Kinetic Analysis of Permeation of Mitochondria-Targeted Antioxidants Across Bilayer Lipid Membranes

Andersen OS, Fuchs M (1975) Potential energy barriers to ion transport within lipid bilayers. Studies with tetraphenylborate. Biophys J 15:795–830 Antonenko YN, Avetisyan AV, Bakeeva LE, Chernyak BV, Chertkov VA, Domnina LV, Ivanova OYu, Izyumov DS, Khailova LS, Klishin SS, Korshunov SS, Korshunova GA, Kovaleva NA, Lyamzaev KG, Muntyan MS, Nepryakhina OK, Pashkovskaya AA, Pletjushkina OYu, Pustovidko AV, Rokitskaya TI, Ruuge EK, Saprunova VB, Severina II, Simonyan RA, Skulachev IV, Skulachev MV, Sumbatyan NV, Sviryaeva IV, Tashlitsky VN, Tikhomirova NK, Vassiliev YM, Vyssokikh MYu, Yaguzhinsky LS, Skulachev VP (2008a) Mitochondria-targeted derivative of plastoquinone as a tool to interrupt execution of an aging program. Biochemistry (Mosc) (in press) Antonenko YN, Roginsky VA, Pashkovskaya AA, Rokitskaya TI, Kotova EA, Zaspa AA, Chernyak BV, Skulachev VP (2008b) Protective effects of mitochondria-targeted antioxidant SkQ in aqueous and lipid membrane environments. J Membr Biol 222:141–149 Bakeeva LE, Grinius LL, Jasaitis AA, Kuliene VV, Levitsky DO, Liberman EA, Severina II, Skulachev VP (1970) Conversion of biomembrane-produced energy into electric form. II. Intact mitochondria. Biochim Biophys Acta 216:13–21 Benz R (1988) Structural requirement for the rapid movement of charged molecules across membranes. Experiments with tetraphenylborate analogues. Biophys J 54:25–33 Brock W, Stark G, Jordan PC (1981) A laser-temperature-jump method for the study of the rate of transfer of hydrophobic ions and carriers across the interface of thin lipid membranes. Biophys Chem 13:329–348 Cafiso DS, Hubbell WL (1982) Transmembrane electrical currents of spin-labeled hydrophobic ions. Biophys J 39:263–272 Flewelling RF, Hubbell WL (1986a) Hydrophobic ion interactions with membranes thermodynamic analysis of tetraphenylphosphonium binding to vesicles. Biophys J 49:531–540 Flewelling RF, Hubbell WL (1986b) The membrane dipole potential in a total potential model. applications to hydrophobic ion interactions with membranes. Biophys J 49:541–552 Fujii T, Tamura A, Yamane T (1985) Trans-bilayer movement of added phosphatidylcholine and lysophosphatidylcholine species with various acyl chain lengths in plasma membrane of intact human erythrocytes. J Biochem 98:1221–1227 Grinius LL, Jasaitis AA, Kadziauskas YP, Liberman EA, Skulachev VP, Topali VP, Tsofina LM, Vladimirova MA (1970) Conversion of biomembrane-produced energy into electric form. I. Submitochondrial particles. Biochim Biophys Acta 216:1–12 Homan R, Pownall HJ (1988) Transbilayer diffusion of phospholipids: dependence on headgroup structure and acyl chain length. Biochim Biophys Acta 938:155–166 James AM, Cocheme HM, Smith RA, Murphy MP (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 280:21295–21312 James AM, Sharpley MS, Manas AR, Frerman FE, Hirst J, Smith RA, Murphy MP (2007) Interaction of the mitochondria-targeted antioxidant MitoQ with phospholipid bilayers and ubiquinone oxidoreductases. J Biol Chem 282:14708–14718 Jauslin ML, Meier T, Smith RA, Murphy MP (2003) Mitochondria-targeted antioxidants protect Friedreich ataxia fibroblasts from endogenous oxidative stress more effectively than untargeted antioxidants. FASEB J 17:1972–1974 Jemiota-Rzeminska M, Latowski D, Strzalka K (2001) Incorporation of plastoquinone and ubiquinone into liposome membranes studied by HPLC analysis The effect of side chain length and redox state of quinone. Chem Phys Lipids 110:85–94 Junges R, Kolb HA (1983) Noise analysis and relaxation experiments of transport of hydrophobic anions across lipid membranes at equilibrium and nonequilibrium. Biophys Chem 17:301–312 Kelso GF, Porteous CM, Coulter CV, Hughes G, Porteous WK, Ledgerwood EC, Smith RA, Murphy MP (2001) Selective targeting of a redox-active ubiquinone to mitochondria within cells: