Mitochondria as subcellular targets for clinically useful anthracyclines.

[1]  A. Cederbaum,et al.  Mitochondrial permeability transition induced by 1-hydroxyethyl radical. , 2000, Free radical biology & medicine.

[2]  J. Jaffrezou,et al.  Implication of radical oxygen species in ceramide generation, c-Jun N-terminal kinase activation and apoptosis induced by daunorubicin. , 1999, Molecular pharmacology.

[3]  Seamus J. Martin,et al.  Regulation of Apoptotic Protease Activating Factor-1 Oligomerization and Apoptosis by the WD-40 Repeat Region* , 1999, The Journal of Biological Chemistry.

[4]  C. Palmeira,et al.  Cardioselective and cumulative oxidation of mitochondrial DNA following subchronic doxorubicin administration. , 1999, Biochimica et biophysica acta.

[5]  D. Wallace Mitochondrial diseases in man and mouse. , 1999, Science.

[6]  Jianjie Ma,et al.  Mitochondrial Depolarization Accompanies Cytochrome cRelease During Apoptosis in PC6 Cells* , 1999, The Journal of Biological Chemistry.

[7]  D. S. St. Clair,et al.  Manganese superoxide dismutase protects mitochondrial complex I against adriamycin-induced cardiomyopathy in transgenic mice. , 1999, Archives of biochemistry and biophysics.

[8]  Emad S. Alnemri,et al.  Ordering the Cytochrome c–initiated Caspase Cascade: Hierarchical Activation of Caspases-2, -3, -6, -7, -8, and -10 in a Caspase-9–dependent Manner , 1999, The Journal of cell biology.

[9]  G. Salvesen,et al.  Caspase-14 Is a Novel Developmentally Regulated Protease* , 1998, The Journal of Biological Chemistry.

[10]  G. Lenaz Role of mitochondria in oxidative stress and ageing. , 1998, Biochimica et biophysica acta.

[11]  B. Ames,et al.  The free radical theory of aging matures. , 1998, Physiological reviews.

[12]  L. Gille,et al.  The Exogenous NADH Dehydrogenase of Heart Mitochondria Is the Key Enzyme Responsible for Selective Cardiotoxicity of Anthracyclines , 1998, Zeitschrift fur Naturforschung. C, Journal of biosciences.

[13]  L. Szweda,et al.  Cardiac reperfusion injury: aging, lipid peroxidation, and mitochondrial dysfunction. , 1998, Proceedings of the National Academy of Sciences of the United States of America.

[14]  John Calvin Reed,et al.  Cytochrome c: Can't Live with It—Can't Live without It , 1997, Cell.

[15]  A. E. Alegria,et al.  Adriamycin and daunomycin semiquinone membrane/buffer partition constants using the spin-broadening technique. , 1997, Archives of biochemistry and biophysics.

[16]  C. Palmeira,et al.  Preferential oxidation of cardiac mitochondrial DNA following acute intoxication with doxorubicin. , 1997, Biochimica et biophysica acta.

[17]  Xiaodong Wang,et al.  Apaf-1, a Human Protein Homologous to C. elegans CED-4, Participates in Cytochrome c–Dependent Activation of Caspase-3 , 1997, Cell.

[18]  B. Robinson,et al.  Excessive formation of hydroxyl radicals and aldehydic lipid peroxidation products in cultured skin fibroblasts from patients with complex I deficiency. , 1997, The Journal of clinical investigation.

[19]  T. Horie,et al.  Detection of Phosphatidylcholine Hydroperoxide Produced in the Heart of the Doxorubicin Administered Mouse , 1997 .

[20]  B. Van Houten,et al.  Mitochondrial DNA damage is more extensive and persists longer than nuclear DNA damage in human cells following oxidative stress. , 1997, Proceedings of the National Academy of Sciences of the United States of America.

[21]  D. S. St. Clair,et al.  The protective role of manganese superoxide dismutase against adriamycin-induced acute cardiac toxicity in transgenic mice. , 1996, The Journal of clinical investigation.

[22]  B. Robinson,et al.  Mitochondrial complex I deficiency leads to increased production of superoxide radicals and induction of superoxide dismutase. , 1996, The Journal of clinical investigation.

[23]  T. Robak,et al.  Interaction of anthracyclines with human erythrocytes at hyperthermic temperature , 1996 .

[24]  K. Wallace,et al.  Dose-dependent increase in sensitivity to calcium-induced mitochondrial dysfunction and cardiomyocyte cell injury by doxorubicin. , 1996, Journal of molecular and cellular cardiology.

