Mitochondria-targeted antioxidants

Mitochondrial Signaling in Health and Disease

Volumn , Issue , 2012, Pages 111-127

  Smith, Robin A J ^a   Hartley, Richard C ^b   Murphy, Michael P ^a  

^a UNIVERSITY OF OTAGO   (New Zealand)

^b UNIVERSITY OF GLASGOW   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85028106843     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (96)

1. Adlam, V. J., J. C. Harrison, C. M. Porteous, A. M. James, R. A. J. Smith, M. P. Murphy, and I. A. Sammut. 2005. Targeting an antioxidant to mitochondria decreases cardiac ischemia-reperfusion injury. FASEB J 19(9):1088-95.
2. Ames, B. N., M. K. Shigenaga, and T. M. Hagen. 1993. Oxidants, antioxidants, and the degenerative diseases of aging. Proc Natl Acad Sci USA 90:7915-22.
3. 2 emission and cellular redox state link excess fat intake to insulin resistance in both rodents and humans. J Clin Invest 119:573-81.
4. Appleby, R. D., W. K. Porteous, G. Hughes, A. M. James, D. Shannon, Y.-H. Wei, and M. P. Murphy. 1999. Quantitation and origin of the mitochondrial membrane potential in human cells lacking mitochondrial DNA. Eur J Biochem 262:108-16.
5. Asin-Cayuela, J., A. R. Manas, A. M. James, R. A. J. Smith, and M. P. Murphy. 2004. Fine-tuning the hydrophobicity of a mitochondria-targeted antioxidant. FEBS Lett 571(1-3):9-16.
6. Azzone, G. F., D. Pietrobon, and M. Zoratti. 1984. Determination of the proton electrochemical gradient across biological membranes. Curr Top Bioenerg 13:1-77.
7. Balaban, R. S., S. Nemoto, and T. Finkel. 2005. Mitochondria, oxidants, and aging. Cell 120(4):483-95.
8. Beckman, K. B., and B. N. Ames. 1998. The free radical theory of aging matures. Physiol Rev 78:547-81.
9. Bjelakovic, G., D. Nikolova, L. L. Gluud, R. G. Simonetti, and C. Gluud. 2008. Antioxidant supplements for prevention of mortality in healthy participants and patients with various diseases. Cochrane Database Syst Rev (2):CD007176.
10. Brand, M. D. 1995. Measurement of mitochondrial proton motive force. In Bioenergetics-A Practical Approach, edited by G. C. Brown and C. E. Cooper. Oxford: IRL.
11. Brown, S. E., M. F. Ross, A. Sanjuan-Pla, A. R. Manas, R. A. J. Smith, and M. P. Murphy. 2007. Targeting lipoic acid to mitochondria: synthesis and characterization of a triphenylphosphonium-conjugated alpha-lipoyl derivative. Free Radic Biol Med 42(12):1766-80.
12. Burns, R. J., and M. P. Murphy. 1997. Labeling of mitochondrial proteins in living cells by the thiol probe thiobutyltriphenylphosphonium bromide. Arch Biochem Biophys 339:33-9.
13. Burns, R. J., R. A. J. Smith, and M. P. Murphy. 1995. Synthesis and characterization of thiobutyltriphenylphosphonium bromide, a novel thiol reagent targeted to the mitochondrial matrix. Arch Biochem Biophys 322:60-8.
14. Chacko, B. K., C. Reily, A. Srivastava, M. S. Johnson, Y. Ye, E. Ulasova, A. Agarwal, K. R. Zinn, M. P. Murphy, B. Kalyanaraman, and V. Darley-Usmar. 2010. Prevention of diabetic nephropathy in Ins2(+/)(AkitaJ) mice by the mitochondria-targeted therapy MitoQ. Biochem J 432(1):9-19.
15. Chandran, K., D. Aggarwal, R. Q. Migrino, J. Joseph, D. McAllister, E. A. Konorev, W. E. Antholine, J. Zielonka, S. Srinivasan, N. G. Avadhani, and B. Kalyanaraman. 2009. Doxorubicin inactivates myocardial cytochrome c oxidase in rats: cardioprotection by Mito-Q. Biophys J 96(4):1388-98.
