2-Benzazepine nitrones protect dopaminergic neurons against 6-hydroxydopamine-induced oxidative toxicity

Archiv der Pharmazie

Volumn 345, Issue 8, 2012, Pages 598-609

  Soto Otero, Ramõn ^a   Méndez Álvarez, Estefanía ^a   Sánchez Iglesias, Sofía ^a   Labandeira García, José Luís ^a   Rodríguez Pallares, Jannette ^a   Zubkov, Fedor I ^b   Zaytsev, Vladimir P ^b   Voskressensky, Leonid G ^b   Varlamov, Alexey V ^b   De Candia, Modesto ^c   Fiorella, Filomena ^c   Altomare, Cosimo ^c  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b PEOPLES FRIENDSHIP UNIVERSITY OF RUSSIA   (Russian Federation)

^c UNIVERSITY OF BARI   (Italy)

Author keywords

2 Benzazepine nitrones; 6 Hydroxydopamine; Cholinesterase inhibition; Dopaminergic neurons; Neuroprotection

Indexed keywords

1' BENZYL 5,5 DIMETHYL 4,5 DIHYDROSPIRO[ 2 BENZAZEPINE 3,4' PIPERIDINE] 2 OXIDE; 1' ISOPROPYL 5,5 DIMETHYL 4,5 DIHYDROSPIRO[ 2 BENZAZEPINE 3,4' PIPERIDINE] 2 OXIDE; 3,3,5,5,7 PENTAMETHYL 4,5 DIHYDRO 3H 2 BENZAZEPINE 2 OXIDE; 5 DIETHOXYPHOSPHORYL 5 METHYL 1 PYRROLINE 1 OXIDE; 5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; 5,5 DIMETHYL 2',3',4,5,5',6' HEXAHYDROSPIRO[ 2 BENZAZEPINE 3,4' PYRAN] 2 OXIDE; 5,5 DIMETHYL 4,5 DIHYDROSPIRO[ 2 BENZAZEPINE 3,1' CYCLOBUTANE] 2 OXIDE; 5,5 DIMETHYL 4,5 DIHYDROSPIRO[ 2 BENZAZEPINE 3,1' CYCLOPENTANE] 2 OXIDE; 5,5,7 TRIMETHYL 4,5 DIHYDROSPIRO[ 2 BENZAZEPINE 3,1' CYCLOHEXANE] 2 OXIDE; 5,7 DIMETHYL 4,5 DIHYDROSPIRO[ 2 BENZAZEPINE 3,1' CYCLOHEXANE] 2 OXIDE; BENZAZEPINE DERIVATIVE; CARBONYL DERIVATIVE; CHOLINESTERASE; DISUFENTON SODIUM; HYDROXYL RADICAL; N TERT BUTYL ALPHA PHENYLNITRONE; NITRONE DERIVATIVE; OXIDOPAMINE; PBN; THIOBARBITURIC ACID REACTIVE SUBSTANCE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; BRAIN MITOCHONDRION; CELL LOSS; CONTROLLED STUDY; CYTOTOXICITY; DOPAMINERGIC NERVE CELL; DRUG EFFICACY; DRUG INHIBITION; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; IN VITRO STUDY; LIPID PEROXIDATION; NERVE CELL CULTURE; NEUROPROTECTION; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL; PROTEIN CARBONYLATION; RAT; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION;

ANIMALS; BENZAZEPINES; BRAIN; CELL COUNT; CELLS, CULTURED; CHOLINESTERASE INHIBITORS; CYCLIC N-OXIDES; DISEASE MODELS, ANIMAL; DOPAMINERGIC NEURONS; INHIBITORY CONCENTRATION 50; LIPID PEROXIDATION; MITOCHONDRIA; MOLECULAR STRUCTURE; NEUROPROTECTIVE AGENTS; NITROGEN OXIDES; OXIDATIVE STRESS; OXIDOPAMINE; PARKINSON DISEASE, SECONDARY; PRIMARY CELL CULTURE; PROTEIN CARBONYLATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84864580141     PISSN: 03656233     EISSN: 15214184     Source Type: Journal    
DOI: 10.1002/ardp.201200007     Document Type: Article

