Simplified bicyclic pyridinol analogues protect mitochondrial function

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 11, 2012, Pages 3584-3595

  Cai, Xiaoqing ^a   Khdour, Omar M ^a   Jaruvangsanti, Jennifer ^a   Hecht, Sidney M ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

Author keywords

Bicyclic pyridinol antioxidant; Lipid peroxidation; Mitochondrial dysfunction; Mitochondrial membrane potential; Reactive oxygen species

Indexed keywords

1,4 DIMETHYL 6 HEXADECYL 2,3 DIHYDRO 1H PYRROLO[2,3 B]PYRIDIN 5 OL; 1,4 DIMETHYL 6 HEXADECYL 2,3 DIHYDRO 1H PYRROLO[2,3 B]PYRIDIN 5 YL ACETATE; 1,4 DIMETHYL 6 HEXADECYL 2,3 DIHYDRO 1H PYRROLO[2,3 B]PYRIDINE; 1,4 DIMETHYL 6 PENTYL 2,3 DIHYDRO 1H PYRROLO[2,3 B]PYRIDINE; 1,4 DIMETHYL 6 PENTYL 2,3 DIHYDRO 1H PYRROLO[2,3 B]PYRIDINE 5 OL; 1,4 DIMETHYL 6 PENTYL 2,3 DIHYDRO 1H PYRROLO[2,3 B]PYRIDINYL ACETATE; 1,4,6 TRIMETHYL 2,3 DIHYDRO 1H PYRROLO[2,3 B]PYRIDINE; 5 BROMO 1,4 DIMETHYL 6 HEXADECYL 2,3 DIHYDRO 1H PYRROLO[2,3 B]PYRIDINE; 5 BROMO 1,4 DIMETHYL 6 PENTYL 2,3 DIHYDRO 1H PYRROLO[2,3 B]PYRIDINE; 6 DECYL 1,4 DIMETHYL 2,3 DIHYDRO 1H PYRROLO[2,3 B]PYRIDIN 5 OL; 6 DECYL 1,4 DIMETHYL 6 PENTYL 2,3 DIHYDRO 1H PYRROLO[2,3 B]PYRIDIN 5 YL ACETATE; 6 DECYL 1,4 DIMETHYL 6 PENTYL 2,3 DIHYDRO 1H PYRROLO[2,3 B]PYRIDINE; ACETATE ESTER DERIVATIVE; ALKYL GROUP; ALPHA TOCOPHEROL; ANTIOXIDANT; BICYCLIC PYRIDINOL DERIVATIVE; ESTER DERIVATIVE; METHYL GROUP; TOCOPHEROL DERIVATIVE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CELL FUNCTION; CELL PROTECTION; CELL STRESS; CHEMICAL REACTION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; MITOCHONDRION; OXIDATIVE STRESS; REGIOSELECTIVE METALATION;

ALPHA-TOCOPHEROL; ANTIOXIDANTS; CELL LINE, TUMOR; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; HUMANS; LEUKEMIA; LIPID PEROXIDATION; MEMBRANE POTENTIAL, MITOCHONDRIAL; MITOCHONDRIA; ORGANIC CHEMISTRY PROCESSES; OXIDATIVE STRESS; PYRIDINES; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84861192431     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.03.075     Document Type: Article

References (47)

