Photochemical interactions of methylene blue and analogues with DNA and other biological substrates.

The light-induced reactions of methylene blue and related phenothiazinium dyes with biological substrates are described. The properties of the excited states of the dyes, their reactions with nucleic acids and their photosensitised chemical modifications of nucleic acid bases are examined. Reports on phenothiazinium dye-induced damage to proteins, lipids, biological membranes, organelles, viruses, bacteria, mammalian cells and carcinomas are reviewed.

[1]  A. Kaisary Assessment of radiotherapy in invasive bladder carcinoma using in vivo methylene blue staining technique. , 1986, Urology.

[2]  B. Epe,et al.  Singlet oxygen as an ultimately reactive species in Salmonella typhimurium DNA damage induced by methylene blue/visible light. , 1989, Carcinogenesis.

[3]  B. Lambrecht,et al.  Photoinactivation of Viruses in Human Fresh Plasma by Phenothiazine Dyes in Combination with Visible Light , 1991, Vox sanguinis.

[4]  B. Epe,et al.  DNA damage by oxygen radicals and excited state species: a comparative study using enzymatic probes in vitro. , 1988, Chemico-biological interactions.

[5]  D. Crothers,et al.  Interactions of heteroaromatic compounds with nucleic acids. 1. The influence of heteroatoms and polarizability on the base specificity of intercalating ligands. , 1975, European journal of biochemistry.

[6]  T. Ohno,et al.  Mechanistic aspects of the quenching of triplet methylene blue by organic reductants , 1982 .

[7]  H. Schmidt,et al.  ON THE ACRIDINE AND THIAZINE DYE SENSITIZED PHOTODYNAMIC INACTIVATION OF LYSOZYME—SINGLET OXYGEN SELF‐QUENCHING BY THE SENSITIZERS , 1981 .

[8]  Yuji Saito,et al.  NON‐CLOTTABLE FIBRINOGEN BY PHOTOOXIDATION IN BLOOD PLASMA , 1987, Photochemistry and Photobiology.

[9]  Takashi Ito,et al.  A SURVEY OF IN VIVO PHOTODYNAMIC ACTIVITY OF XANTHENES, THIAZINES, AND ACRIDINES IN YEAST CELLS , 1977 .

[10]  C. T. O'konski,et al.  A SPECTROSCOPIC STUDY OF METHYLENE BLUE MONOMER, DIMER, AND COMPLEXES WITH MONTMORILLONITE , 1963 .

[11]  R. W. Tuveson,et al.  Role of cloned carotenoid genes expressed in Escherichia coli in protecting against inactivation by near-UV light and specific phototoxic molecules , 1988, Journal of bacteriology.

[12]  S. Ameta,et al.  Use of an azur C‐EDTA system in a photogalvanic cell for solar energy conversion , 1991 .

[13]  A. Wand,et al.  Dye-sensitized photo-oxidation of enzymes. , 1985, The Biochemical journal.

[14]  R. S. Sinclair,et al.  SINGLET OXYGEN YIELDS AND RADICAL CONTRIBUTIONS IN THE DYE‐SENSITISED PHOTO‐OXIDATION IN METHANOL OF ESTERS OF POLYUNSATURATED FATTY ACIDS (OLEIC, LINOLEIC, LINOLENIC AND ARACHIDONIC) , 1988, Photochemistry and photobiology.

[15]  Robert H. Austin,et al.  Bending and twisting dynamics of short linear DNAs. Analysis of the triplet anisotropy decay of a 209 base pair fragment by Brownian simulation , 1989 .

[16]  W. Gill,et al.  In vivo mapping of bladder cancer (chromocystoscopy for in vivo detection of neoplastic urothelial surfaces). , 1984, Urology.

[17]  S. Steenken Electron-transfer-induced acidity/basicity and reactivity changes of purine and pyrimidine bases. Consequences of redox processes for DNA base pairs. , 1992, Free radical research communications.

[18]  N. Krinsky,et al.  EFFECT OF SINGLET OXYGEN QUENCHERS ON OXIDATIVE DAMAGE TO LIPOSOMES INITIATED BY PHOTOSENSITIZATION OR BY RADIOFREQUENCY DISCHARGE , 1974, Photochemistry and photobiology.

