Biochem. Biophys. Res. Comm. 2006, 344, 688-695.
39. Berman, H. M.; Westbrook, J.; Feng, Z.; Gilliland, G.; Bhat, T. N.; Weissig, H.; Shindyalov, I. N.; Bourne, P. E. The protein data bank. Nucleic Acids Res. 2000, 28, 235-242. (Pubitemid 30047768)
40. Son, S. Y.; Ma, J.; Kondou, Y.; Yoshimura, M.; Yamashita, E.; Tsukihara, T. Structure of human monoamine oxidase A at 2.2-Å resolution: The control of opening the entry for substrates/inhibitors. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 5739-5744, Data deposition: www.pdb.org (PDB ID code 2Z5X).
41. Hubalek, F.; Binda, C.; Khalil, A.; Li, M.; Mattevi, A.; Castagnoli, N.; Edmondson, D. E. Demonstration of Isoleucine 199 as a Structural Determinant for the Selective Inhibition of Human Monoamine Oxidase B by Specific Reversible Inhibitors. J. Biol. Chem. 2005, 280, 15761-15766, Data deposition: www.pdb.org (PDB ID code 2BK3). (Pubitemid 40616695)
42. Chimenti, F.; Maccioni, E.; Secci, D.; Bolasco, A.; Chimenti, P.; Granese, A.; Carradori, S.; Alcaro, S.; Ortuso, F.; Yańẽz, M.; Orallo, F.; Cirilli, R.; Ferretti, R.; La Torre, F. Synthesis, Stereochemical Identification, and Selective Inhibitory Activity against Human Monoamine Oxidase-B of 2-Methylcyclohexylidene-(4-arylthiazol-2-yl)hydrazones. J. Med. Chem. 2008, 51, 4874-4880.
43. Maestro, Version 4.1; Schroedinger Inc.: Portland, OR, 1998-2001.
44. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. Macromodel - an integrated software system for modeling organic and bioorganic molecules using molecular mechanics. J. Comput. Chem. 1990, 11, 440-467.
45. (a) McDonald, D. Q.; Still, W. C. AMBER torsional parameters for the peptide backbone. Tetrahedron Lett. 1992, 33, 7743-7746. (Pubitemid 23002290)
46. (b) Weiner, S. J.; Kollman, P. A.; Case, D. A.; Singh, U. C.; Chio, C.; Alagona, G.; Profeta, S.; Weiner, P. A new force field for molecular mechanical simulation of nucleic acids and proteins. J. Am. Chem. Soc. 1984, 106, 765-784. (Pubitemid 14548426)
47. Hasel, W.; Hendrickson, T. F.; Still, W. C. A rapid approximation to the solvent-accessible surface areas of atoms. Tetrahedron Comput. Methodol. 1988, 1, 103-116.
48. (a) Glide, Version 4.1;, Schroedinger Inc.: Portland, OR, 1998-2001;
49. (b) Eldridge, M. D.; Murray, C. W.; Auton, T. R.; Paolini, G. V.; Mee, R. P. Empirical scoring functions: I. The development of a fast empirical scoring function to estimate the binding affinity of ligands in receptor complexes. J. Comput.-Aided Mol. Des. 1997, 11, 425-445. (Pubitemid 127505895)