1. B. Chance, H. Sies, and A. Boveris Physiol. Rev. 59 1979 527
2. E.L. Stadtman Free Radical Res. 40 2006 1250
3. W. Dröge Physiol. Rev. 82 2002 47
4. M. Valko, D. Leibfritz, J. Moncol, M.T.D. Cronin, M. Mazur, and J. Telser Int. J. Biochem. Cell Biol. 39 2007 44
5. T. Finkel Curr. Opin. Cell Biol. 15 2003 247
6. T. Finkel, M. Serrano, and M.A. Blasco Nature 448 2007 767
7. K.J. Barnham, C.L. Masters, and A.I. Bush Nat. Rev. Drug Discovery 3 2004 205
8. I.G. Kirkinezos, and C.T. Moraes Semin. Cell Dev. Biol. 12 2001 449
9. Y. Zhang, O. Marcillat, C. Giulivi, L. Ernster, and K.J.A. Davies J. Biol. Chem. 265 1990 16330
10. G.W. Burton, and K.U. Ingold Acc. Chem. Res. 19 1986 194
11. M. Wijtmans, D.A. Pratt, L. Valgimigli, G.A. DiLabio, G.F. Pedulli, and N.A. Porter Angew. Chem., Int. Ed. 42 2003 4370
12. M. Wijtmans, D.A. Pratt, J. Brikhorst, R. Serwa, L. Valgimigli, G.F. Pedulli, and N.A. Porter J. Org. Chem. 69 2004 9215
13. T.-G. Nam, C.L. Rector, H.-Y. Kim, A.F.-P. Sonnen, R. Meyer, W.M. Nau, J. Atkinson, J. Rintoul, D.A. Pratt, and N.A. Porter J. Am. Chem. Soc. 129 2007 10211
14. R. Serwa, T.-G. Nam, L. Valgimigli, S. Culbertson, C.L. Rector, B.-S. Jeong, D.A. Pratt, and N.A. Porter Chem. Eur. J. 16 2010 14106
15. T.-G. Nam, J.-M. Ku, H.-G. Park, N.A. Porter, and B.-S. Jeong Org. Biomol. Chem. 9 2011 1749
16. J. Lu, O.K. Khdour, J.S. Armstrong, and S.M. Hecht Bioorg. Med. Chem. 18 2010 7628
17. O.M. Khdour, J. Lu, and S.M. Hecht Pharm. Res. 28 2011 2896
18. E. Niki, A. Kawakami, M. Saito, Y. Yamamoto, J. Tsuchiya, and Y. Kamiya J. Biol. Chem. 260 1985 2191
19. P.P. Constantinides, A. Tustian, and D.R. Kessler Adv. Drug Deliv. Rev. 56 2004 1243
20. G.W. Burton, and K.U. Ingold Science 224 1984 569
21. J. Lu, X. Cai, and S.M. Hecht Org. Lett. 12 2010 5189
22. H. Murase, J.-H. Moon, R. Yamauchi, K. Kato, T. Kunieda, T. Yoshikawa, and J. Terao Free Radical Biol. Med. 24 1998 217
23. D.A. Pratt, G.A. DiLabio, G. Brigati, G.F. Pedulli, and L. Valgimigli J. Am. Chem. Soc. 123 2001 4625
24. L. Valgimigli, G. Brigati, G.F. Pedulli, G.A. DiLabio, M. Mastragostino, C. Arbizzani, and D.A. Pratt Chem. Eur. J. 9 2003 4997
25. L.J. McBride, R. Kierzek, S.L. Beaucage, and M.H. Caruthers J. Am. Chem. Soc. 108 1986 2040
26. Y. Gao, Q. Zhang, and J. Xu Synth. Commun. 34 2004 909
27. K.U. Ingold, G.W. Burton, D.O. Foster, M. Zuker, L. Hughes, S. Lacelle, E. Lusztyk, and M. Slaby FEBS Lett. 205 1986 117
28. L. Iuliano, J.Z. Pedersen, C. Camastra, V. Bello, S. Ceccarelli, and F. Violi Free Radical Biol. Med. 26 1999 858
29. S. Manfredini, S. Vertuani, B. Manfredi, G. Rossoni, G. Calviello, and P. Palozza Bioorg. Med. Chem. 8 2000 2791
30. P. Palozza, R. Simone, N. Picci, L. Buzzoni, N. Ciliberti, A. Natangelo, S. Manfredini, and S. Vertuani Free Radical Biol. Med. 44 2008 1452
31. Y.L. Chua, D. Zhang, U. Boelsterli, P.K. Moore, M. Whiteman, and J.S. Armstrong Biochem. Biophys. Res. Commun. 337 2005 375
32. C. Lu, and J.S. Armstrong Biochem. Biophys. Res. Commun. 363 2007 572
33. D. Zhang, C. Lu, M. Whiteman, B. Chance, and J.S. Armstrong J. Biol. Chem. 283 2008 3476
34. M.A. Tirmenstein, F.A. Nicholls-Grzemski, J.G. Zhang, and M.W. Fariss Chem. Biol. Interact. 127 2000 201
35. C.P. LeBel, H. Ishiropoulos, and S.C. Bondy Chem. Res. Toxicol. 5 1992 227
36. M.G. Bonini, C. Rota, A. Tomasi, and R.P. Mason Free Radical Biol. Med. 40 2006 968
37. M. Karlsson, T. Kurz, U.T. Brunk, S.E. Nilsson, and C.I. Frennesson Biochem. J. 428 2010 183
38. W.O. Carter, P.K. Narayanan, and J.P. Robinson J. Leuk. Biol. 55 1994 253
39. P. Ubezio, and F. Civoli Free Radical Biol. Med. 16 1994 509
40. E.H.W. Pap, G.P. Drummen, V.J. Winter, T.W.A. Kooij, P.J. Rijken, K.W.A. Wirtz, J.A. Op den Kamp, W.J. Hage, and J.A. Post FEBS Lett. 453 1999 278
41. G.P. Drummen, L.C. van Liebergen, J.A. Op den Kamp, and J.A. Post Free Radical Biol. Med. 33 2002 473
42. P. Bernardi, V. Petronilli, F. Di Lisa, and M. Forte Trends Biochem. Sci. 26 2001 112
43. P.M. Arce, O.M. Khdour, R. Goldschmidt, J.S. Armstrong, and S.M. Hecht ACS Med. Chem. Lett. 2 2011 608
44. B. Ehrenberg, V. Montana, M.D. Wei, J.P. Wuskell, and L.M. Loew Biophys. J. 53 1988 785
45. S.A. Altman, L. Randers, and G. Rao Biotechnol. Prog. 9 1993 671
46. R. Meier, T. Tomizaki, C. Schulze-Briese, U. Baumann, and A. Stocker J. Mol. Biol. 331 2003 725
47. P. Jotwani, J. Singh, and N. Anand Indian J. Chem. 27B 1988 166