References (69)

1. R. A. Floyd, R. D. Kopke, C.-H. Choi, S. B. Foster, S. Doblas, R. A. Towner, Free Radical Biol. Med. 2008, 45, 1361-1374.
2. J. L. Zweier, M. A. H. Talukder, Cardiovasc. Res. 2006, 70, 181-190.
3. E. R. Stadtman, Free Radical Res. 2006, 40, 1250-1258.
4. S. Mandel, E. Grünblatt, P. Riederer, M. Gerlach, Y. Levites, M. B. H. Youdim, CNS Drugs 2003, 17, 729-762.
5. R. A. Floyd, K. Hensley, M. J. Forster, J. A. Kelleher-Andreson, P. L. Wood, Mech. Ageing Dev. 2002, 123, 1021-1031.
6. B. Moosmann, C. Behl, Expert Opin. Invest. Drugs 2002, 11, 1407-1435.
7. K. R. Maples, A. R. Green, R. A. Floyd, CNS Drugs 2004, 18, 1071-1084.
8. C. X. Wang, A. Shuaib, Int. J. Clin. Pract. 2004, 58, 964-969.
9. L. Zuo, Y. R. Chen, L. A. Reyes, H. L. Lee, C. L. Chen, F. A. Villamena, J. L. Zweier, J. Pharmacol. Exp. Ther. 2009, 329, 515-523.
10. G. Durand, B. Poeggeler, S. Ortial, A. Polidori, F. A. Villamena, J. Bökler, R. Hardeland, M. A. Pappolla, B. Pucci, J. Med. Chem. 2010, 53, 4849-4861.
11. G. Durand, R. A. Prosak, Y. Han, S. Ortial, A. Rockenbauer, B. Pucci, F. A. Villamena, Chem. Res. Toxicol. 2009, 22, 1570-1581.
12. D. Milatovic, Z. Radic, M. Zivin, W.-D. Dettbarn, Free Radical Biol. Med. 2000, 28, 597-603.
13. D. Milatovic, M. Zivin, E. Hustedt, W.-D. Dettbarn, Neurosci. Lett. 2000, 278, 25-28.
14. M. Zivin, D. Milatovic, W.-D. Dettbarn, Brain Res. 1999, 850, 63-72.
15. C. E. Thomas, D. F. Ohlweiler, A. A. Carr, T. R. Nieduzak, D. A. Hay, G. Adams, R. Vaz, R. C. Bernotas, J. Biol. Chem. 1996, 271, 3097-3104.
16. C. E. Thomas, D. F. Ohlweiler, B. Kalyanaraman, J. Biol. Chem. 1994, 269, 28055-28061.
17. R. Soto-Otero, E. Méndez-Álvarez, S. Sánchez- Iglesias, F. I. Zubkov, L. G. Voskressensky, A. V. Varlamov, M. de Candia, C. Altomare, Biochem. Pharmacol. 2008, 75, 1526-1537.
18. S. Duty, P. Jenner, Br. J. Pharmacol. 2011, 164, 1357-1391.
19. N. Simola, M. Morelli, A. R. Carta, Neurotoxicol. Res. 2007, 11, 151-167.
20. R. Soto-Otero, E. Méndez-Álvarez, Á. Hermida-Ameijeiras, A. M. Lõpez-Real, J. L. Labandeira-García, Biochem. Pharmacol. 2002, 64, 125-135.
21. E. A. Mazzio, R. R. Reams, K. F. Soliman, Brain Res. 2004, 1004, 29-44.
22. J. Sian, D. T. Dexter, A. J. Lees, S. Daniel, Y. Agid, F. Javoy-Agid, P. Jenner, C. D. Marsden, Ann. Neurol. 1994, 36, 348-355.
23. G. Kunikowska, G. P. Jenner, Brain Res. 2001, 922, 51-64.
24. E. Oestreicher, G. J. Sengstock, P. Riederer, C. W. Olanow, A. J. Dunn, G. W. Arendash, Brain Res. 1994, 660, 8-18.
25. Y. Glinka, M. Gassen, M. B. Youdim, J. Neural Transm. Suppl. 1997, 50, 55-66.
