Synthesis, structure, theoretical and experimental in vitro antioxidant/pharmacological properties of α-aryl, N-alkyl nitrones, as potential agents for the treatment of cerebral ischemia

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 2, 2011, Pages 951-960

  Samadi, Abdelouahid ^a   Soriano, Elena ^a   Revuelta, Julia ^a   Valderas, Carolina ^a   Chioua, Mourad ^a   Garrido, Ignacio ^b   Bartolomé, Begoña ^b   Tomassolli, Isabelle ^c   Ismaili, Lhassane ^c   González Lafuente, Laura ^d   Villarroya, Mercedes ^d   García, Antonio G ^d,e   Oset Gasque, María J ^f   Marco Contelles, José ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b INSTITUTO DE FERMENTACIONES INDUSTRIALES CSIC   (Spain)

^c UNIVERSITÉ DE FRANCHE COMTÉ   (France)

^d INSTITUTO TEÓFILO HERNANDO   (Spain)

^e HOSPITAL UNIVERSITARIO DE LA PRINCESA   (Spain)

^f UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

Antioxidant activity; Cerebral ischemia; Computational chemistry; DPPH; Hydroxyl radical; Neuroprotection; Nitrones; ORAC; Peroxyl radical; ROS; Structure; Synthesis

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; ALKYL GROUP; ALPHA (1H 3 INDOLYL) N TERT BUTYLNITRONE; ALPHA (2 BROMO 4,5 DIMETHOXYPHENYL) N TERT BUTYLNITRONE; ALPHA (2' BROMO 3 PYRIDYL) N TERT BUTYLNITRONE; ALPHA (2' BROMO 4' HYDROXY 5 METHOXYPHENYL) N BENZYLNITRONE; ALPHA (2' BROMO 4',5' DIMETHOXYPHENYL) N BENZYLNITRONE; ALPHA (2' BROMO 5' HYDROXY 4' METHOXYPHENYL) N BENZYLNITRONE; ALPHA (2' BROMO 5' HYDROXY 4' METHOXYPHENYL) N TERTBUTYLNITRONE; ALPHA (2' CHLORO 3 PYRIDYL) N TERT BUTYLNITRONE; ALPHA (4' HYDROXY 3' METHOXYPHENYL) N BENZYLNITRONE; ALPHA (4' HYDROXY 3' METHOXYPHENYL) N METHYLNITRONE; ALPHA N (5 METHOXY 1 METHYL 1H 2 INDOLYL) N TERT BUTYLNITRONE; ALPHA PHENYL N BENZYLNITRONE; ALPHA PHENYL N METHYLNITRONE; ANTIOXIDANT; BENZENE DERIVATIVE; BENZOIC ACID; HYDROXYL GROUP; HYDROXYL RADICAL; INDOLE DERIVATIVE; N TERT BUTYL ALPHA PHENYLNITRONE; NEUROPROTECTIVE AGENT; NITRONE DERIVATIVE; OLIGOMYCIN; PEROXY RADICAL; REACTIVE OXYGEN METABOLITE; ROTENONE; SCAVENGER; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; BRAIN ISCHEMIA; CALCULATION; CONTROLLED STUDY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; EXPERIMENTAL STUDY; HUMAN; HUMAN CELL; IN VITRO STUDY; IONIZATION; NEUROBLASTOMA CELL; NEUROPROTECTION; PREDICTION; THEORETICAL STUDY;

EID: 78651520949     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.11.053     Document Type: Article

References (56)