[25]  K. Schönheit,et al.  Oxidation of cytosolic NADH via complex I of heart mitochondria. , 1996, Archives of biochemistry and biophysics.

[26]  G. Laurent,et al.  Daunorubicin-induced internucleosomal DNA fragmentation in acute myeloid cell lines. , 1996, Leukemia.

[27]  G. Link,et al.  Role of iron in the potentiation of anthracycline cardiotoxicity: identification of heart cell mitochondria as a major site of iron-anthracycline interaction. , 1996, The Journal of laboratory and clinical medicine.

[28]  C. Epstein,et al.  Dilated cardiomyopathy and neonatal lethality in mutant mice lacking manganese superoxide dismutase , 1995, Nature Genetics.

[29]  B. Ames,et al.  Mitochondrial decay in aging. , 1995, Biochimica et biophysica acta.

[30]  A. Cavaliere,et al.  Secondary alcohol metabolites mediate iron delocalization in cytosolic fractions of myocardial biopsies exposed to anticancer anthracyclines. Novel linkage between anthracycline metabolism and iron-induced cardiotoxicity. , 1995, The Journal of clinical investigation.

[31]  T. Horie,et al.  Fluorescent Substances and High Molecular Weight Protein Aggregates Formed in Rat Heart Mitochondria upon Doxorubicin‐induced Lipid Peroxidation , 1995, The Journal of pharmacy and pharmacology.

[32]  E. Cadenas,et al.  Hydroxyl radical generation during mitochondrial electron transfer and the formation of 8-hydroxydesoxyguanosine in mitochondrial DNA. , 1995, Archives of biochemistry and biophysics.

[33]  T. Henry,et al.  Disruption of mitochondrial calcium homeostasis following chronic doxorubicin administration. , 1994, Toxicology and applied pharmacology.

[34]  B. Ames,et al.  Oxidative damage and mitochondrial decay in aging. , 1994, Proceedings of the National Academy of Sciences of the United States of America.

[35]  D. Wallace,et al.  Mitochondrial DNA sequence variation in human evolution and disease. , 1994, Proceedings of the National Academy of Sciences of the United States of America.

[36]  K. Orita,et al.  Alterations of membrane fluidity in K562 cells exposed to the anticancer drug adriamycin. , 1994, Research Communications in Molecular Pathology and Pharmacology.

[37]  L. Ji,et al.  Effects of Adriamycin on heart mitochondrial function in rested and exercised rats. , 1994, Biochemical pharmacology.

[38]  B. Ames,et al.  Oxidants, antioxidants, and the degenerative diseases of aging. , 1993, Proceedings of the National Academy of Sciences of the United States of America.

[39]  G. Link,et al.  Anthracycline toxicity is potentiated by iron and inhibited by deferoxamine: studies in rat heart cells in culture. , 1993, The Journal of laboratory and clinical medicine.

[40]  K. Wallace,et al.  Selective activation of the sodium-independent, cyclosporin A-sensitive calcium pore of cardiac mitochondria by doxorubicin. , 1993, Toxicology and applied pharmacology.

[41]  J. Ruysschaert,et al.  In-vivo and in-vitro mitochondrial membrane damages induced in mice by adriamycin and derivatives. , 1993, Biochimica et biophysica acta.

[42]  A. Muga,et al.  The interaction of daunomycin with model membranes. Effect of the lipid physical state and the lipid composition. , 1993, European journal of biochemistry.

[43]  L. Papadopoulou,et al.  Mitochondrial cytochrome c oxidase as a target site for daunomycin in K-562 cells and heart tissue. , 1993, Cancer research.

[44]  A. Piskunov,et al.  Role of quinone-iron(III) interaction in NADPH-dependent enzymatic generation of hydroxyl radicals. , 1992, Biochemistry.

[45]  F. L. Crane,et al.  Inhibition of transplasma membrane electron transport by transferrin-adriamycin conjugates. , 1992, Biochimica et biophysica acta.

[46]  J. González-Ros,et al.  Different distribution of daunomycin in plasma membranes from drug-sensitive and drug-resistant P388 leukemia cells. , 1992, Biochimica et biophysica acta.

[47]  T. Hidaka,et al.  Electron spin resonance studies on the mechanism of adriamycin-induced heart mitochondrial damages. , 1991, Cancer research.

[48]  R. Mason,et al.  An electron paramagnetic resonance study of the interactions between the adriamycin semiquinone, hydrogen peroxide, iron-chelators, and radical scavengers. , 1991, Archives of biochemistry and biophysics.