26. Y. Y. Glinka, M. B. H. Youdim, Eur. J. Pharmacol. 1995, 292, 329-332.
27. A. Pezzella, M. d'Ischia, A. Napolitano, G. Misuraca, G. Prota, J. Med. Chem. 1997, 40, 2211-2216.
28. P. Gee, A. J. Davison, Free Radical Biol. Med. 1989, 6, 271-284.
29. L. M. Sayre, G. Perry, M. A. Smith, Chem. Res. Toxicol. 2008, 21, 172-188.
30. L. M. Sayre, G. Perry, C. S. Atwood, M. A. Smith, Cell. Mol. Biol. 2000, 46, 731-741.
31. M. Hashimoto, L. J. Hsu, Y. Xia, A. Takeda, A. Sisk, M. Sundsmo, E. Masliah, NeuroReport 1999, 10, 717-721.
32. J. N. Keller, J. Gee, Q. Ding, Ageing Res. Rev. 2002, 1, 279-293.
33. J. Choi, H. D. Rees, S. T. Weintraub, A. I. Levey, L. S. Chin, L. Li, J. Biol. Chem. 2005, 280, 11648-11655.
34. S. H. Lee, I. A. Blair, Chem. Res. Toxicol. 2000, 13, 698-720.
35. H. Esterbauer, R. J. Schaur, H. Zollner, Free Radical Biol. Med. 1991, 11, 81-128.
36. I. Delle-Donne, G. Aldini, M. Carini, R. Colombo, R. Rossi, A. Milani, J. Cell. Mol. Med. 2006, 10, 389-406.
37. A. Negre-Salvayre, C. Coatrieux, C. Ingueneau, R. Salvayre, Br. J. Pharmacol. 2008, 153, 6-20.
38. M. Shamoto-Nagai, W. Maruyama, Y. Hashizume, M. Yoshida, T. Osawa, P. Riederer, M. Naoi, J. Neural. Transm. 2007, 114, 1559-1567.
39. N. Shibata, Y. Inose, S. Toi, A. Hiroi, T. Yamamoto, M. Kobayashi, Acta Histochem. Cytochem. 2010, 43, 69-75.
40. R. J. Castellani, G. Perry, S. L. Siedlak, A. Nunomura, S. Shimohama, J. Zhang, T. Montine, L. M. Sayre, M. A. Smith, Neurosci. Lett. 2002, 319, 25-28.
41. A. Yoritaka, N. Hattori, K. Uchida, M. Tanaka, E. R. Stadtman, Y. Mizuno, Proc. Natl. Acad. Sci. USA 1996, 93, 2696-2701.
42. K. Chen, J. Maley, P. H. Yu, J. Neurochem. 2006, 99, 1413-1424.
43. S. Sánchez-Iglesias, P. Rey, E. Méndez-Álvarez, J. L. Labandeira-García, R. Soto-Otero, Neurochem. Res. 2007, 32, 99-105.
44. W. Dauer, S. Przedborski, Neuron 2003, 39, 889-909.
45. Z. I. Alam, S. E. Daniel, A. J. Lees, D. C. Marsden, P. Jenner, P. Halliwell, J. Neurochem. 1997, 69, 1326-1329.
46. D. T. Dexter, A. E. Holley, W. E. Flitter, T. F. Slater, F. R. Wells, S. E. Daniel, A. J. Lees, P. Jenner, C. D. Marsden, Mov. Disord. 1994, 9, 92-97.
47. R. Soto-Otero, E. Méndez-Álvarez, A. Hermida-Ameijeiras, A. Muñoz-Patiño, J. L. Labandeira-García, J. Neurochem. 2000, 74, 1605-1612.
48. G. N. L. Jameson, A. B. Kudryavtsev, W. Linert, J. Chem. Soc., Perkin Trans. 2 2001, 2, 557-562.
49. G. N. L. Jameson, R. F. Jameson, W. Linert, Org. Biomol. Chem. 2004, 2, 2346-2351.
50. W. Linert, E. Herlinger, R. F. Jameson, E. Kienzi, K. Jellinger, M. B. H. Youdim, Biochim. Biophys. Acta 1996, 1316, 160-168.
