Role of membrane charge and semiquinone structure on naphthosemiquinone derivatives and 1,4-benzosemiquinone disproportionation and membrane-buffer distribution coefficients

References

• Ludewig M. Toxic quinones produced by mammalian defense cells—causative agents for autoimmune reactions?. Medical Hypotheses 1993; 41: 375–377
   PubMedGoogle Scholar
• Sebban P., Maroti P., Hanson D.K. Electron and proton transfer to the quinones in bacterial photosynthetic reaction centers: insight from combined approaches of molecular genetics and biophysics. Biochimie 1995; 77: 677–694
   PubMedGoogle Scholar
• Ross D., Beall H., Traver R.D., Siegel D., Phillips R.M., Gibson N.W. Bioactivation of quinones by DT-diaphorase, molecular, biochemical, and chemical studies. Oncology Research 1994; 6: 493–500
   PubMed Web of Science ®Google Scholar
• Workman P. Bioreductive mechanisms. International Journal of Radiation Oncology, Biology, Physics 1992; 22: 631–637
   PubMed Web of Science ®Google Scholar
• Dix T.A., Aikens J. Mechanisms and biological relevance of lipid peroxidation initiation. Chemical Research in Toxicology 1993; 6: 2–18
   PubMed Web of Science ®Google Scholar
• Haber F., Weiss J. The catalytic decomposition of hydrogen peroxide by iron salts. Proceedings of the Royal Society of London (A) 1934; 147: 332–342
   Google Scholar
• Smotkin E.S., Moy F.T., Plachy W.Z. Dioxygen solubility in aqueous phosphatidylcholine dispersions. Biochimica et Biophysica Acta 1991; 1061: 33–38
   PubMedGoogle Scholar
• Roginsky V.A., Barsukova T.K., Bruchelt G., Stegmann H.B. Kinetics of redox interaction between substituted 1,4-benzoquinones and ascorbate under aerobic conditions: critical phenomena. Free Radical Research 1998; 29: 115–125
   PubMed Web of Science ®Google Scholar
• Graham D.G., Tiffany S.M., Bell W.R., Gutknecht W.F. Autoxidation versus covalent binding of quinones as the mechanism of toxicity of dopamine, 6-hydroxydopamine, and related compounds toward C1300 neuroblastoma cells in vitro. Molecular Pharmacology 1978; 14: 644–653
   PubMed Web of Science ®Google Scholar
• Eyer P. Effects of superoxide dismutase on the autoxidation of 1,4-hydroquinone. Chemico-Biological Interactions 1991; 80: 159–176
   PubMed Web of Science ®Google Scholar
• Zhang L., Bandy B., Davison A.J. Effects of metals, ligands and antioxidants on the reaction of oxygen with 1,2,4-benzenetriol. Free Radical Biology and Medicine 1996; 20: 495–505
   PubMed Web of Science ®Google Scholar
• Roginsky V., Barsukova T. Kinetics of oxidation of hydroquinones by molecular oxygen. Effect of superoxide dismutase. Journal of the Chemical Society, Perkin Transactions 2 2000; 1575–1582
   Google Scholar
• Roginsky V.A., Barsukva T.K., Bruchelt G., Stegmann H. The oxidation of catecholamines and 6-hydroxy-dopamine by molecular oxygen: effect of ascorbate. Zeitschrift fur Naturforschung C 1997; 52: 380–390
   Google Scholar
• Munday R. Autoxidation of naphthohydroquinones: effects of metals, chelating agents, and superoxide dismutase. Free Radical Biology and Medicine 1997; 22: 689–695
   PubMed Web of Science ®Google Scholar
• Alegría A.E., Rodriguez M.S., Hernandez J. Semiquinones derived from anthraquinone-containing antitumor drugs can partition into lecithin bilayers. Biochimica et Biophysica Acta 1990; 1035: 51–55
   PubMedGoogle Scholar