[49]  P Louisot,et al.  Mitochondrial contact sites. Lipid composition and dynamics. , 1990, The Journal of biological chemistry.

[50]  R. Olson,et al.  Doxorubicin cardiotoxicity: analysis of prevailing hypotheses , 1990, FASEB journal : official publication of the Federation of American Societies for Experimental Biology.

[51]  J. González-Ros,et al.  Role of membrane lipids in the interaction of daunomycin with plasma membranes from tumor cells: implications in drug-resistance phenomena. , 1990, Biochemistry.

[52]  A. Williams,et al.  Patterns of interaction between anthraquinone drugs and the calcium-release channel from cardiac sarcoplasmic reticulum. , 1990, Circulation research.

[53]  P. Riesz,et al.  Free radicals induced by adriamycin-sensitive and adriamycin-resistant cells: a spin-trapping study. , 1989, Biochemistry.

[54]  E. Land,et al.  One-electron reduction of adriamycin and daunomycin: short-term stability of the semiquinones. , 1989, Archives of biochemistry and biophysics.

[55]  D. Katz,et al.  Structural requirements for anthracycline-induced cardiotoxicity and antitumor effects. , 1989, Toxicology and applied pharmacology.

[56]  B. Ames,et al.  Normal oxidative damage to mitochondrial and nuclear DNA is extensive. , 1988, Proceedings of the National Academy of Sciences of the United States of America.

[57]  H. Nohl Identification of the site of adriamycin-activation in the heart cell. , 1988, Biochemical pharmacology.

[58]  J. Davey,et al.  The iron(III)-adriamycin complex inhibits cytochrome c oxidase before its inactivation. , 1988, The Biochemical journal.

[59]  P. M. Sokolove,et al.  Na+-independent release of Ca2+ from rat heart mitochondria. Induction by adriamycin aglycone. , 1988, Biochemical pharmacology.

[60]  H. Nohl Demonstration of the existence of an organo-specific NADH dehydrogenase in heart mitochondria. , 1987, European journal of biochemistry.

[61]  C. Winterbourn,et al.  Radical-driven Fenton reactions: studies with paraquat, adriamycin, and anthraquinone 6-sulfonate and citrate, ATP, ADP, and pyrophosphate iron chelates. , 1987, Archives of biochemistry and biophysics.

[62]  L. Landi,et al.  Protective effect of endogenous coenzyme Q on both lipid peroxidation and respiratory chain inactivation induced by an adriamycin-iron complex. , 1987, Biochemical and biophysical research communications.

[63]  J. Zweier,et al.  5-Iminodaunomycin. An anthracycline with unique properties. , 1987, The Journal of biological chemistry.

[64]  G. Batist,et al.  Differential formation of hydroxyl radicals by adriamycin in sensitive and resistant MCF-7 human breast tumor cells: implications for the mechanism of action. , 1987, Biochemistry.

[65]  M. Tachibana,et al.  EPR studies of copper(II) and cobalt(II) complexes of adriamycin. , 1987, Journal of inorganic biochemistry.

[66]  Y. Mariam,et al.  A free radical scavenger role for daunomycin: inhibition of nonenzymatic oxidation of NADH. , 1987, Biochemical and Biophysical Research Communications - BBRC.

[67]  J. Vanderkooi,et al.  Anthracycline binding to synthetic and natural membranes. A study using resonance energy transfer. , 1986, Biochemistry.

[68]  E. Mimnaugh,et al.  A possible role for membrane lipid peroxidation in anthracycline nephrotoxicity. , 1986, Biochemical pharmacology.

[69]  B. de Kruijff,et al.  Cytofluorescence detection of adriamycin-mitochondria interactions in isolated, perfused rat heart. , 1986, Biochimica et biophysica acta.

[70]  J. Doroshow,et al.  Redox cycling of anthracyclines by cardiac mitochondria. I. Anthracycline radical formation by NADH dehydrogenase. , 1986, The Journal of biological chemistry.

[71]  P. Singal,et al.  Adriamycin stimulates low-affinity Ca2+ binding and lipid peroxidation but depresses myocardial function. , 1986, The American journal of physiology.

[72]  T. E. Thompson,et al.  Physical and chemical modifications of adriamycin:iron complex by phospholipid bilayers. , 1986, Cancer Research.

[73]  A. Garnier-Suillerot,et al.  Interaction of adriamycin with cardiolipin-containing vesicles. Evidence of an embedded site for the dihydroanthraquinone moiety. , 1986, Biochimica et biophysica acta.