[19]  R. Devonshire,et al.  Methylene blue and the photodynamic therapy of superficial bladder cancer. , 1989, Journal of photochemistry and photobiology. B, Biology.

[20]  P. Kamat Photoelectrochemistry in colloidal systems. Part 2.—A photogalvanic cell based on TiO2 semiconductor colloid , 1985 .

[21]  E. M. Link,et al.  211At-methylene blue for targeted radiotherapy of human melanoma xenografts: treatment of cutaneous tumors and lymph node metastases. , 1992, Cancer research.

[22]  H. Jacob DNA REPAIR AFTER PHOTODYNAMIC TREATMENT OF PROTEUS MIRABILIS , 1975 .

[23]  J. Bellin Immunological Properties of Photodynamically Inactivated Tumour Cells , 1962, Nature.

[24]  J. Cadet,et al.  Mechanisms and Products of Photosensitized Degradation of Nucleic Acids and Related Model Compounds , 1983 .

[25]  B. Troche The methylene blue baby. , 1989, The New England journal of medicine.

[26]  A. Pardee,et al.  Photodynamic inactivation of free and vegatative bacteriophage T4. , 1967, Biochimica et biophysica acta.

[27]  H. Dunford,et al.  Kinetics of the oxidation of NADH by methylene blue in a closed system , 1991 .

[28]  H. Rosenkranz,et al.  Further observations on the photooxidation of DNA in the presence of riboflavin. , 1976, Biochimica et biophysica acta.

[29]  R. Mackay,et al.  Formation of H aggregates in thionine dye in water , 1984 .

[30]  G. Skinner,et al.  A kinetic study of the photochemical inactivation of adenylate kinases of Mycobacterium marinum and bovine heart mitochondria. , 1990, Biochimica et biophysica acta.

[31]  R. Floyd,et al.  Methylene blue plus light mediates 8-hydroxy 2'-deoxyguanosine formation in DNA preferentially over strand breakage. , 1990, Nucleic acids research.

[32]  T. Dubbelman,et al.  Photodynamic intramolecular crosslinking of myoglobin , 1984 .

[33]  C. Wallis,et al.  PHOTODYNAMIC INACTIVATION OF ANIMAL VIRUSES * : A REVIEW , 1965, Photochemistry and photobiology.

[34]  C. Crumpacker,et al.  Inactivation of Herpes Simplex Virus with Methylene Blue, Light and Electricity , 1979, Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine.

[35]  S. Menezes,et al.  Photodynamic action of methylene blue: repair and mutation in Escherichia coli. , 1990, Journal of photochemistry and photobiology. B, Biology.

[36]  L. Grossman,et al.  PHOTODYNAMIC DEGRADATION OF NUCLEIC ACIDS * , 1965, Photochemistry and photobiology.

[37]  Karl Weiss,et al.  The laser photolysis of methylene blue , 1967 .

[38]  J. Kelly,et al.  PHOTO‐INDUCED ELECTRON TRANSFER FROM NUCLEOTIDES TO RUTHENIUM‐TRIS‐1,4,5,8TETRAAZAPHENANTHRENE: MODEL FOR PHOTOSENSITIZED DNA OXIDATION , 1992, Photochemistry and photobiology.

[39]  U. Takahama,et al.  INHIBITION OF RESPIRATION AND LOSS OF MEMBRANE INTEGRITY BY SINGLET OXYGEN GENERATED BY A PHOTOSENSITIZED REACTION IN NEUROSPORA CRASSA CONIDIA , 1981 .

[40]  D. F. Bradley,et al.  Electric birefringence and dichroism of acridine orange and methylene blue complexes with polynucleotides , 1972, Biopolymers.

[41]  I. Kochevar,et al.  THE ROLE OF GROUND STATE COMPLEXATION IN THE ELECTRON TRANSFER QUENCHING OF METHYLENE BLUE FLUORESCENCE BY PURINE NUCLEOTIDES , 1991, Photochemistry and photobiology.