16. Chen, L. B. 1988. Mitochondrial membrane potential in living cells. Ann Rev Cell Biol 4:155-81.
17. Cocheme, H. M., and M. P. Murphy. 2010. Can antioxidants be effective therapeutics? Curr Opin Invest Drugs 11(4):426-31.
18. Davies, S. M., A. Poljak, M. W. Duncan, G. A. Smythe, and M. P. Murphy. 2001. Measurements of protein carbonyls, ortho- and meta-tyrosine and oxidative phosphorylation complex activity in mitochondria from young and old rats. Free Radic Biol Med 31(2):181-90.
19. Davis, S., M. J. Weiss, J. R. Wong, T. J. Lampidis, and L. B. Chen. 1985. Mitochondrial and plasma membrane potential cause unusual accumulation and retention of rhodamine 123 by human breast adenocarcinoma-derived MCF-7 cells. J Biol Chem 260:13844-50.
20. Dessolin, J., Schuler, M., Quinart, A., De Giorgi, F., Ghosez, L., and Ichas, F. 2002. Selective targeting of synthetic antioxidants to mitochondria: towards a mitochondrial medicine for neurodegenerative diseases? Eur J Pharmacol 447:155-61.
21. Dhanasekaran, A., S. Kotamraju, C. Karunakaran, S. V. Kalivendi, S. Thomas, J. Joseph, and B. Kalyanaraman. 2005. Mitochondria superoxide dismutase mimetic inhibits peroxideinduced oxidative damage and apoptosis: role of mitochondrial superoxide. Free Radic Biol Med 39(5):567-83.
22. Dikalova, A. E., A. T. Bikineyeva, K. Budzyn, R. R. Nazarewicz, L. McCann, W. Lewis, D. G. Harrison, and S. I. Dikalov. 2010. Therapeutic targeting of mitochondrial superoxide in hypertension. Circ Res 107(1):106-16.
23. Doughan, A. K., and S. I. Dikalov. 2007. Mitochondrial redox cycling of mitoquinone leads to superoxide production and cellular apoptosis. Antioxid Redox Signal 9(11):1825-36.
24. Duchen, M. R. 2004. Mitochondria in health and disease: Perspectives on a new mitochondrial biology. Mol Aspects Med 25(4):365-451.
25. Echtay, K. S., M. P. Murphy, R. A. J. Smith, D. A. Talbot, and M. D. Brand. 2002. Superoxide activates mitochondrial uncoupling protein 2 from the matrix side. Studies using targeted antioxidants. J Biol Chem 277(49):47129-35.
26. Esplugues, J. V., M. Rocha, C. Nunez, I. Bosca, S. Ibiza, J. R. Herance, A. Ortega, J. M. Serrador, P. D’Ocon, and V. M. Victor. 2006. Complex I dysfunction and tolerance to nitroglycerin: an approach based on mitochondrial-targeted antioxidants. Circ Res 99(10):1067-75.
27. Filipovska, A., G. F. Kelso, S. E. Brown, S. M. Beer, R. A. J. Smith, and M. P. Murphy. 2005. Synthesis and characterization of a triphenylphosphonium-conjugated peroxidase mimetic: insights into the interaction of ebselen with mitochondria. J Biol Chem 280(25): 24113-26.
28. Finkel, T. 2005. Opinion: radical medicine: treating ageing to cure disease. Nat Rev Mol Cell Biol 6(12):971-6.
29. Flewelling, R. F., and W. L. Hubbell. 1986. Hydrophobic ion interactions with membranes. Biophys J 49:531-40.
30. Gane, E. J., F. Weilert, D. W. Orr, G. F. Keogh, M. Gibson, M. M. Lockhart, C. M. Frampton, K. M. Taylor, R. A. J. Smith, and M. P. Murphy. 2010. The mitochondria-targeted antioxidant mitoquinone decreases liver damage in a phase II study of hepatitis C patients. Liver Int 30(7):1019-26.