antioxidant and antiapoptotic properties. J Biol Chem 276:4588–4596 Kelso GF, Porteous CM, Hughes G, Ledgerwood EC, Gane AM, Smith RA, Murphy MP (2002) Prevention of mitochondrial oxidative damage using targeted antioxidants. Ann N Y Acad Sci 959:263–274 Ketterer B, Neumcke B, Läuger P (1971) Transport mechanism of hydrophobic ions through lipid bilayer membranes. J Membr Biol 5:225–245 LeBlanc OH (1969) Tetraphenylborate conductance through lipid bilayer membranes. Biochim Biophys Acta 193:350–360 Liberman EA, Skulachev VP (1970) Conversion of biomembrane-produced energy into electric form IV. General discussion. Biochim Biophys Acta 216:30–42 Liberman EA, Topaly VP (1969) Permeability of biomolecular phospholipid membranes for fat-soluble ions. Biofizika 14:452–461 Liberman EA, Topaly VP, Tsofina LM, Jasaitis AA, Skulachev VP (1969) Mechanism of coupling of oxidative phosphorylation and the membrane potential of mitochondria. Nature 222:1076–1078 Mclaughlin S (1977) Electrostatic potentials at membrane solution interfaces. Curr Top Membr Transport 9:71–144 Melikyan GB, Deriy BN, Ok DC, Cohen FS (1996) Voltage-dependent translocation of R18 and DiI across lipid bilayers leads to fluorescence changes. Biophys J 71:2680–2691 Mueller P, Rudin DO, Tien HT, Wescott WC (1963) Methods for the formation of single bimolecular lipid membranes in aqueous solution. J Phys Chem 67:534–535 Murphy MP, Smith RA (2007) Targeting antioxidants to mitochondria by conjugation to lipophilic cations. Annu Rev Pharmacol Toxicol 47:629–656 Orbach E, Finkelstein A (1980) The nonelectrolyte permeability of planar lipid bilayer membranes. J Gen Physiol 75:427–436 Pickar AD, Benz R (1978) Transport of oppositely charged lipophilic probe ions in lipid bilayer membranes having various structures. J Membr Biol 44:353–376 Rich PR, Harper R (1990) Partition coefficients of quinones and hydroquinones and their relation to biochemical reactivity. FEBS Lett 269:139–144 Rottenberg H (1984) Membrane potential and surface potential in mitochondria: uptake and binding of lipophilic cations. J Membr Biol 81:127–138 Saretzki G, Murphy MP, von Zglinicki T (2003) MitoQ counteracts telomere shortening and elongates lifespan of fibroblasts under mild oxidative stress. Aging Cell 2:141–143 Sedgwick EG, Bragg PD (1993) Mechanism of uptake of the fluorescent dye 2-(4-dimethylaminostyryl)-1-ethylpyridinium cation (DMP+) by phospholipid vesicles. Biochim Biophys Acta 1146:113–120 Severin SE, Skulachev VP, Yaguzhinskii LS (1970) Possible role of carnitine in the transport of fatty acids through the mitochondrial membrane [in Russian]. Biokhimiia 35:1250–1253 Severina II, Vyssokikh MY, Pustovidko AV, Simonyan RA, Rokitskaya TI, Skulachev VP (2007) Effects of lipophilic dications on planar bilayer phospholipid membrane and mitochondria. Biochim Biophys Acta 1767:1164–1168 Skulachev VP (2007) A biochemical approach to the problem of aging: “megaproject” on membrane-penetrating ions. The first results and prospects. Biochemistry (Mosc) 72:1385–1396 Smith RA, Porteous CM, Coulter CV, Murphy MP (1999) Selective targeting of an antioxidant to mitochondria. Eur J Biochem 263:709–716 Sokolov VS, Mirsky VM (2004) Electrostatic potentials of bilayer lipid membranes: basic research and analytical applications. In: Thin layer electrochemical sensors and biosensors: technology and performance. pp 255–291 Walter A, Gutknecht J (1986) Permeability of small nonelectrolytes through lipid bilayer membranes. J Membr Biol 90:207–217 Xiang TX, Anderson BD (1994) The relationship between permeant size and permeability in lipid bilayer membranes. J Membr Biol 140:111–122 Zimmermann D, Kiesel M, Terpitz U, Zhou A, Reuss R, Kraus J, Schenk WA, Bamberg E, Sukhorukov VL (2008) A combined patch-clamp and electrorotation study of the voltage- and frequency-dependent membrane capacitance caused by structurally dissimilar lipophilic anions. J Membr Biol 221:107–121