[42]  L. Lindqvist,et al.  LASER PHOTOLYSIS STUDY OF TRIPLET EOSIN AND THIONINE REACTIONS IN PHOTOSENSITIZED OXIDATIONS , 1974 .

[43]  H. Rosenkranz,et al.  A study of the photoinduced mutagenicity of methylene blue. , 1977, Mutation research.

[44]  G. Chihara,et al.  Biological photochemistry. I. The correlation between the photodynamical behaviors and the chemical structures of nucleic acid-bases, nucleosides, and related compounds in the presence of methylene-blue. , 1965, Chemical & pharmaceutical bulletin.

[45]  R. Floyd,et al.  Hydroxyl free radical adduct of deoxyguanosine: sensitive detection and mechanisms of formation. , 1986, Free radical research communications.

[46]  J. Joussot-Dubien,et al.  pH DEPENDENCE OF SINGLET OXYGEN PRODUCTION IN AQUEOUS SOLUTIONS USING THIAZINE DYES AS PHOTOSENSITIZERS , 1975, Photochemistry and photobiology.

[47]  G. Buettner,et al.  Hydrogen peroxide and hydroxyl radical formation by methylene blue in the presence of ascorbic acid , 1984, Radiation and environmental biophysics.

[48]  T. Köllner,et al.  Fluorescence formation during photodynamic therapy in the nucleus of cells incubated with cationic and anionic water-soluble photosensitizers. , 1992, Journal of photochemistry and photobiology. B, Biology.

[49]  N. Krinsky,et al.  A COMPARATIVE STUDY OF PHOTODYNAMIC OXIDATION AND RADIOFREQUENCY‐DISCHARGE‐GENERATED 1O2 OXIDATION OF GUANOSINE , 1973, Photochemistry and photobiology.

[50]  S. Jovanovic,et al.  One-electron redox potentials of purines and pyrimidines , 1986 .

[51]  G. Bennett,et al.  Targeted neuronal lesion induced by photosensitizing dyes , 1990, Brain Research.

[52]  L. Grossweiner,et al.  PHOTODYNAMIC DAMAGE TO EGG LECITHIN LIPOSOMES * , 1981 .

[53]  R. Austin,et al.  DNA motions in the nucleosome core particle. , 1982, Proceedings of the National Academy of Sciences of the United States of America.

[54]  R. Bonneau,et al.  MECHANISM OF PHOTOREDUCTION OF THIAZINE DYES BY EDTA STUDIED BY FLASH PHOTOLYSIS—III CONSEQUENCES OF A NEWLY FOUND pKT OF THIONINE ON THE MECHANISM IN BASIC SOLUTIONS , 1975 .

[55]  P. Kamat,et al.  Temperature dependence of quenching rates and efficiencies of net forward and reverse electron transfer in the quenching of protonated triplet methylene blue by complexes of iron(II) , 1982 .

[56]  D. Ewing,et al.  METHYLENE BLUE SENSITIZED PHOTOINACTIVATION OF E. COLI RIBOSOMES: EFFECT ON THE RNA AND PROTEIN COMPONENTS † , 1978, Photochemistry and photobiology.

[57]  J. V. van Lier,et al.  Photosensitized reactions of nucleic acids. , 1986, Biochimie.

[58]  A. Cincotta,et al.  NOVEL RED ABSORBING BENZO[a]PHENOXAZINIUM and BENZO[a]PHENOTHIAZINIUM PHOTOSENSITIZERS: in vitro EVALUATION , 1987, Photochemistry and photobiology.

[59]  Grossweiner Li Photochemical inactivation of enzymes. , 1976 .

[60]  P. Kamat,et al.  Kinetics of photobleaching recovery in the iron(II)-thionine system , 1981 .

[61]  R. H. Young,et al.  THE PHOTOREDUCTION OF METHYLENE BLUE BY AMINES—II. AN INVESTIGATION OF THE DECAY OF SEMIREDUCED METHYLENE BLUE , 1976 .

[62]  L. Grossweiner,et al.  HYDRODYNAMIC EFFECTS IN THE PHOTOSENSITIZED LYSIS OF LIPOSOMES * , 1982 .

