Ortho-quinone-enhanced ascorbate oxidation. Combined roles of lipid charge and the magnesium cation

References

• Montano , MM , Bianco , NR , Deng , H , Wittmann , BM , Chaplin , LC and Katzenellenbogen , BS . 2005 . Estrogen receptor regulation of quinone reductase in breast cancer: Implications for estrogen-induced breast tumor growth and therapeutic uses of tamoxifen . Front. Biosci. , 10 : 1440 – 1461 .
   PubMedGoogle Scholar
• Danson , S , Ward , TH , Butler , J and Ranson , M . 2004 . DT-diaphorase: A target for new anticancer drugs . Cancer Treat. Rev. , 30 : 437 – 449 .
   PubMed Web of Science ®Google Scholar
• Xue , W and Warshawsky , D . 2005 . Metabolic activation of polycyclic and heterocyclic aromatic hydrocarbons and DNA damage: A review . Toxicol. Appl. Pharmacol. , 206 : 73 – 93 .
   PubMed Web of Science ®Google Scholar
• Ogawa , N , Asanuma , M , Miyazaki , I , Diaz-Corrales , FJ and Miyoshi , K . 2005 . L-DOPA treatment from the viewpoint of neuroprotection. Possible mechanism of specific and progressive dopaminergic neuronal death in Parkinson's disease . J. Neurol. , 252 ( Suppl 4 ) : IV23 – IV31 .
   PubMed Web of Science ®Google Scholar
• Stites , TE , Mitchell , AE and Rucker , RB . 2000 . Physiological importance of quinoenzymes and the o-quinone family of cofactors . J. Nutr. , 130 : 719 – 727 .
   PubMed Web of Science ®Google Scholar
• Zhao , Z , Kosinska , W , Khmelnitsky , M , Cavalieri , EL , Rogan , EG , Chakravarti , D , Sacks , PG and Guttenplan , JB . 2006 . Mutagenic activity of 4-hydroxyestradiol, but not 2-hydroxyestradiol, in BB rat2 embryonic cells', and the mutational spectrum of 4-hydroxyestradiol . Chem. Res. Toxicol. , 19 : 475 – 479 .
   PubMed Web of Science ®Google Scholar
• Alegria , AE , Sanchez-Cruz , P and Rivas , L . 2004 . Alkaline-earth cations enhance ortho-quinone-catalyzed ascorbate oxidation . Free Radic. Biol. Med. , 37 : 1631 – 1639 .
   PubMed Web of Science ®Google Scholar
• Kalyanaraman , B , Sealy , RC and Liehr , JG . 1989 . Characterization of semiquinone free radicals formed from stilbene catechol estrogens. An ESR spin stabilization and spin trapping study . J. Biol. Chem. , 264 : 11014 – 11019 .
   PubMedGoogle Scholar
• Kalyanaraman , B , Premovic , PI and Sealy , RC . 1987 . Semiquinone anion radicals from addition of amino acids, peptides, and proteins to quinones derived from oxidation of catechols and catecholamines. An ESR spin stabilization study . J. Biol. Chem. , 262 : 11080 – 11087 .
   PubMed Web of Science ®Google Scholar
• Kalyanaraman , B , Korytowski , W , Pilas , B , Sarna , T , Land , EJ and Truscott , TG . 1988 . Reaction between ortho-semiquinones and oxygen: Pulse radiolysis, electron spin resonance, and oxygen uptake studies . Arch. Biochem. Biophys. , 266 : 277 – 284 .
   PubMed Web of Science ®Google Scholar
• Sato , A , Takagi , K , Kano , K , Kato , N , Duine , JA and Ikeda , T . 2001 . Ca(2+) stabilizes the semiquinone radical of pyrroloquinoline quinone . Biochem. J. , 357 : 893 – 898 .
   PubMed Web of Science ®Google Scholar
• Lebedev , AV , Ivanova , MV and Ruuge , EK . 2003 . How do calcium ions induce free radical oxidation of hydroxy-l,4-naphthoquinone? Ca2+ stabilizes the naphthosemiquinone anion-radical of echinochrome A . Arch. Biochem. Biophys. , 413 : 191 – 198 .
   PubMed Web of Science ®Google Scholar
• Planchon , SM , Wuerzberger , S , Frydman , B , Witiak , DT , Hutson , P , Church , DR , Wilding , G and Boothman , DA . 1995 . Beta-lapachone-mediated apoptosis in human promyelocytic leukemia (HL-60) and human prostate cancer cells: A p53-independent response . Cancer Res. , 55 : 3706 – 3711 .
   PubMed Web of Science ®Google Scholar
• Wuerzberger , SM , Pink , JJ , Planchon , SM , Byers , KL , Bornmann , WG and Boothman , DA . 1998 . Induction of apoptosis in MCF-7: WS8 breast cancer cells by beta-lapachone . Cancer Res. , 58 : 1876 – 1885 .
