Fine-tuning the hydrophobicity of a mitochondria-targeted antioxidant

FEBS Letters

Volumn 571, Issue 1-3, 2004, Pages 9-16

  Asin Cayuela, Jordi ^a   Manas, Abdul Rahman B ^b   James, Andrew M ^a   Smith, Robin A J ^b   Murphy, Michael P ^a  

^a WELLCOME TRUST SANGER INSTITUTE   (United Kingdom)

^b UNIVERSITY OF OTAGO   (New Zealand)

Author keywords

Antioxidant; CoQ 0, 2,3 dimethoxy 5 methyl 1,4 benzoquinone; FCCP, carbonylcyanide p trifluoromethoxyphenylhydrazone; Lipophilic cation; MDA, malondialdehyde; Mitochondria; MitoQ; Oxidative damage

Indexed keywords

ANTIOXIDANT; CARBON; CARBON 11; PHOSPHATE;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CELL MEMBRANE POTENTIAL; CONTROLLED STUDY; DRUG EFFICACY; DRUG SYNTHESIS; HYDROPHOBICITY; LIVER MITOCHONDRION; MEMBRANE BINDING; MITOCHONDRION; NONHUMAN; OXIDATIVE STRESS; PHOSPHOLIPID BILAYER; PRIORITY JOURNAL; RAT;

ANTIOXIDANTS; BIOLOGICAL TRANSPORT; CARBONYL CYANIDE P-TRIFLUOROMETHOXYPHENYLHYDRAZONE; INTRACELLULAR MEMBRANES; KINETICS; MITOCHONDRIA; MODELS, BIOLOGICAL; ORGANOPHOSPHORUS COMPOUNDS; UBIQUINONE;

EID: 3342989837     PISSN: 00145793     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.febslet.2004.06.045     Document Type: Article

References (40)

1. Wallace D.C. Science. 283:1999;1482-1488
2. Wallace D.C. Proc. Natl. Acad. Sci. USA. 91:1994;8739-8746
3. Beckman K.B., Ames B.N. Physiol. Rev. 78:1998;547-581
4. Raha S., Robinson B.H. Trends Biochem. Sci. 25:2000;502-508
5. Skulachev V.P. Quart. Rev. Biophys. 29:1996;169-202
6. Finkel T., Holbrook N.J. Nature. 408:2000;239-247
7. Finkel T. Curr. Opin. Cell Biol. 10:1998;248-253
8. Smith R.A., Kelso G.F., James A.M., Murphy M.P. Meth. Enzymol. 382:2004;45-67
9. Murphy M.P. Exp. Opin. Biol. Ther. 1:2001;753-764
10. Murphy M.P. Trends Biotechnol. 15:1997;326-330
11. Murphy M.P., Smith R.A.J. Adv. Drug Deliv. Rev. 41:2000;235-250
12. Liberman E.A., Topali V.P., Tsofina L.M., Jasaitis A.A., Skulachev V.P. Nature. 222:1969;1076-1078
13. Kelso G.F., Porteous C.M., Coulter C.V., Hughes G., Porteous W.K., Ledgerwood E.C., Smith R.A.J., Murphy M.P. J. Biol. Chem. 276:2001;4588-4596
14. Jauslin M.L., Meier T., Smith R.A.J., Murphy M.P. FASEB J. 17:2003;1972-1974
15. Saretzki G., Murphy M.P., von Zglinicki T. Aging Cell. 2:2003;141-143
16. Smith R.A.J., Porteous C.M., Gane A.M., Murphy M.P. Proc. Natl. Acad. Sci. USA. 100:2003;5407-5412
17. Hwang P.M., Bunz F., Yu J., Rago C., Chan T.A., Murphy M.P., Kelso G.F., Smith R.A.J., Kinzler K.W., Vogelstein B. Nature Med. 7:2001;1111-1117
18. Echtay K.S., Roussel D., St-Pierre J., Jekabsons M.B., Cadenas S., Stuart J.A., Harper J.A., Roebuck S.J., Morrison A., Pickering S., Clapham J.C., Brand M.D. Nature. 415:2002;96-99
19. Murphy M.P., Echtay K.S., Blaikie F.H., Asin-Cayuela J., Cocheme H.M., Green K., Buckingham J.A., Taylor E.R., Hurrell F., Hughes G., Miwa S., Cooper C.E., Svistunenko D.A., Smith R.A., Brand M.D. J. Biol. Chem. 278:2003;48534-48545
20. Ketterer B., Neumcke B., Laeuger P. J. Membr. Biol. 5:1971;225-245
21. Cafiso D.S., Hubbell W.L. Annu. Rev. Biophys. Bioeng. 10:1981;217-244
22. Flewelling R.F., Hubbell W.L. Biophys. J. 49:1986;531-540
23. Ono A., Miyauchi S., Demura M., Asakura T., Kamo N. Biochemistry. 33:1994;4312-4318
24. Carpino L.A., Triolo S.A., Berglund R.A. J. Org. Chem. 54:1989;3303-3310
25. Lipshutz B.H., Kim S.-K., Mollard P., Stevens K.L. Tetrahedron. 54:1998;1241-1253
26. Yoshioka, T., Nishi, T., Kanai, T., Aizawa, Y., Wada, K., Fujita, T., and Horikoshi, H. (1993), Eur. Pat. Appl. EP 549366 A1 19930630
27. Yu C.A., Yu L. Biochemistry. 21:1982;4096-4101
28. Smith R.A.J., Porteous C.M., Coulter C.V., Murphy M.P. Eur. J. Biochem. 263:1999;709-716
29. Chappell J.B., Hansford R.G. Birnie G.D. Subcellular Components: Preparation and Fractionation. 1972;77-91 Butterworths, London
30. Gornall A.G., Bardawill C.J., David M.M. J. Biol. Chem. 177:1949;751-766
31. Brand M.D. Brown G.C., Cooper C.E. Bioenergetics - A Practical Approach. 1995;39-62 IRL, Oxford
32. Brown G.C., Brand M.D. Biochem. J. 225:1985;399-405
33. Davey G.P., Tipton K.F., Murphy M.P. Biochem. J. 288:1992;439-443
34. Kamo N., Muratsugu M., Hongoh R., Kobatake Y. J. Membr. Biol. 49:1979;105-121
35. Tanoue Y., Terada A., Taniguchi H., Okuma T., Kaai H., Anan M., Kakara Y., Doi M., Morishita S. Bull. Chem. Soc. Japan. 66:1993;3712-3715
36. Rathore R., Bosch E., Kochi J.K. Tetrahedron Letts. 35:1994;1335-1338
37. Bosch E., Rathore R., Kochi J.K. J. Org. Chem. 59:1994;2529-2536
38. Liu B., Gu L., Zhang J. Recueil des Travaux Chimiques des Pays-Bas. 110:1991;104-110
39. James A.M., Smith R.A., Murphy M.P. Arch. Biochem. Biophys. 423:2004;47-56
40. Ernster L., Forsmark P., Nordenbrand K. Biofactors. 3:1992;241-248