31. Ghosh, A., K. Chandran, S. V. Kalivendi, J. Joseph, W. E. Antholine, C. J. Hillard, A. Kanthasamy, A. Kanthasamy, and B. Kalyanaraman. 2010. Neuroprotection by a mitochondria-targeted drug in a Parkinson’s disease model. Free Radic Biol Med 49(11):1674-84.
32. 10 improves endothelial function and attenuates cardiac hypertrophy. Hypertension 54:322-8.
33. Green, K., M. D. Brand, and M. P. Murphy. 2004. Prevention of mitochondrial oxidative damage as a therapeutic strategy in diabetes. Diabetes 53 (Suppl 1):S110-S118.
34. 2-reactive DEPMPO spin trap:a new and improved trap for the detection of superoxide. Chem Commun (Camb) (10):1083-5.
35. Horton, K. L., K. M. Stewart, S. B. Fonseca, Q. Guo, and S. O. Kelley. 2008. Mitochondriapenetrating peptides. Chem Biol 15(4):375-82.
36. Hu, Y., D. G. Rosen, Y. Zhou, L. Feng, G. Yang, J. Liu, and P. Huang. 2005. Mitochondrial manganese-superoxide dismutase expression in ovarian cancer: role in cell proliferation and response to oxidative stress. J Biol Chem 280(47):39485-92.
37. James, A. M., H. M. Cocheme, and M. P. Murphy. 2005. Mitochondria-targeted redox probes as tools in the study of oxidative damage and ageing. Mech Ageing Dev 126(9):982-6.
38. James, A. M., H. M. Cocheme, R. A. J. Smith, and M. P. Murphy. 2005. Interactions of mitochondria-targeted and untargeted ubiquinones with the mitochondrial respiratory chain and reactive oxygen species. Implications for the use of exogenous ubiquinones as therapies and experimental tools. J Biol Chem 280(22):21295-312.
39. James, A. M., M. S. Sharpley, A. R. Manas, F. E. Frerman, J. Hirst, R. A. J. Smith, and M. P. Murphy. 2007. Interaction of the mitochondria-targeted antioxidant MitoQ with phospholipid bilayers and ubiquinone oxidoreductases. J Biol Chem 282(20):14708-18.
40. James, A. M., R. A. J. Smith, and M. P. Murphy. 2004. Antioxidant and prooxidant properties of mitochondrial coenzyme Q. Arch Biochem Biophys 423(1):47-56.
41. Jauslin, M. L., T. Meier, R. A. J. J. Smith, and M. P. Murphy. 2003. Mitochondria-targeted antioxidants protect Friedreich ataxia fibroblasts from endogenous oxidative stress more effectively than untargeted antioxidants. FASEB J 17:1972-4.
42. Kelso, G. F., C. M. Porteous, C. V. Coulter, G. Hughes, W. K. Porteous, E. C. Ledgerwood, R. A. J. J. Smith, and M. P. Murphy. 2001. Selective targeting of a redox-active ubiquinone to mitochondria within cells. J Biol Chem 276:4588-96.
43. Ketterer, B., B. Neumcke, and P. Laeuger. 1971. Transport mechanism of hydrophobic ions across through lipid bilayers. J Membr Biol 5:225-45.
44. Kroemer, G., N. Zamzami, and S. A. Susin. 1997. Mitochondrial control of apoptosis. Immunol Today 18:44-51.
45. Larrea, E., O. Beloqui, M. A. Munoz-Navas, M. P. Civeira, and J. Prieto. 1998. Superoxide dismutase in patients with chronic hepatitis C virus infection. Free Radic Biol Med 24(7-8):1235-41.
46. Lemasters, J. J., A.-L. Nieminen, T. Qian, L. C. Trost, S. P. Elmore, Y. Nishimura, R. A. Crowe, W. E. Cascio, C. A. Bradham, D. A. Brenner, and B. Herman. 1998. The mitochondrial permeability transition in cell death: a common mechanism in necrosis, apoptosis and autophagy. Biochim Biophys Acta 1366:177-96.
47. Levine, R. L., J. A. Williams, E. R. Stadtman, and E. Shacter. 1994. Carbonyl assays for determination of oxidatively damaged proteins. Meth Enzymol 233:346-357.