[63]  R. Cunningham,et al.  Enzymatic recognition of DNA modifications induced by singlet oxygen and photosensitizers. , 1990, Nucleic acids research.

[64]  L. Goodman,et al.  The Pharmacological Basis of Therapeutics , 1941 .

[65]  H. Berg,et al.  Redox processes during photodynamic damage of DNA , 1980 .

[66]  B. Nordén,et al.  Structural transitions of chromatin at low salt concentrations: a flow linear dichroism study. , 1985, Biochemistry.

[67]  D. Valenzeno,et al.  PHOTOMODIFICATION OF BIOLOGICAL MEMBRANES WITH EMPHASIS ON SINGLET OXYGEN MECHANISMS , 1987, Photochemistry and photobiology.

[68]  D. Bagley,et al.  Selective surface staining of bladder tumors by intravesical methylene blue with enhanced endoscopic identification , 1984, Cancer.

[69]  A. Wacker,et al.  Mutagenic activity of thiopyronine and methylene blue in combination with visible light. , 1963, Biochemical and biophysical research communications.

[70]  H. Sies Biochemistry of oxidative stress , 1986 .

[71]  J. Kappler,et al.  Formation of an Adduct with Tris (hydroxymethyl) aminomethane during the Photooxidation of Deoxyribonucleic Acid and Guanine Derivatives , 1966 .

[72]  J. Litwin,et al.  The effect of photosensitizing dyes on the 3H-thymidine incorporation of cells grown in vitro. , 1973, Experimental cell research.

[73]  A. Knowles,et al.  A STUDY OF THE METHYLENE BLUE‐SENSITIZED OXIDATION OF AMINO ACIDS , 1972, Photochemistry and photobiology.

[74]  J. Piette,et al.  MECHANISMS FOR DYE‐MEDIATED PHOTODYNAMIC ACTION: SINGLET OXYGEN PRODUCTION, DEOXYGUANOSINE OXIDATION AND PHAGE INACTIVATING EFFICIENCIES , 1982, Photochemistry and photobiology.

[75]  B. Hayes,et al.  Ion-induced DNA structure change in nucleosomes. , 1986, Biochemistry.

[76]  C. Carre,et al.  A photochemical study of the methylene blue/acrylamide system in view of its use for holographic recording under red illumination , 1988 .

[77]  G. Oster,et al.  Dye-sensitized photoinactivation of tumor cells in vitro. , 1961, Cancer research.

[78]  B. Bhowmik,et al.  Photoinduced interaction of thionine with phospholipid and cholesterol in artificial membranes. , 1991, Journal of photochemistry and photobiology. B, Biology.

[79]  Y. Wakayama,et al.  PHOTOSENSITIZED INACTIVATION OF E. COLI CELLS IN TOLUIDINE BLUE‐LIGHT SYSTEM , 1980, Photochemistry and photobiology.

[80]  D. M. Brown,et al.  Base-specific reactions useful for DNA sequencing: methylene blue--sensitized photooxidation of guanine and osmium tetraoxide modification of thymine. , 1978, Nucleic acids research.

[81]  D. McConnell,et al.  LASER FLASH SPECTROSCOPY OF METHYLENE BLUE WITH NUCLEIC ACIDS , 1987, Photochemistry and photobiology.

[82]  L. Andrews,et al.  ANION AND SOLVENT EFFECTS ON THE RATE OF REDUCTION OF TRIPLET EXCITED THIAZINE DYES BY FERROUS IONS , 1977 .

[83]  Robert H. Austin,et al.  Evidence for kinks in DNA folding in the nucleosome , 1987, Nature.

[84]  L. Lutwick,et al.  Effects of photodynamic action on E. coli. , 1969, Archives of biochemistry and biophysics.

[85]  R. Straight,et al.  INACTIVATION AND MUTAGENESIS OF Herpes VIRUS BY PHOTODYNAMIC TREATMENT WITH THERAPEUTIC DYES , 1989, Photochemistry and photobiology.

[86]  S. Steenken,et al.  Pattern of OH radical reaction with adenine and its nucleosides and nucleotides. Characterization of two types of isomeric OH adduct and their unimolecular transformation reactions , 1990 .