51. E. Méndez-Álvarez, R. Soto-Otero, A. Hermida-Ameijeiras, M. E. Lõpez-Martín, J. L. Labandeira-García, Free Radical Biol. Med. 2001, 31, 986-998.
52. R. Soto-Otero, C. Sanmartín-Suárez, S. Sánchez- Iglesias, A. Hermida-Ameijeiras, I. Sánchez-Sellero, E. Méndez-Álvarez, J. Biochem. Mol. Toxicol. 2006, 20, 209-220.
53. J. C. Barreto, G. S. Smith, N. H. Strobel, P. A. McQuillin, T. A. Miller, Life Sci. 1995, 56, PL89-96.
54. Á. Hermida-Ameijeiras, E. Méndez- Álvarez, S. Sánchez-Iglesias, C. Sanmartín-Suárez, R. Soto-Otero, Neurochem. Int. 2004, 45, 103-116.
55. T. L. Fevig, S. M. Bowen, D. A. Janowick, B. K. Jones, H. R. Munson, D. F. Ohlweiler, C. E. Thomas, J. Med. Chem. 1996, 39, 4988-4996.
56. C. E. Thomas, P. Bernardelli, S. M. Bowen, S. F. Chaney, D. Friedrich, D. A. Janowick, B. K. Jones, F. J. Keeley, J. H. Kehne, B. Ketteler, D. F. Ohlweiler, L. A. Paquette, D. J. Robke, T. L. Fevig, J. Med. Chem. 1996, 39, 4997-5004.
57. M. de Candia, P. Fossa, S. Cellamare, L. Mosti, A. Carotti, C. Altomare, Eur. J. Pharm. Sci. 2005, 26, 78-86.
58. J. Skolimowski, A. Kochman, L. Gçbicka, E. Metodiewa, Bioorg. Med. Chem. 2003, 11, 3529-3539.
59. S.-Y. Chiou, G.-W. Lai, Y.-T. Tsai, L.-Y. Lin, G. Lin, Med. Chem. Res. 2005, 14, 297-308.
60. G. L. Ellman, K. D. Courtney, V. Anres, R. M. Featherstone, Biochem. Pharmacol. 1961, 7, 88-95.
61. E. Giacobini, Int. J. Geriatr. Psychiatry 2003, 18, S1-S5.
62. Z. Rakonczay, Acta Biol. Hung. 2003, 54, 183-189.
63. T. Arendt, M. K. Brückner, M. Lange, V. Bigl, Neurochem. Int. 1992, 21, 381-396.
64. N. H. Greig, T. Utsuki, D. K. Ingram, Y. Wang, G. Pepeu, C. Scali, Q. S. Yu, J. Mamczarz, H. W. Holloway, T. Giordano, D. Chen, K. Furukawa, K. Sambamurti, A. Brossi, D. K. Lahiri, Proc. Natl. Acad. Sci. USA 2005, 102, 17213-17218.
65. A. V. Varlamov, V. V. Kouznetsov, F. I. Zubkov, A. I. Chernyshev, G. G. Alexandrov, A. R. Palma, L. Vargas, S. Salas, Synthesis 2001, 6, 849-854.
66. J. M. G. Urbina, J. C. Cortés, A. Palma, S. N. Lõpez, S. A. Zacchino, D. R. Enriz, J. C. Ribas, V. V. Kouznetzov, Bioorg. Med. Chem. 2000, 8, 691-698.
67. V. V. Kouznetsov, A. R. Palma, S. Salas, L. Y. Vargas, F. I. Zubkov, J. R. Martinez, A. V. Varlamov, J. Heterocyclic Chem. 1997, 34, 1591-1595.
68. F. I. Zubkov, J. D. Ershova, A. A. Orlova, V. P. Zaytsev, E. V. Nikitina, A. S. Peregudov, A. V. Gurbanov, R. S. Borisov, V. N. Khrustalev, A. M. Maharramov, A. V. Varlamov, Tetrahedron 2009, 65, 3789-3803.
69. M. A. K. Markwell, S. M. Haas, L. L. Bieber, N. E. Tolbert, Anal. Biochem. 1978, 87, 206-210.