Effects of alkyl side chain modification of coenzyme Q10 on mitochondrial respiratory chain function and cytoprotection

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 8, 2013, Pages 2346-2354

  Fash, David M ^a   Khdour, Omar M ^a   Sahdeo, Sunil J ^b   Goldschmidt, Ruth ^a   Jaruvangsanti, Jennifer ^a   Dey, Sriloy ^a   Arce, Pablo M ^a   Collin, Valérie C ^a   Cortopassi, Gino A ^b   Hecht, Sidney M ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Coenzyme Q10; Cytoprotection; Electron transport chain; Oxygen consumption; Reactive oxygen species

Indexed keywords

2 (10 CYCLOHEXYLDECYL) 5,6 DIMETHOXY 3 METHYLCYCLOHEXA 2,5 DIENE 1,4 DIONE; DECYLUBIQUINONE; GLUTATHIONE; IDEBENONE; MALEIC ACID DIETHYL ESTER; REACTIVE OXYGEN METABOLITE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; UBIDECARENONE; UBIDECARENONE DERIVATIVE; UBIQUINONE; UBIQUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CELL PROTECTION; CONTROLLED STUDY; DRUG DESIGN; ENZYME MODIFICATION; ENZYME SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA CELL; MAMMAL CELL; MITOCHONDRIAL MEMBRANE POTENTIAL; MITOCHONDRIAL RESPIRATION; NONHUMAN; OXYGEN CONSUMPTION; RESPIRATORY CHAIN;

ANIMALS; CATTLE; CELL LINE; CELL LINE, TUMOR; CYTOPROTECTION; ELECTRON TRANSPORT; HUMANS; LEUKEMIA; MEMBRANE POTENTIAL, MITOCHONDRIAL; MITOCHONDRIA; OXYGEN CONSUMPTION; REACTIVE OXYGEN SPECIES; RETINAL GANGLION CELLS; STRUCTURE-ACTIVITY RELATIONSHIP; UBIQUINONE;

MAMMALIA;

EID: 84875697384     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.01.075     Document Type: Article

References (42)

1. H.M. McBride, M. Neuspiel, and S. Wasiak Curr. Biol. 16 2006 R551
2. W.F. Graier, M. Frieden, and R. Malli Eur. J. Physiol. 455 2007 375
3. M. Bras, B. Queenan, and S.A. Susin Biochemistry (Moscow) 70 2005 231
4. M.P. Murphy Biochem. J. 417 2009 1
5. J.F. Turrens J. Physiol. 552 2003 335
6. B. Chance, H. Sies, and A. Boveris Physiol. Rev. 59 1979 527
7. I. Fridovich Ann. N.Y. Acad. Sci. 893 1999 13
8. J.M. Mátes, C. Pérez-Gómez, and I. Núñez de Castro Clin. Biochem. 32 1999 595
9. G.F. Gaetani, S. Galiano, L. Canepa, A.M. Ferraris, and H.N. Kirkman Blood 73 1989 334
10. J.S. Armstrong, O.M. Khdour, and S.M. Hecht FASEB J. 24 2010 2152
11. W.R. Markesbery, and J.M. Carney Brain Pathol. 9 1999 133
12. K.J. Barnham, C.L. Masters, and A.I. Bush Nat. Rev. Drug Disc. 3 2004 205
13. V. Calabrese, R. Lodi, C. Tonon, V. D'Agata, M. Sapienza, G. Scapagnini, A. Mangiameli, G. Pennisi, A.M. Stella, and D.A. Butterfield J. Neurol. Sci. 233 2005 145
14. M.T. Lin, and M.F. Beal Nature 443 2006 787
15. S. DiMauro, and E.A. Schon Annu. Rev. Neurosci. 31 2008 91
16. M. Bentinger, M. Tekle, and G. Dallner Biochem. Biophys. Res. Commun. 396 2010 74
17. F.L. Crane, Y. Hatefi, R.L. Lester, and C. Widmer Biochim. Biophys. Acta 25 1957 220
18. H. Lodish, A. Berk, S.L. Zipursky, P. Matsudaira, D. Baltimore, and J. Darnell Molecular Cell Biology 4th ed. 2000 W.H. Freeman New York p 675
19. A.M. James, R.A. Smith, and M.P. Murphy Arch. Biochem. Biophys. 423 2004 47
20. C.M. Quinzii, L.C. López, J. Von-Moltke, A. Naini, S. Krishna, M. Schuelke, L. Salviati, P. Navas, S. DiMauro, and M. Hirano FASEB J. 22 2008 1874
21. C.W. Shults, R.H. Haas, D. Passov, and M.F. Beal Ann. Neurol. 42 1997 261
22. M.E. Götz, A. Gerstner, R. Harth, A. Dirr, B. Janetzky, W. Kuhn, P. Riederer, and M. Gerlach J. Neural Transm. 107 2000 41
23. F. Rosenfeldt, D. Hilton, S. Pepe, and H. Krum BioFactors 18 2003 91
24. C.W. Shults, and R. Haas BioFactors 25 2005 117
25. H.N. Bhagavan, and R.K. Chopra Mitochondrion 7 2007 S78
26. M.P. Murphy Trends Biotechnol. 15 1997 326
27. R.A.J. Smith, C.M. Porteous, C.V. Coulter, and M.P. Murphy Eur. J. Biochem. 263 1999 709
28. G.F. Kelso, C.M. Porteous, C.V. Coulter, G. Hughes, W.K. Porteous, E.C. Ledgerwood, R.A.J. Smith, and M.P. Murphy J. Biol. Chem. 276 2001 4588
29. P.M. Arce, O.M. Khdour, R. Goldschmidt, J.S. Armstrong, and S.M. Hecht ACS Med. Chem. Lett. 2 2011 608
30. D.Y. Duveau, P.M. Arce, R.A. Schoenfeld, N. Raghav, G.A. Cortopassi, and S.M. Hecht Bioorg. Med. Chem. 18 2010 6429
31. L. Yu, F.D. Yang, and C.A. Yu J. Biol. Chem. 260 1985 963
32. Y.-P. Wan, R.H. Williams, K. Folkers, K.H. Leung, and E. Racker Biochem. Biophys. Res. Commun. 63 1975 11
33. M. Scholl, S. Ding, C.W. Lee, and R.H. Grubbs Org. Lett. 1 1999 953
34. M. Bérubé, and D. Poirer J. Enzyme Inhib. Med. Chem. 24 2009 832
35. L. Lu, and F. Chen Synth. Commun. 34 2004 4049
36. C.P. LeBel, H. Ischiropoulos, and S.C. Bondy Chem. Res. Toxicol. 5 1992 227
37. B. Ehrenberg, V. Montana, M.D. Wei, J.P. Wuskell, and L.M. Loew Biophys. J. 53 1988 785
38. A.L. Smith Methods Enzymol. 10 1967 81
39. A. Matsuno-Yagi, and Y. Hatefi J. Biol. Chem. 260 1985 11424
40. S.J. Leiris, O.M. Khdour, Z.J. Segerman, K.S. Tsosie, J.-C. Chapuis, and S.M. Hecht Bioorg. Med. Chem. 18 2010 3481
41. P.M. Arce, R. Goldschmidt, O.M. Khdour, M.M. Madathil, J. Jaruvangsanti, S. Dey, D.M. Fash, J.S. Armstrong, and S.M. Hecht Bioorg. Med. Chem. 20 2012 5188
42. O.M. Khdour, J. Lu, and S.M. Hecht Pharm. Res. 28 2011 2896