   PubMed Web of Science ®Google Scholar
• Li , CJ , Wang , C and Pardee , AB . 1995 . Induction of apoptosis by beta-lapachone in human prostate cancer cells . Cancer Res. , 55 : 3712 – 3715 .
   PubMed Web of Science ®Google Scholar
• Lee , JI , Choi , DY , Chung , HS , Seo , HG , Woo , HJ , Choi , BT and Choi , YH . 2006 . Beta-lapachone induces growth inhibition and apoptosis in Bladder cancer cells by modulation of Bcl-2 family and activation of caspases . Exp. Oncol. , 28 : 30 – 35 .
   PubMedGoogle Scholar
• Reinicke , KE , Bey , EA , Bentle , MS , Pink , JJ , Ingalls , ST , Hoppel , CL , Misico , RI , Arzac , GM , Burton , G Bornmann , WG . 2005 . Development of beta-lapachone prodrugs for therapy against human cancer cells with elevated NAD(P)H: Quinone oxidoreductase 1 levels . Clin. Cancer Res. , 11 : 3055 – 3064 .
   PubMed Web of Science ®Google Scholar
• Buettner , GR . 1988 . In the absence of catalytic metals ascorbate does not autoxidize at pH 7: Ascorbate as a test for catalytic metals . J. Biochem. Biophys. Methods , 16 : 27 – 40 .
   PubMedGoogle Scholar
• Alegria , AE , Rivera , S , Hernandez , M , Ufret , R and Morales , M . 1993 . Membrane-buffer partition coefficients of semiquinones using the spin- broadening technique . J. Chem. Soc. Faraday Tran. , 89 : 3773 – 3777 .
   Google Scholar
• Alegria , AE , Rivera , L , Cordones , E , Castro , V and Sanchez-Cruz , P . 2002 . Role of membrane charge and setftiquinone structure on oxygen consumption rates . J. Chem. Soc. Perkin Trans. , 2 : 1823 – 1828 .
   Google Scholar
• Mayer , LD , Hope , MJ and Cullis , PR . 1986 . Vesicles of variable sizes produced by a rapid extrusion procedure . Biochim. Biophys. Acta. , 858 : 161 – 168 .
   PubMed Web of Science ®Google Scholar
• Alegría , AE , López , M and Guevara , N . 1996 . Thermodynamics of semiquinone disproportionation in aqueous buffer . J. Chem. Soc. Faraday Trans. , 92 : 4965 – 4968 .
   Google Scholar
• Roginsky , VA , Pisarenko , LM , Bors , W and Michel , C . 1999 . The kinetics and thermodynamics of quinone- semiquinone-hydroquinone systems under physiological conditions . J. Chem. Soc. Perkin Trans. , 2 : 871 – 876 .
   Google Scholar
• Duling , DR . 1994 . Simulation of multiple isotropic spin-trap EPR spectra . J. Mag. Reson., Ser. B , 104 : 105 – 110 .
   PubMed Web of Science ®Google Scholar
• Nagle , JF and Wilkinson , DA . 1978 . Lecithin bilayers. Density measurement and molecular interactions . Biophys. J. , 23 : 159 – 175 .
   PubMed Web of Science ®Google Scholar
• Knoll , W . 1981 . Volume determination of deuterated dirnyristoyllecithin by mass and scattering length densiometry . Chem. Phys. Lip. , 28 : 337 – 345 .
   Google Scholar
• Schumpe , A , Adler , I and Deckwer , WD . 1978 . Solubility of oxygen in electrolyte solutions . Biotech. Bioeng. , 20 : 145 – 150 .
   Google Scholar
• Lang , W and Zander , R . 1986 . Salting-out of oxygen from aqueous electrolyte solutions: Prediction and measurement . Ind. Eng. Chem. Fundam. , 25 : 775 – 782 .
   Google Scholar
• Roginsky , VA , Barsukova , TK , Bruchelt , G and Stegmann , HB . 1998 . Kinetics of redox interaction between substituted 1,4-benzoquinones and ascorbate under aerobic conditions: Critical phenomena . Free Rad. Res. , 29 : 115 – 125 .
   PubMed Web of Science ®Google Scholar
• Maslowska , J and Owczarek , A . 1983 . Studies on ascorbate complexes of metal ions of the beryllium group by the method of potentiometric surfaces . Pol. J. Chem. , 57 : 719 – 726 .
   Google Scholar
• Roginsky , VA , Barsukova , TK and Stegmann , HB . 1999 . Kinetics of redox interaction between substituted quinones and ascorbate under aerobic conditions . Chem. Biol. Interact. , 121 : 177 – 197 .
   PubMed Web of Science ®Google Scholar
• Marcus , Y . 1985 . Ion solvation , New York : John Wiley .
   Google Scholar
• Stevenson , GR and Alegria , AE . 1976 . Rates of ion pair formation and dissociation and of electron exchange between free ion and neutral molecule in examethylphosphoramide . Phys. Chem. , 80 : 69 – 73 .
   Google Scholar