1. A.R. Green, T. Ashwood, T. Odergren, and D.M. Jackson Pharmacol. Therapeut. 100 2003 195
2. R.A. Floyd Aging Cell 5 2006 51
3. L.A. Reink, D.R. Moore, H. Sang, E.D. Janzen, and Y. Kotake Free Rad. Biol. Med. 28 2000 345
4. G.P. Novelli, P. Angiolini, R. Tani, G. Consales, and L. Bordi Free Rad. Res. Commun. 1985 321
5. S. Kuroda, R. Tsuchidate, M.-L. Smith, K.R. Maples, and B.K.J. Siesjo Cereb. Blood Metab. 19 1999 778
6. M.R. Macleod, B. van der Worp, E.S. Sena, D.W. Howells, U. Dirhagl, and G.A. Donnan Stroke 39 2008 2824
7. For a review on the chemical and pharmacological properties of heteroarylnitrones, see: S. Goldstein, and P. Lestage Curr. Med. Chem. 7 2000 1255
8. A.G. Dias, C.E.V. Santos, F.Z.G.A. Cyrino, E. Bouskela, and P.R.R. Costa Bioorg. Med. Chem. 17 2009 3995
9. W. Porcal, P. Hernández, M. González, A. Ferreira, C. Olea-Azar, H. Cerecetto, and A. Castro J. Med. Chem. 51 2008 6150
10. S. Kim, G.V.M. de A. Vilela, J. Bouajila, A.G. Dias, F.Z.G.A. Cyrino, E. Bouskela, P.R.R. Costa, and F. Nepveu Bioorg. Med. Chem. 15 2007 3572
11. G.T. Balogh, K. Vukics, A. Könczöl, A. Kis-Varga, A. Gere, and J. Fischer Bioorg. Med. Chem. Lett. 15 2005 3012
12. D.A. Becker, J.J. Ley, L. Echegoyen, and R. Alvarado J. Am. Chem. Soc. 124 2002 4678
13. A. Dhainaut, A. Tizot, E. Raimbaud, B. Lockhart, P. Lestage, and S. Goldstein J. Med. Chem. 43 2000 2165
14. H. Nakagawa, R. Ohyama, A. Kimata, T. Suzuki, and N. Miyata Bioorg. Med. Chem. Lett. 16 2006 5939
15. B. Lalynaraman, J. Joseph, and S. Parthasarathy FEBS Lett. 280 1991 17
16. H.A.O. Hill, and P. Thornalley Biochem. Biophys. Acta 762 1983 44
17. I. Magaill, M. Plotkine, and D. Lerouet Free Radical Biol. Med. 39 2005 429
18. K. Hensley, J.M. Corney, C.A. Stewart, T. Tabatabaie, Q. Pye, and R.A. Floyd Neuroprotect. Agents Cereb. Ischemia 40 1997 299
19. W. Chamulitrat, C.E. Parker, K.B. Tomer, and R.P. Mason Free Radical Res. 23 1995 1
20. S. Chandrasekhar, R.N. Reddy, and Y.S. Rao Tetrahedron 62 2006 12098
21. C. Rodríguez, A.G. García, and J. Marco-Contelles J. Chem. Res. 2006 698
22. S.R. Byeon, Y.J. Jin, S.J. Lim, J.H. Lee, K.H. Yoo, K.J. Shin, S.J. Oh, and D.J. Kim Bioorg. Med. Chem. Lett. 17 2007 4022
23. C. Férnández-García, J.L. Marco, and E.F. Álvarez Tetrahedron 48 1992 6917
24. D. Coowar, J. Bouissac, M. Hanbali, M. Paschaki, E. Mohier, and B. Luu J. Med. Chem. 47 2004 6270
25. M.A. Andrade, M.T. Barros, and R.C. Pinto Tetrahedron 64 2008 10521
26. R.D. Hinton, and E.G. Janzen J. Org. Chem. 57 1992 2646
27. E. Colacino, N. Pierrick, F.M. Colacino, J. Martínez, and F. Lamaty Tetrahedron 64 2008 5569
28. M.C. Foti, C. Daquino, and C.J. Geraci Org. Chem. 69 2004 5888
29. M. Musialik, and G. Litwinienko Org. Lett. 7 2005 4951
30. P. Molyneaux J. Sci. Technol. 26 2004 211
31. A.K. Tuba, and G. Ilhami Chem. Biol. Interact. 174 2008 27
32. G. Cao, H. Alessio, and R. Culter Free Radical Biol. Med. 14 1993 303
33. B. Ou, M. Hampsch-Woodill, and R.L. Prior J. Agric. Food Chem. 49 2010 4619
34. A. Dávalos, C. Gómez-Cordobés, and B. Bartolomé J. Agric. Food Chem. 52 2004 48
35. J.M.C. Gutteridge Biochem. J. 243 1987 709
36. S.K. Chung, T. Ogawa, and S. Kawashiki Biosci. Biotechnol. Biochem. 61 1997 118
37. W. Kliegel, J. Metge, S.J. Rettig, and J. Trotter Can. J. Chem. 75 1997 1830
38. E. Klein, and V. Lukeš J. Phys. Chem. A 110 2006 12312
39. F.A. Villamena, C.M. Hadad, and J.L. Zweier J. Phys. Chem. A 109 2005 1662
40. F.A. Villamena, C.M. Hadad, and J.L. Zweier J. Phys. Chem. A 107 2003 4407
41. F.A. Villamena, C.M. Hadad, and J.L. Zweier J. Am. Chem. Soc. 126 2004 1816
42. M.D. Rivero-Pérez, P. Muñiz, and M.L. González-San José J. Agric. Food Chem. 5 2007 5476
43. F.A. Villamena, J.K. Merle, C.M. Hadad, and J.L. Zweier J. Phys. Chem. A 111 2007 9995
44. ChemSilico LLC, Tewksbury, MA 01876.
45. I.V. Tetko, J. Gasteiger, R. Todeschini, A. Mauri, D. Livingstone, P. Ertl, V.A. Palyulin, E.V. Radchenko, N.S. Zefirov, A.S. Makarenko, V.Y. Tanchuk, and V.V. Prokopenko J. Comput. Aided Mol. Des. 19 2005 4531
46. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P. Feeney J. Adv. Drug Delivery Rev. 23 1997 3
47. J. Egea, A.O. Rosa, A. Cuadrado, A.G. García, and M.G. López J. Neurochem. 102 2007 1842
48. F. Denizot, and R. Lang J. Immunol. Methods 89 1986 271
49. N. Cañas, T. Valero, M. Villarroya, E. Montell, J. Vergés, A.G. García, and M.G. López J. Pharmacol. Exp. Ther. 323 2007 946
50. It is worth to point out that all the nitrones studied in this work are stable in the solvents used. We thank one of referees for comments on this regard.
51. It is well known that the low stability was in the origin of the failure of the clinical assays on PBN. Thus, in our case, it is important to highlight that in the experimental conditions of the antioxidant assays (see Section 4), the new nitrones were stable in the solvents used. We thank one the reviewers for attracting our attention to this point.
52. M.J.y col. Frisch Gaussian03, Revision B.03 2003 Gaussian Pittsburg, PA
53. C. Lee, W. Yang, and R. Parr Phys. Rev. B 37 1988 785
54. A. Becke J. Chem. Phys. 98 1993 5648
55. A.E. Reed, and F. Weinhold J. Chem. Phys. 78 1983 4066
56. A.E. Reed, L.A. Curtiss, and F. Weinhold Chem. Rev. 88 1988 899