A strategy for suppressing redox stress within mitochondria

ACS Medicinal Chemistry Letters

Volumn 2, Issue 8, 2011, Pages 608-613

  Arce, Pablo M ^a   Khdour, Omar M ^a   Goldschmidt, Ruth ^a   Armstrong, Jeffrey S ^a   Hecht, Sidney M ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

Author keywords

electron transport chain; lipid peroxidation; mitochondria; Reactive oxygen species

Indexed keywords

ALPHA TOCOPHEROL; ANTIOXIDANT; IDEBENOL; IDEBENONE; IDEBENONE DERIVATIVE; NEUROPROTECTIVE AGENT; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG EFFICACY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; FIBROBLAST CULTURE; FRIEDREICH ATAXIA; LEUKEMIA CELL; LIPID PEROXIDATION; MITOCHONDRION; NEUROPROTECTION; OXIDATIVE STRESS; PRIORITY JOURNAL; REDOX STRESS;

EID: 80051762873     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml200095w     Document Type: Article

References (39)

1. Saraste, M. W. Oxidative phosphorylation at the fin de siècle Science 1999, 283, 1488-1493
2. Newmeyer, D. D.; Ferguson-Miller, S. Mitochondria: Releasing power for life and unleashing the machineries of death Cell 2003, 112, 481-490 (Pubitemid 36263081)
3. Markesbery, W. R.; Carney, J. M. Oxidative alterations in Alzheimer's disease Brain Pathol. 1999, 9, 133-146 (Pubitemid 29056524)
4. Calabrese, V.; Lodi, R.; Tonon, C.; D'Agata, V.; Sapienza, M.; Scapagnini, G.; Mangiameli, A.; Pennisi, G.; Stella, A. M.; Butterfield, D. A. Oxidative stress, mitochondrial dysfunction and cellular stress response in Friedreich's ataxia J. Neurol. Sci. 2005, 233, 145-162 (Pubitemid 40812334)
5. Lin, M. T.; Beal, M. F. Mitochondrial dysfunction and oxidative stress in neurodegenerative diseases Nature 2006, 443, 787-795 (Pubitemid 44622683)
6. DiMauro, S.; Schon, E. A. Mitochondrial disorders in the nervous system Annu. Rev. Neurosci. 2008, 31, 91-123
7. Armstrong, J. S.; Khdour, O. M.; Hecht, S. M. Does oxidative stress contribute to the pathology of Friedreich's ataxia? A radical question FASEB J. 2010, 24, 2152-2163
8. Mates, J. M.; Perez-Gomez, C.; Nunez de Castro, I. Antioxidant enzymes and human diseases Clin. Biochem. 1999, 32, 595-603 (Pubitemid 30039087)
9. Fridovich, I. Fundamental aspects of reactive oxygen species, or what's the matter with oxygen? Ann. N. Y. Acad. Sci. 1999, 893, 13-18 (Pubitemid 30038064)
10. Lenaz, G. Role of mitochondria in oxidative stress and aging Biochim. Biophys. Acta 1998, 1366, 53-67 (Pubitemid 28467022)
11. Orrenius, S.; Gogvadze, V.; Zhivotovsky, B. Mitochondrial oxidative stress: Implications for cell death Annu. Rev. Pharmacol. Toxicol. 2007, 47, 143-183
12. Mordente, A.; Martorana, G. E.; Minotti, G.; Giardina, B. Antioxidant properties of 2,3-dimethoxy-5-methyl-6-(10-hydroxydecyl)-1,4-benzoquinone (idebenone) Chem. Res. Toxicol. 1998, 11, 54-63
13. Ikejiri, Y.; Mori, E.; Ishii, K.; Nishimoto, K.; Yasuda, M.; Sasaki, M. Idebenone improves cerebral mitochondrial oxidative metabolism in a patient with MELAS Neurology 1996, 47, 583-585 (Pubitemid 26324069)
14. Di Prospero, N. A.; Baker, A.; Jeffries, N.; Fischbeck, K. H. Neurological effects of high-dose idebenone in patients with Friedreich's ataxia: A randomized, placebo-controlled trial Lancet Neurol. 2007, 6, 878-886 (Pubitemid 47404985)
15. Tonon, C.; Lodi, R. Idebenone in Friedreich's ataxia Expert Opin. Pharmacother. 2008, 9, 2327-2337
16. Duveau, D. Y.; Arce, P. M.; Schoenfeld, R. A.; Raghav, N.; Cortopassi, G. A.; Hecht, S. M. Synthesis and characterization of mitoQ and idebenone analogues as mediators of oxygen consumption in mitochondria Bioorg. Med. Chem. 2010, 18, 6429-6441
17. Lu, J.; Khdour, O. M.; Armstrong, J. S.; Hecht, S. M. Design, synthesis, and evaluation of an α-tocopherol analogue as a mitochondrial antioxidant Bioorg. Med. Chem. 2010, 18, 7628-7638
18. Tallman, K. A.; Pratt, D. A.; Porter, N. A. Kinetic products of linoleate peroxidation: Rapid β-fragmentation of nonconjugated peroxyls J. Am. Chem. Soc. 2001, 123, 11827-11828 (Pubitemid 33121815)