48. Li, Y., H. Zhang, J. P. Fawcett, and I. G. Tucker. 2007. Quantitation and metabolism of mitoquinone, a mitochondria-targeted antioxidant, in rat by liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom 21(13):1958-64.
49. 10), a mitochondria-targeted antioxidant, in rat. Asian J Pharm Sci 5:106-13.
50. Liberman, E. A., and V. P. Skulachev. 1970. Conversion of biomembrane-produced energy into electric form. IV. General discussion. Biochim Biophys Acta 216(1):30-42.
51. Liberman, E. A., V. P. Topali, L. M. Tsofina, A. A. Jasaitis, and V. P. Skulachev. 1969. Mechanism of coupling of oxidative phosphorylation and the membrane potential of mitochondria. Nature 222:1076-8.
52. Lowes, D. A., B. M. Thottakam, N. R. Webster, M. P. Murphy, and H. F. Galley. 2008. The mitochondria-targeted antioxidant MitoQ protects against organ damage in a lipopolysaccharide- peptidoglycan model of sepsis. Free Radic Biol Med 45(11):1559-65.
53. Mahon, K. P., T. B. Potocky, D. Blair, M. D. Roy, K. M. Stewart, T. C. Chiles, and S. O. Kelley. 2007. Deconvolution of the cellular oxidative stress response with organelle-specific peptide conjugates. Chem Biol 14(8):923-30.
54. Miller, E. W., O. Tulyathan, E. Y. Isacoff, and C. J. Chang. 2007. Molecular imaging of hydrogen peroxide produced for cell signaling. Nat Chem Biol 3(5):263-7.
55. Mitchell, T., D. Rotaru, H. Saba, R. A. J. Smith, M. P. Murphy, and L. MacMillan-Crow. 2011. The mitochondria-targeted antioxidant Mitoquinone protects against cold storage injury of renal tubular cells and rat kidneys J Pharm Exp Ther 336(3):682-92.
56. Murphy, M. P. 1997. Targeting bioactive compounds to mitochondria. Trends Biotech 15:326-30.
57. Murphy, M. P. 2009a. How mitochondria produce reactive oxygen species. Biochem J 417(1):1-13.
58. Murphy, M. P. 2009b. Mitochondria-a neglected drug target. Curr Opin Invest Drugs 10(10):1022-4.
59. Murphy, M. P., K. S. Echtay, F. H. Blaikie, J. Asin-Cayuela, H. M. Cocheme, K. Green, J. A. Buckingham, E. R. Taylor, F. Hurrell, G. Hughes, S. Miwa, C. E. Cooper, D. A. Svistunenko, R. A. J. Smith, and M. D. Brand. 2003. Superoxide activates uncoupling proteins by generating carbon-centered radicals and initiating lipid peroxidation: studies using a mitochondria-targeted spin trap derived from alpha-phenyl-N -tert -butylnitrone. J Biol Chem 278(49):48534-45.
60. Murphy, M. P., and R. A. J. Smith. 2000. Drug delivery to mitochondria: the key to mitochondrial medicine. Adv Drug Deliv Rev 41:235-50.
61. Murphy, M. P., and R. A. J. Smith. 2007. Targeting antioxidants to mitochondria by conjugation to lipophilic cations. Annu Rev Pharmacol Toxicol 47:629-56.
62. Neuzil, J., C. Widen, N. Gellert, E. Swettenham, R. Zobalova, L. F. Dong, X. F. Wang, C. Lidebjer, H. Dalen, J. P. Headrick, and P. K. Witting. 2007. Mitochondria transmit apoptosis signalling in cardiomyocyte-like cells and isolated hearts exposed to experimental ischemia-reperfusion injury. Redox Rep 12(3):148-62.
63. Nicholls, D. G., and S. J. Ferguson. 2002. Bioenergetics 3. London: Academic Press.
64. O’Malley, Y., B. D. Fink, N. C. Ross, T. E. Prisinzano, and W. I. Sivitz. 2006. Reactive oxygen and targeted antioxidant administration in endothelial cell mitochondria. J Biol Chem 281(52):39766-75.
65. 2+ in mitochondrial dysfunction and disease. Cell Calcium 45(6):643-50.
