Design, synthesis, and biological characterization of potential antiatherogenic nitric oxide releasing tocopherol analogs

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 20, 2005, Pages 5787-5796

  López, Gloria V ^a,c   Batthyány, Carlos ^b,c   Blanco, Fabiana ^b,c   Botti, Horacio ^b,c   Trostchansky, Andrés ^b,c   Migliaro, Eduardo ^b,c   Radi, Rafael ^b,c   González, Mercedes ^a   Cerecetto, Hugo ^a   Rubbo, Homero ^b,c  

^a UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

^b UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

^c DEPARTAMENTO DE BIOQUÍMICA   (Uruguay)

Author keywords

Antioxidant; LDL oxidation; NO donor; Vitamin E

Indexed keywords

2,5,7,8 TETRAMETHYL 2 (2 NITROOXYETHYLCARBAMOYL)CHROMAN 6 YLACETATE; 2,5,7,8 TETRAMETHYL 2 (4,8,12 TRIMETHYLTRIDECYL)CHROMAN 6 YL 2 NITROOXYACETATE; 3 (3 PHENYLSULFONYL 1,2,5 OXADIAZOLE 4 OXYL)PROPYL 6 ACETYLOXY 2,5,7,8 TETRAMETHYLCHROMAN 2 CARBOXYLATE; 3 (3 PHENYLSULFONYL N 2 OXIDE 1,2,5 OXADIAZOLE 4 OXYL)PROPYL 6 ACETYLOXY 2,5,7,8 TETRAMETHYLCHROMAN 2 CARBOXYLATE; 3 NITROOXYPROPYL 6 ACETOXY 2,5,7,8 TETRAMETHYLCHROMAN 2 CARBOXYLATE; 5 NITROOXYMETHYL 2,7,8 TRIMETHYL 2 (4,8,12 TRIMETHYLTRIDECYL)CHROMAN 6 YLACETATE; 6 ACETYLOXY 2,5,7,8 TETRAMETHYL N [2 (3 PHENYSULFONYL N 2 OXIDE 1,2,5 OXADIAZOLE 4 OXYL)ETHYL]CHROMAN 2 CARBOXAMIDE; LOW DENSITY LIPOPROTEIN; NITRIC OXIDE DONOR; TOCOPHEROL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATHEROGENESIS; DRUG ACTIVITY; DRUG DESIGN; DRUG SYNTHESIS; IN VITRO STUDY; LIPID OXIDATION; THROMBOCYTE; VASODILATATION;

ANIMALS; ANTIOXIDANTS; ATHEROSCLEROSIS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; NITRIC OXIDE; NITRIC OXIDE DONORS; RATS; RATS, WISTAR; SPECTROPHOTOMETRY, INFRARED; TOCOPHEROLS; VASODILATOR AGENTS;

EID: 24344503748     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.05.060     Document Type: Article

References (49)