[74]  J. Doroshow,et al.  Effect of doxorubicin-enhanced hydrogen peroxide and hydroxyl radical formation on calcium sequestration by cardiac sarcoplasmic reticulum. , 1985, Biochemical and biophysical research communications.

[75]  J. Zweier,et al.  Characterization of the cycle of iron-mediated electron transfer from Adriamycin to molecular oxygen. , 1985, The Journal of biological chemistry.

[76]  E. Land,et al.  Possible intermediates in the action of adriamycin--a pulse radiolysis study. , 1985, British Journal of Cancer.

[77]  A. J. Swallow,et al.  Reactions of the semiquinone free radicals of anti‐tumour agents with oxygen and iron complexes , 1985, FEBS letters.

[78]  B. de Kruijff,et al.  The interaction of adriamycin with cardiolipin in model and rat liver mitochondrial membranes. , 1984, Biochimica et biophysica acta.

[79]  C. Winterbourn,et al.  Hydroxyl radical production from hydrogen peroxide and enzymatically generated paraquat radicals: catalytic requirements and oxygen dependence. , 1984, Archives of biochemistry and biophysics.

[80]  C. Winterbourn,et al.  Chelated iron-catalyzed OH. formation from paraquat radicals and H2O2: mechanism of formate oxidation. , 1984, Archives of biochemistry and biophysics.

[81]  C. Myers,et al.  Hydroxyl radical production and DNA damage induced by anthracycline‐iron complex , 1984, FEBS letters.

[82]  Y. Lion,et al.  Adriamycin and derivatives interaction with the mitochondrial membrane: O2 consumption and free radicals formation. , 1984, Research communications in chemical pathology and pharmacology.

[83]  L. Gianni,et al.  Oxidative destruction of DNA by the adriamycin-iron complex. , 1984, Biochemistry.

[84]  H. Nohl,et al.  OH.-generation by adriamycin semiquinone and H2O2; an explanation for the cardiotoxicity of anthracycline antibiotics. , 1983, Biochemical and biophysical research communications.

[85]  D. J. Reed,et al.  Depletion in vitro of mitochondrial glutathione in rat hepatocytes and enhancement of lipid peroxidation by adriamycin and 1,3-bis(2-chloroethyl)-1-nitrosourea (BCNU). , 1983, Biochemical pharmacology.

[86]  J. Doroshow,et al.  Mitochondrial NADH dehydrogenase‐catalyzed oxygen radical production by adriamycin, and the relative inactivity of 5‐iminodaunorubicin , 1983, FEBS letters.

[87]  J. Doroshow Effect of anthracycline antibiotics on oxygen radical formation in rat heart. , 1983, Cancer research.

[88]  C. Winterbourn,et al.  Deoxyribose breakdown by the adriamycin semiquinone and H2O2: evidence for hydroxyl radical participation , 1982, FEBS letters.

[89]  C. Simone,et al.  Oxidative destruction of erythrocyte ghost membranes catalyzed by the doxorubicin-iron complex. , 1982, Biochemistry.

[90]  E. Acton,et al.  Further studies on the generation of reactive oxygen species from activated anthracyclines and the relationship to cytotoxic action and cardiotoxic effects. , 1982, Biochemical pharmacology.

[91]  R. Brasseur,et al.  Adriamycin inactivates cytochrome c oxidase by exclusion of the enzyme from its cardiolipin essential environment. , 1982, Biochemical and biophysical research communications.

[92]  E. Mimnaugh,et al.  Stimulation by adriamycin of rat heart and liver microsomal NADPH-dependent lipid peroxidation. , 1981, Biochemical pharmacology.

[93]  W. Haseltine,et al.  Reduction of adriamycin to a semiquinone-free radical by NADPH cytochrome P-450 reductase produces DNA cleavage in a reaction mediated by molecular oxygen. , 1981, The Journal of biological chemistry.

[94]  D. E. Green,et al.  Cardiolipin requirement for electron transfer in complex I and III of the mitochondrial respiratory chain. , 1981, The Journal of biological chemistry.

[95]  E. Goormaghtigh,et al.  Evidence of a complex between adriamycin derivatives and cardiolipin: possible role in cardiotoxicity. , 1980, Biochemical pharmacology.

[96]  D. E. Green,et al.  Cardiolipin requirement by cytochrome oxidase and the catalytic role of phospholipid. , 1980, Biochemical and biophysical research communications.