• Alegría A.E., Santiago G. Adriamycin and daunomycin semiquinones membrane/buffer partition constants using the spin-broadening technique. Archives of Biochemistry and Biophysics 1997; 346: 91–95
   PubMedGoogle Scholar
• Alegría A.E., Rivera S., Hernandez M., Ufret R., Morales M. Membrane-buffer partition coefficients of semiquinones using the spin-broadening technique. Journal of the Chemical Society, Faraday Transactions 1993; 89: 3773–3777
   Google Scholar
• Arcamone F., Cassinelli G. Biosynthetic anthracyclines. Current Medicinal Chemistry 1998; 5: 391–419
   PubMed Web of Science ®Google Scholar
• Aikawa M., Kamanura K., Shiraishi S., Matsumoto Y., Arwati H., Torii M., Ito Y., Takeuchi T., Tandler B. Membrane knobs of unfixed Plasmodium falciparum infected erythrocytes: new findings as revealed by atomic force microscopy and surface potential spectroscopy. Experimental Parasitology 1996; 84: 339–343
   PubMed Web of Science ®Google Scholar
• Ahmed K., Nakagawa T., Nakano Y., Martinez G., Ichinose A., Zheng C.H., Akaki M., Aikawa M., Nagatake T. Attachment of Moraxella catarrhalis occurs to the positively charged domains of pharyngeal epithelial cells. Microbial Pathogenesis 2000; 28: 203–209
   PubMedGoogle Scholar
• Duling D.R. Simulation of multiple isotropic spin-trap EPR spectra. Journal of Magnetic Resonance Series B 1994; 104: 105–110
   PubMedGoogle Scholar
• Pedersen J.A. Handbook of EPR Spectra from Quinones and Quinols. CRC Press, Boca Raton 1985
   Google Scholar
• Nagle J.F., Wilkinson D.A. Lecithin bilayers density measurement and molecular interactions. Biophysical Journal 1978; 23: 159–175
   PubMed Web of Science ®Google Scholar
• Knoll W. Volume determination of deuterated dimyristoyl lecitin by mass and scattering length densitometry. Chemistry and Physics of Lipids 1981; 28: 337–346
   Google Scholar
• Alegría A.E., Garcia C., Santiago G., Collazo G., Morant J. Intramolecular hydrogen bonding in hydroxylated semiquinones inhibits semiquinone-Mg2+ complex formation. Journal of the Chemical Society Perkin Transactions 2 2000; 1569–1573
   Google Scholar
• Alegría A.E., Lópes M., Guevara N. Thermodynamics of semiquinone disproportionation in aqueous buffer. Journal of the Chemical Society, Faraday Transactions 1996; 92: 4965–4968
   Google Scholar
• Ansell M.F., Nash B.W., Wilson D.A. Preparation of p-benzoquinones. Journal of the Chemical Society 1963; 3028–3036
   Google Scholar
• Caffrey M., Feigenson G.W. Influence of metal ions on the phase properties of phosphatidic acid in combination with natural and synthetic phosphatidylcholines: an X-ray diffraction study using synchrotron radiation. Biochemistry 1984; 23: 323–331
   PubMedGoogle Scholar
• Kinkaid A., Othman R., Voysey J., Wilton D.C. Phospholipase D and phosphatidic acid enhance the hydrolysis of phospholipids in vesicles and in cell membranes by human secreted phospholipase A2. Biochimica et Biophysica Acta 1998; 1390: 173–185
   PubMedGoogle Scholar
• Mitrakos P., Macdonald P.M. Nucleotide chain length and the morphology of complexes with cationic amphiphiles: (31)P-NMR observations. Biochimica et Biophysica Acta 2000; 1463: 355–373
   PubMedGoogle Scholar
• J. Rosing, H. Speijer, R.F. Zwaal. Prothrombin activation on phospholipid membranes with positive electrostatic potential. Biochemistry 1988; 27: 8–11
   PubMedGoogle Scholar
• Grivet J. Accurate numerical approximation to the Gauss-Lorentz lineshape. Journal of Magnetic Resonance 1997; 125: 102–106