66. Porteous, C. M., A. Logan, C. Evans, E. C. Ledgerwood, D. K. Menon, F. Aigbirhio, R. A. J. Smith, and M. P. Murphy. 2010. Rapid uptake of lipophilic triphenylphosphonium cations by mitochondria in vivo following intravenous injection: implications for mitochondria-specific therapies and probes. Biochim Biophys Acta 1800(9):1009-17.
67. Ripcke, J., K. Zarse, M. Ristow, and M. Birringer. 2009. Small-molecule targeting of the mitochondrial compartment with an endogenously cleaved reversible tag. Chem Bio Chem 10:1689-96.
68. Robinson, K. M., M. S. Janes, M. Pehar, J. S. Monette, M. F. Ross, T. M. Hagen, M. P. Murphy, and J. S. Beckman. 2006. Selective fluorescent imaging of superoxide in vivo using ethidium-based probes. Proc Natl Acad Sci USA 103(41):15038-43.
69. Rodriguez-Cuenca, S., H. M. Cocheme, A. Logan, I. Abakumova, T. A. Prime, C. Rose, A. Vidal-Puig, A. C. Smith, D. C. Rubinsztein, I. M. Fearnley, B. A. Jones, S. Pope, S. J. Heales, B. Y. Lam, S. G. Neogi, I. McFarlane, A. M. James, R. A. J. Smith, and M. P. Murphy. 2010. Consequences of long-term oral administration of the mitochondria-targeted antioxidant MitoQ to wild-type mice. Free Radic Biol Med 48(1):161-72.
70. Ross, M. F., G. F. Kelso, F. H. Blaikie, A. M. James, H. M. Cocheme, A. Filipovska, T. Da Ros, T. R. Hurd, R. A. Smith, and M. P. Murphy. 2005. Lipophilic triphenylphosphonium cations as tools in mitochondrial bioenergetics and free radical biology. Biochemistry (Mosc) 70(2):222-30.
71. Ross, M. F., T. A. Prime, I. Abakumova, A. M. James, C. M. Porteous, R. A. J. Smith, and M. P. Murphy. 2008. Rapid and extensive uptake and activation of hydrophobic triphenylphosphonium cations within cells. Biochem J 411:633-45.
72. Santos, J. H., J. N. Meyer, B. S. Mandavilli, and B. Van Houten. 2006. Quantitative PCRbased measurement of nuclear and mitochondrial DNA damage and repair in mammalian cells. Meth Mol Biol 314:183-99.
73. Saraste, M. 1999. Oxidative phosphorylation at the fin de siecle. Science 283:1488-93.
74. Skulachev, V. P., V. N. Anisimov, Y. N. Antonenko, L. E. Bakeeva, B. V. Chernyak, V. P. Erichev, O. F. Filenko, N. I. Kalinina, V. I. Kapelko, N. G. Kolosova, B. P. Kopnin, G. A. Korshunova, M. R. Lichinitser, L. A. Obukhova, E. G. Pasyukova, O. I. Pisarenko, V. A. Roginsky, E. K. Ruuge, Senin II, Severina II, M. V. Skulachev, I. M. Spivak, V. N. Tashlitsky, V. A. Tkachuk, M. Y. Vyssokikh, L. S. Yaguzhinsky, and D. B. Zorov. 2009. An attempt to prevent senescence:a mitochondrial approach. Biochim Biophys Acta 1787(5):437-61.
75. Smith, R. A. J., G. F. Kelso, A. M. James, and M. P. Murphy. 2004. Targeting coenzyme Q derivatives to mitochondria. Methods Enzymol 382:45-67.
76. Smith, R. A. J., and M. P. Murphy. 2010. Animal and human studies with the mitochondriatargeted antioxidant MitoQ. Ann N Y Acad Sci 1201:96-103.
77. Smith, R. A. J., C. M. Porteous, C. V. Coulter, and M. P. Murphy. 1999. Targeting an antioxidant to mitochondria. Eur J Biochem 263:709-16.
78. Smith, R. A. J., C. M. Porteous, A. M. Gane, and M. P. Murphy. 2003. Delivery of bioactive molecules to mitochondria in vivo. Proc Natl Acad Sci USA 100:5407-12.