[97]  V. Ferrans,et al.  Cardiac disease induced by chronic adriamycin administration in dogs and an evaluation of vitamin E and selenium as cardioprotectants. , 1980, The American journal of pathology.

[98]  E. Acton,et al.  Diminished superoxide anion generation by reduced 5-iminodaunorubicin relative to daunorubicin and the relationship to cardiotoxicity of the anthracycline antitumor agents. , 1979, Biochemical pharmacology.

[99]  B Chance,et al.  Hydroperoxide metabolism in mammalian organs. , 1979, Physiological reviews.

[100]  A. Verkleij,et al.  Polymorphic phase behaviour of cardiolipin as detected by 31P NMR and freeze-fracture techniques. Effects of calcium, dibucaine and chlorpromazine. , 1978, Biochimica et biophysica acta.

[101]  R. Goldman,et al.  A differential interaction of daunomycin, adriamycin and their derivatives with human erythrocytes and phospholipid bilayers. , 1978, Biochimica et biophysica acta.

[102]  Ferrans Vj Overview of cardiac pathology in relation to anthracycline cardiotoxicity. , 1978, Cancer treatment reports.

[103]  W. S. Thayer Adriamycin stimulated superoxide formation in submitochondrial particles. , 1977, Chemico-biological interactions.

[104]  K. Handa,et al.  Electron spin resonance study on the mode of generation of free radicals of daunomycin, adriamycin, and carboquone in NAD(P)H-microsome system. , 1977, Gan.

[105]  I. Ifrim,et al.  Adriamycin: the role of lipid peroxidation in cardiac toxicity and tumor response. , 1977, Science.

[106]  K. C. Majumdar,et al.  Strand scission of DNA by bound adriamycin and daunorubicin in the presence of reducing agents. , 1977, Biochemical and biophysical research communications.

[107]  C. Myers,et al.  Adriamycin: amelioration of toxicity by alpha-tocopherol. , 1976, Cancer treatment reports.

[108]  F. Formelli,et al.  Synthesis and antitumor properties of new glycosides of daunomycinone and adriamycinone , 1975 .

[109]  F. Formelli,et al.  Synthesis and antitumor properties of new glycosides of daunomycinone and adriamycinone. , 1975, Journal of medicinal chemistry.

[110]  J. Pitha,et al.  A clinicopathologic analysis of adriamycin cardiotoxicity , 1973, Cancer.

[111]  I. Fridovich,et al.  Mitochondrial superoxide simutase. Site of synthesis and intramitochondrial localization. , 1973, The Journal of biological chemistry.

[112]  T. Iyanagi,et al.  One-electron-transfer reactions in biochemical systems. V. Difference in the mechanism of quinone reduction by the NADH dehydrogenase and the NAD(P)H dehydrogenase (DT-diaphorase). , 1970, Biochimica et biophysica acta.

[113]  S. Nakamura,et al.  One-electron transfer reactions in biochemical systems. IV. A mixed mechanism in the reaction of milk xanthine oxidase with electron acceptors. , 1969, Biochimica et biophysica acta.

[114]  A. Starkov,et al.  Mitochondrial targets of drug toxicity. , 2000, Annual review of pharmacology and toxicology.

[115]  L. Gille,et al.  Analyses of the molecular mechanism of adriamycin-induced cardiotoxicity. , 1997, Free radical biology & medicine.

[116]  B. Halliwell,et al.  The definition and measurement of antioxidants in biological systems. , 1995, Free radical biology & medicine.

[117]  M. Dizdaroglu Chemical determination of free radical-induced damage to DNA. , 1991, Free radical biology & medicine.

[118]  R. Denton,et al.  Ca2+ as a second messenger within mitochondria of the heart and other tissues. , 1990, Annual review of physiology.

[119]  J. Robert Pharmacocinétique des nouvelles anthracyclines. , 1988 .

[120]  A. Tomasi,et al.  Spin trapping of free radical species produced during the microsomal metabolism of ethanol. , 1988, Chemico-biological interactions.

[121]  R. Brasseur,et al.  Mechanism of inhibition of mitochondrial enzymatic complex I-III by adriamycin derivatives. , 1986, Biochimica et biophysica acta.

[122]  B. Halliwell,et al.  Doxorubicin-dependent lipid peroxidation at low partial pressures of O2. , 1985, Journal of free radicals in biology & medicine.

[123]  D. Pietronigro,et al.  Spontaneous generation of adriamycin semiquinone radicals at physiologic pH. , 1979, Physiological chemistry and physics.