1. M.N. Diaz, B. Frei, J.A. Vita, and J.F. Keaney N. Engl. J. Med. 337 1997 408
2. R. Ross E. Braunwald Heart disease: a textbook of cardiovascular medicine Vol. 1 1996 Saunders-Division of Harcourt Brace & Company Philadelphia 1105 1125
3. J.R. Hessler, D.W. Morel, L.J. Lewis, and G.M. Chisolm Atherosclerosis 3 1983 215
4. D.W. Morel, J.R. Hessler, and G.M. Chisolm J. Lipid Res. 24 1983 1070
5. D.W. Morel, P.E. DiCorleto, and G.M. Chisolm Atherosclerosis 4 1984 357
6. D. Steinberg, and J.L. Witztum Circulation 105 2002 2107
7. J.M. Rapola, J. Virtamo, J.K. Auca, O.P. Heinonen, D. Albanes, P.R. Taylor, and J.K. Huttunen JAMA 275 1996 693
8. G. de Gaetano Lancet 357 2001 89
9. J.T. Salonen, K. Nyyssonen, R. Salonen, H.M. Lakka, J. Kaikkonen, E. Porkkala-Sarataho, S. Voutilainen, T.A. Lakka, T. Rissanen, L. Leskinen, T.P. Tuomainen, V.P. Valkonen, U. Ristonmaa, and H.E. Poulsen J. Intern. Med. 248 2000 377
10. N.G. Stephens, A. Parsons, P.M. Schofield, F. Kelly, K. Cheeseman, and M.J. Mitchinson Lancet 347 1996 781
11. M. Boaz, S. Smetana, T. Weinstein, Z. Matas, U. Gafter, A. Iaina, A. Knecht, Y. Weissgarten, D. Brunner, M. Fainaru, and M.S. Green Lancet 356 2000 1213
12. R. Marchioli Lancet 354 1999 447
13. S. Yusuf, G. Dagenais, J. Pogue, J. Bosch, and P. Sleight N. Engl. J. Med. 342 2000 154
14. K. Ouahchi, M. Arita, H. Kayden, F. Hentati, M. Ben Hamida, R. Sokol, H. Arai, K. Inoue, J.L. Mandel, and M. Koenig Nat. Genet. 9 1995 141
15. L. Cavalier, K. Ouahchi, H.J. Kayden, S. Di Donato, L. Reutenauer, J.L. Mandel, and M. Koenig Am. J. Hum. Genet. 62 1998 301
16. C. Cena, D. Boschi, G.C. Tron, K. Chegaev, L. Lazzarato, A. Ditilo, M. Aragno, R. Fruttero, and A. Gasco Bioorg. Med. Chem. Lett. 14 2004 5971
17. N. Hogg, B. Kalyanaraman, J. Joseph, A. Struck, and S. Pathasarathy FEBS Lett. 334 1993 170
18. S.P.A. Goss, N. Hogg, and B. Kalyanaraman Chem. Res. Toxicol. 8 1995 800
19. N. Hogg, A. Struck, S.P.A. Goss, N. Santanam, J. Joseph, S. Parthasarathy, and B. Kalyanaraman J. Lipid Res. 36 1995 1756
20. A.T. Struck, N. Hogg, J.P. Thomas, and B. Kalyanaraman FEBS Lett. 361 1995 291
21. H. Rubbo, R. Raddi, M. Trujillo, R. Telleri, B. Kalyanaramen, S. Barnes, M. Kirk, and B.A. Freeman J. Biol. Chem. 269 1994 26066
22. H. Rubbo, S. Parthasarathy, S. Barnes, M. Kirk, B. Kalyanaraman, and B.A. Freeman Arch. Biochem. Biophys. 324 1995 15
23. A. Denicola, C. Batthyány, E. Lissi, B.A. Freeman, H. Rubbo, and R. Radi J. Biol. Chem. 277 1995 932
24. M. Moller, H. Botti, C. Batthyány, H. Rubbo, R. Radi, and A. Denicola J. Biol.Chem. 280 2005 8850
25. H. Rubbo, R. Radi, D. Anselmi, M. Kirk, S. Barnes, J. Butler, J.P. Eiserich, and B.A. Freeman J. Biol. Chem. 275 2000 10812
26. A. Trostchansky, C. Batthyany, H. Botti, R. Radi, A. Denicola, and H. Rubbo Arch. Biochem. Biophys. 395 2001 225
27. A. Trostchansky, G. Ferrer-Sueta, C. Batthyany, H. Botti, I. Batinic-Haberle, R. Radi, and H. Rubbo Free Radic. Biol. Med. 35 2003 1293
28. S.M. Sanguinetti, C. Batthyany, A. Trostchansky, H. Botti, G.I. Lopez, R.L. Wikinski, H. Rubbo, and L.E. Schreier Arch. Biochem. Biophys. 423 2004 302
29. H. Botti, C. Batthyany, A. Trostchansky, R. Radi, B.A. Freeman, and H. Rubbo Free Radic. Biol. Med. 36 2004 152
30. P.G. Wang, M.X. Xiaoping Tang, X. Wu, T. Cai, and A.J. Janczuk Chem. Rev. 102 2002 1091
31. H. Cerecetto, and W. Porcal Mini Rev. Med. Chem. 5 2005 57
32. M. Feelisch, S. Schönafinger, and E. Noack Biochem. Pharmacol. 43 1992 1281
33. C. Medana, G. Ermondi, R. Fruttero, A. Di Stilo, C. Ferretti, and A. Gasco J. Med. Chem. 37 1994 4412
34. S. Witkowski, and P. Walejko Bull. Pol. Acad. Sc. Chem. 46 1998 349
35. Scaramuzzino, G. WO 03094923, 2003; Chem. Abstr. 2003, 139, 386419.
36. 4S) C, H, S.
37. J.M. Behan, F.M. Dean, and R.A.W. Johnstone Tetrahedron 32 1976 167
38. T. Rosenau, and W.D. Habicher Tetrahedron 51 1995 7919
39. M. Feelisch, and E.A. Noack Eur. J. Pharmacol. 139 1987 19
40. G. Roma, M. Di Braccio, A. Carrieri, G. Grossi, G. Leoncini, M.G. Signorello, and A. Carotti Bioorg. Med. Chem. 11 2003 123
41. Q.H. Gibson, and F.J. Roughton J. Physiol. 136 1957 507
42. B.T. Mellion, L.J. Ignarro, E.H. Ohlstein, E.G. Pontecorvo, A.L. Hyman, and P.J. Kadowitz Blood 57 1981 946
43. V.B. O'Donnell, P.H. Chumley, N. Hogg, A. Bloodsworth, V.M. Darley-Usmar, and B.A. Freeman Biochemistry 36 1997 15216
44. Y. Kawashima, T. Ikemoto, A. Horiguchi, M. Hayashi, K. Matsumoto, K. Kawarasaki, R. Yamazaki, S. Okuyama, and K. Hatayama J. Med. Chem. 36 1993 815
45. W.V. Farrar J. Chem. Soc. 1964 904
46. A. Monge, A. López de Ceráin, O. Ezpeleta, H. Cerecetto, E. Dias, R. Di Maio, M. González, S. Onetto, G. Seoane, L. Suescun, and R. Mariezcurrena Pharmazie 53 1998 758
47. M.L. Lolli, C. Cena, C. Medana, L. Lazzarato, G. Morini, G. Coruzzi, S. Namarini, R. Fruttero, and A. Gasco J. Med. Chem. 44 2001 3463
48. G. Sorba, C. Medana, R. Fruttero, C. Cena, A. Di Stilo, U. Galli, and A. Gasco J. Med. Chem. 40 1997 463
49. C. Batthyány, C.X. Santos, H. Botti, C. Cervenansky, R. Radi, O. Augusto, and H. Rubbo Arch. Biochem. Biophys. 384 2000 335