79. Snow, B. J., F. L. Rolfe, M. M. Lockhart, C. M. Frampton, J. D. O’Sullivan, V. Fung, R. A. J.Smith, M. P. Murphy, and K. M. Taylor. 2010. A double-blind, placebo-controlled study to assess the mitochondria-targeted antioxidant MitoQ as a disease-modifying therapy in Parkinson’s disease. Mov Disord 25(11):1670-4.
80. Supinski, G. S., M. P. Murphy, and L. A. Callahan. 2009. MitoQ administration prevents endotoxin-induced cardiac dysfunction. Am J Physiol Regul Integr Comp Physiol 297(4):R1095-R1102.
81. Szeto, H. H. 2006a. Cell-permeable, mitochondrial-targeted, peptide antioxidants. AAPS J 8(2):E277-E283.
82. Szeto, H. H. 2006b. Mitochondria-targeted peptide antioxidants: novel neuroprotective agents. AAPS J 8(3):E521-E531.
83. Szeto, H. H. 2008. Mitochondria-targeted cytoprotective peptides for ischemia-reperfusion injury. Antiox Redox Signal 10(3):601-19.
84. Szeto, H. H., J. L. Lovelace, G. Fridland, Y. Soong, J. Fasolo, D. Wu, D. M. Desiderio, and P. W. Schiller. 2001. In vivo pharmacokinetics of selective mu-opioid peptide agonists. J Pharm Exp Ther 298(1):57-61.
85. Szeto, H. H., P. W. Schiller, K. Zhao, and G. Luo. 2005. Fluorescent dyes alter intracellular targeting and function of cell-penetrating tetrapeptides. FASEB J 19(1):118-20.
86. Szewczyk, A., and L. Wojtczak. 2002. Mitochondria as a pharmacological target. Pharmacol Rev 54(1):101-27.
87. Teicher, B. A., and S. A. Holden. 1987. Antitumor and radiosensitizing activity of several platinum-(+) dye complexes. Radiat Res 109(1):58-67.
88. Teicher, B. A., S. A. Holden, and K. N. Cathcart. 1987. Efficacy of Pt(Rh-123)2 as a radiosensitizer with fractionated X rays. Int J Radiat Oncol Biol Phys 13(8):1217-24.
89. Trnka, J., F. H. Blaikie, R. A. J. Smith, and M. P. Murphy. 2008. A mitochondria-targeted nitroxide is reduced to its hydroxylamine by ubiquinol in mitochondria. Free Radic Biol Med 44:1406-19.
90. Vergeade, A., P. Mulder, C. Vendeville-Dehaudt, F. Estour, D. Fortin, R. Ventura-Clapier, C. Thuillez, and C. Monteil. 2010. Mitochondrial impairment contributes to cocaineinduced cardiac dysfunction: Prevention by the targeted antioxidant MitoQ. Free Radic Biol Med 49(5):748-56.
91. Wallace, D. C. 1999. Mitochondrial diseases in man and mouse. Science 283:1482-8.
92. Yang, L., K. Zhao, N. Y. Calingasan, G. Luo, H. H. Szeto, and M. F. Beal. 2009. Mitochondria targeted peptides protect against 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine neurotoxicity. Antioxid Redox Signal 11(9):2095-104.
93. Yousif, L. F., K. M. Stewart, K. L. Horton, and S. O. Kelley. 2009. Mitochondria-penetrating peptides: Sequence effects and model cargo transport. Chem Bio Chem 10(12):2081-8.
94. Yousif, L. F., K. M. Stewart, and S. O. Kelley. 2009. Targeting mitochondria with organellespecific compounds: Strategies and applications. Chem Bio Chem 10(12):1939-50.
95. + net charge opioid tetrapeptide. J Pharm Exp Ther 304(1):425-32.
96. Zhao, K., G. M. Zhao, D. Wu, Y. Soong, A. V. Birk, P. W. Schiller, and H. H. Szeto. 2004. Cell-permeable peptide antioxidants targeted to inner mitochondrial membrane inhibit mitochondrial swelling, oxidative cell death, and reperfusion injury. J Biol Chem 279(33):34682-90.