[87]  I. Fridovich,et al.  The utility of superoxide dismutase in studying free radical reactions. II. The mechanism of the mediation of cytochrome c reduction by a variety of electron carriers. , 1970, The Journal of biological chemistry.

[88]  R. B. Misra,et al.  Evaluation of chemically-induced phototoxicity to aquatic organism using Paramecium as a model. , 1986, Biochemical and biophysical research communications.

[89]  L. Dubertret,et al.  PERMEATION OF LYSOSOMAL MEMBRANES IN THE COURSE OF PHOTOSENSITIZATION WITH METHYLENE BLUE AND HEMATOPORPHYRIN: STUDY BY CELLULAR MICROSPECTROFLUOROMETRY , 1983, Photochemistry and photobiology.

[90]  J. Cadet,et al.  COMPARATIVE STUDY OF OXIDATION OF NUCLEIC ACID COMPONENTS BY HYDROXYL RADICALS, SINGLET OXYGEN AND SUPEROXIDE ANION RADICALS , 1978, Photochemistry and photobiology.

[91]  L. Waskell,et al.  Studies on the photosensitized breakdown of guanosine by methylene blue. , 1966, Biochimica et biophysica acta.

[92]  E. Gajewski,et al.  Substrate specificity of the Escherichia coli Fpg protein (formamidopyrimidine-DNA glycosylase): excision of purine lesions in DNA produced by ionizing radiation or photosensitization. , 1992, Biochemistry.

[93]  H. Rosenkranz,et al.  Immunofluorescence for the detection of photochemical lesions in intracellular DNA. , 1976, Experimental cell research.

[94]  I. Fridovich,et al.  Intracellular production of superoxide radical and of hydrogen peroxide by redox active compounds. , 1979, Archives of biochemistry and biophysics.

[95]  R. Floyd,et al.  Methylene blue plus light mediates 8-hydroxyguanine formation in DNA. , 1989, Archives of biochemistry and biophysics.

[96]  R. Langlois,et al.  PHTHALOCYANINE AND NAPHTHALOCYANINE PHOTOSENSITIZED OXIDATION OF 2′‐DEOXYGUANOSINE: DISTINCT TYPE I AND TYPE II PRODUCTS , 1984 .

[97]  J. Joussot-Dubien,et al.  ÉTUDE EN SPECTROSCOPIE PAR ÉCLAIR DES COLORANTS THIAZINIQUES EN SOLUTION AQUEUSE , 1967 .

[98]  S. L. Fornili,et al.  Solvent isotope effect in the monomer–dimer equilibrium of methylene blue , 1981 .

[99]  J. Martín,et al.  Oxygen radicals are generated by dye-mediated intracellular photooxidations: a role for superoxide in photodynamic effects. , 1987, Archives of biochemistry and biophysics.

[100]  M. Rougée,et al.  SINGLET MOLECULAR OXYGEN QUENCHING BY SATURATED AND UNSATURATED FATTY‐ACIDS AND BY CHOLESTEROL , 1989, Photochemistry and photobiology.

[101]  R. Rees,et al.  THE PHOTOKILLING OF BLADDER CARCINOMA CELLS in vitro BY PHENOTHIAZINE DYES , 1990, Photochemistry and photobiology.

[102]  I. Saito,et al.  OCCURRENCE OF THE SINGLET‐OXYGEN MECHANISM IN PHOTODYNAMIC OXIDATIONS OF GUANOSINE * , 1975, Photochemistry and photobiology.

[103]  J. Bunting,et al.  A TEST OF THE SINGLET OXYGEN MECHANISM OF CATIONIC DYE PHOTOSENSITIZATION OF MITOCHONDRIAL DAMAGE , 1992, Photochemistry and photobiology.

[104]  B. Nordén,et al.  Structure of methylene blue–DNA complexes studied by linear and circular dichroism spectroscopy , 1982, Biopolymers.

[105]  R. Floyd,et al.  Mediation of 8-hydroxy-guanine formation in DNA by thiazin dyes plus light. , 1990, Free radical biology & medicine.

[106]  W. Gill,et al.  Inactivation of bladder tumor cells and enzymes by methylene blue plus light. , 1987, The Journal of urology.