   PubMedGoogle Scholar
• Land E.J., Mukherjee T., Swallow J. Reduction of naphthazarin molecule as studied by pulse radiolysis. Journal of the Chemical Society, Faraday Transactions 1983; 79: 391–404
   Google Scholar
• Bailey S.I., Ritchie I.M. A cyclic voltammetric study of the aqueous electrochemistry of some quinones. Electrochimica Acta 1985; 30: 3–12
   Web of Science ®Google Scholar
• Mukherjee T., Swallow A.J., Guyan P.M., Bruce J.M. One- and two-electron reduction or quinizarin and 5-methoxyquinizarin: a pulse radiolysis study. Journal of the Chemical Society, Faraday Transactions 1990; 86: 1483–1491
   Google Scholar
• Richter H.W. Pulse radiolysis of 4-tert-butyl-1,2-dihydroxybenzene and 4-tert-butyl-1,2-quinone. Journal of Physical Chemistry 1979; 83: 1123–1129
   Google Scholar
• Kalyanaraman B. Characterization of o-semiquinone radicals in biological systems. Methods in Enzymology 1990; 186: 333–343
   PubMed Web of Science ®Google Scholar
• Smejtek P., Wang S. Adsorption to dipalmitoylphosphatidylcholine membranes in gel and fluid state: pentachlorophenolate, dipicrylamine, and tetraphenylborate. Biophysical Journal 1990; 58: 1285–1294
   PubMedGoogle Scholar
• Flewelling R.F., Hubbell W.L. The membrane dipole potential in a total membrane potential model. Applications to hydrophobic ion interactions with membranes. Biophysical Journal 1986; 49: 541–552
   PubMedGoogle Scholar
• Brock W., Stark G., Jordan P.C. 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. Biophysical Chemistry 1981; 13: 329–348
   PubMedGoogle Scholar
• Bailey S.I., Ritchie I.M. A cyclic voltammetric study of the aqueous electrochemistry of some quinones. Electrochimica Acta 1985; 30: 3–12
   Web of Science ®Google Scholar
• Land E.J., Mukherjee T., Swallow A.J., Bruce J.M. Reduction of the naphthazarin molecule as studied by pulse radiolysis. Part 2. Second one-electron step. Journal of the Chemical Society, Faraday Transactions 1983; 179: 405–415
   Google Scholar
• Havelkova L., Bartusek M. Complexes of boric acid with o-diphenols. Collection of Czechoslovak Chemical Communications 1968; 33: 4188–4197
   Google Scholar
• Kiss T., Sorago I., Martin R.B. Complexes of 3,4-dihydroxyphenyl derivates. 9. Al3+ binding to catecholamines and tiron. Journal of the American Chemical Society 1989; 111: 3611–3614
   Web of Science ®Google Scholar
• Liebler D.C., Burr J.A. Antioxidant reactions of alpha-tocopherolhydroquinone. Lipids 2000; 35: 1045–1047
   PubMed Web of Science ®Google Scholar
• Soucek P., Ivan G., Pavel S. Effect of the microsomal system on interconversions between hydroquinone, benzoquinone, oxygen activation, and lipid peroxidation. Chemico-Biological Interactions 2000; 126: 45–61
   PubMedGoogle Scholar
• Cadenas E. Antioxidant and prooxidant functions of DT-diaphorase in quinone metabolism. Biochemical Pharmacology 1995; 49: 127–140
   PubMed Web of Science ®Google Scholar
• Alegría A.E., Santiago G. Structural and hydrophylicity requirements in quinone-induced lipid peroxidation of phosphatidylcholine vesicles. Toxicological and Environmental Chemistry 1998; 65: 185–202
   Google Scholar
• Ilan Y.A., Czapski G., Meisel D. The one-electron transfer redox potentials of free radicals. I. The oxygen/superoxide system. Biochimica et Biophysica Acta 1976; 430: 209–224
   PubMed Web of Science ®Google Scholar