19. Wijtmans, M.; Pratt, D. A.; Valgimigli, L.; DiLabio, G. A.; Pedulli, G. F.; Porter, N. A. 6-Amino-3-pyridinols: Towards diffusion-controlled chain-breaking antioxidants Angew. Chem., Int. Ed. 2003, 42, 4370-4373 (Pubitemid 37221321)
20. Witjtmans, M.; Pratt, D. A.; Brinkhorst, J.; Serwa, R.; Valgimigli, L.; Pelludi, G. F.; Porter, N. A. Synthesis and reactivity of some 6-substituted-2,4-dimethyl-3-pyridinols, a novel class of chain breaking antioxidants J. Org. Chem. 2004, 69, 9215-9223 (Pubitemid 40004045)
21. Valgimigli, L.; Brigati, G.; Pelludi, G. F.; DiLabio, G. A.; Mastragostino, M.; Arbizzani, C.; Pratt, D. A. The effect of ring nitrogen atoms on the homolytic reactivity of phenolic compounds: Understanding the radical-scavenging ability of 5-pyrimidinols Chem.-Eur. J. 2003, 9, 4997-5010
22. Nara, S. J.; Jha, M.; Brinkhorst, J.; Zemanek, T. J.; Pratt, D. A. A simple Cu-catalyzed coupling approach to substituted 3-pyridinol and 5-pyrimidinol antioxidants J. Org. Chem. 2008, 73, 9326-9333
23. Anderson, K. W.; Ikawa, T.; Tundel, R. E.; Buchwald, S. L. The selective reaction of aryl halides with KOH: Synthesis of phenols, aromatic ethers, and benzofurans J. Am. Chem. Soc. 2006, 128, 10694-10695 (Pubitemid 44277754)
24. Kaiser, E. M. Lateral metalation of methylated nitrogenous heterocycles Tetrahedron 1983, 39, 2055-2064
25. 581/591, an oxidation-sensitive fluorescent lipid peroxidation probe: (micro)spectroscopic characterization and validation of methodology Free Radical Biol. Med. 2002, 33, 473-490 (Pubitemid 34874969)
26. Wills, D. Lipid peroxide formation in microsomes. General considerations Biochem. J. 1969, 113, 315-324
27. Mellores, A.; Tappel, A. L. The inhibition of mitochondrial peroxidation by ubiquinone and ubiquinol J. Biol. Chem. 1966, 241, 4353-4356
28. Suno, M.; Nagaoka, A. Inhibition of lipid peroxidation by idebenone in brain mitochondria in the presence of succinate Arch. Gerontol. Geriatr. 1989, 8, 291-297 (Pubitemid 19125295)
29. Miccadei, S.; Kyle, M. E.; Gilfor, D.; Farber, J. L. Toxic consequence of the abrupt depletion of glutathione in cultured rat hepatocytes Arch. Biochem. Biophys. 1988, 265, 311-320
30. Tirmenstein, M. A.; Nicholls-Grzemski, F. A.; Zhang, J.-G.; Fariss, M. W. Glutathione depletion and the production of reactive oxygen species in isolated hepatocyte suspensions Chem.-Biol. Interact. 2000, 127, 201-217 (Pubitemid 30624156)
31. 10 analog decylubiquinone inhibits the redox-activated mitochondrial permeability transition. Role of mitochondrial respiratory complex III.J. Biol. Chem. 2003, 278, 49079-49084
32. Campo, M. L.; Kinnally, K. W.; Tedeschi, H. The effect of antimycin A on mouse liver inner mitochondrial membrane channel activity J. Biol. Chem. 1992, 267, 8123-8127
33. Balaban, R. S.; Nemoto, S.; Finkel, T. Mitochondria, oxidants, and aging Cell 2005, 120, 483-495 (Pubitemid 40269763)
34. Piskernik, C.; Hainl, S.; Behling, T.; Gerald, Z.; Kehrer, I.; Redl, H. V.; Kozlov, A. Antimycin A and lipopolysaccharide cause the leakage of superoxide radicals from rat liver mitochondria Biochim. Biophys. Acta 2008, 1782, 280-285
35. Benov, L.; Sztejnberg, L.; Fridovich, I. Critical evaluation of the use of hydroethidine as a measure of superoxide anion radical Free Radical Biol. Med. 1998, 25, 826-831 (Pubitemid 28512535)
36. Griffith, O. W.; Meister, A. Potent and specific inhibition of glutathione synthesis by buthionine sulfoximine (S-n -butyl homocysteine sulfoximine) J. Biol. Chem. 1979, 254, 7558-7560 (Pubitemid 10230219)
37. Markovits, J.; Roques, B. P.; Le Pecq, J. B. Ethidium dimer: A new reagent for the fluorimetric determination of nucleic acids Anal. Biochem. 1979, 94, 259-264 (Pubitemid 9173013)
38. Moore, P. L.; MacCoubrey, I. C.; Haugland, R. P. J. Cell Biol. 1990, 111, 58a (Abstract No. 304)
39. Hayes, J. D.; McLellan, L. Glutathione and glutathione-dependent enzymes represent a co-ordinately regulated defence against oxidative stress Free Radical Res. 1999, 31, 273-300 (Pubitemid 29452854)