[107]  J. Le Petit,et al.  REGENERATION OF NAD+ AND NADP+ COFACTORS BY PHOTOSENSITIZED ELECTRON TRANSFER , 1982 .

[108]  J. Sullivan,et al.  Effect of methylene blue on estrogen-receptor activity. , 1989, Radiology.

[109]  R. Austin,et al.  Dependence of oxygen quenching of intercalated methylene blue triplet lifetime on DNA base‐pair composition , 1986, Biopolymers.

[110]  T Ito,et al.  CELLULAR AND SUBCELLULAR MECHANISMS OF PHOTODYNAMIC ACTION: THE 1 O2 HYPOTHESIS AS A DRIVING FORCE IN RECENT RESEARCH , 1978, Photochemistry and photobiology.

[111]  U. Andley,et al.  Oxidative damage to human lens enzymes. , 1987, Current eye research.

[112]  R. Herrmann,et al.  Effect of Deoxyribonucleic Acid Ligands on Deoxyribonucleases and Deoxyribonucleic Acid Polymerase I of Escherichia coli K-12 , 1972, Journal of bacteriology.

[113]  J. Cadet,et al.  Photosensitized formation of 7,8-dihydro-8-oxo-2'-deoxyguanosine (8-hydroxy-2'-deoxyguanosine) in DNA by riboflavin: a nonsinglet oxygen-mediated reaction , 1992 .

[114]  R. Buxton,et al.  Dye sensitivity correlated with envelope protein changes in dye (sfrA) mutants of Escherichia coli K12 defective in the expression of the sex factor F. , 1983, Journal of general microbiology.

[115]  B. Nordén,et al.  Induced CD of DNA intercalators: Electric dipole allowed transitions , 1987, Biopolymers.

[116]  A. Girotti,et al.  PHOTODYNAMIC LIPID PEROXIDATION IN BIOLOGICAL SYSTEMS * , 1990, Photochemistry and photobiology.

[117]  Formation of superoxide ion via one-electron transfer from electron donors to singlet oxygen , 1983 .

[118]  J. Carew,et al.  PROBING PHOTODYNAMIC DAMAGE IN NUCLEIC ACIDS WITH A DAMAGE‐SPECIFIC DNA BINDING PROTEIN: A COMPARISON OF THE B and Z DNA CONFORMATIONS , 1983, Photochemistry and photobiology.

[119]  G. Grampp,et al.  Photoinduced Back Electron Transfer within Geminate Radical Ion Pairs. Observation of the Marcus Inverted Region in the System Thionine with Several Aromatic Donors , 1992 .

[120]  N. Krinsky,et al.  PROTECTIVE ACTION OF CAROTENOID PIGMENTS AGAINST PHOTODYNAMIC DAMAGE TO LIPOSOMES* , 1973, Photochemistry and photobiology.

[121]  C. Racinet,et al.  Pregnancy after oocyte collection and total ovariectomy. , 1989, The New England journal of medicine.

[122]  A. Knowles A MECHANISM FOR THE METHYLENE BLUE SENSITIZED OXIDATION OF NUCLEOTIDES , 1971, Photochemistry and photobiology.

[123]  J. Martín,et al.  The role of oxygen radicals in dye-mediated photodynamic effects in Escherichia coli B. , 1987, The Journal of biological chemistry.

[124]  G. S. Johnson,et al.  The effect of growth conditions on NAD+ and NADH concentrations and the NAD+:NADH ratio in normal and transformed fibroblasts. , 1974, The Journal of biological chemistry.

[125]  I. Saito,et al.  Mechanism of dye-sensitized photooxidation of tryptophan, tryptamine, and their derivatives. Singlet oxygen process in competition with type I process. , 1982 .

[126]  H. Kramer,et al.  Reactivity of Organic Dye Triplet States in Electron Transfer Processes , 1976 .

[127]  J. Piette,et al.  Biological consequences associated with DNA oxidation mediated by singlet oxygen. , 1991, Journal of photochemistry and photobiology. B, Biology.

[128]  G. Beddard,et al.  Photophysical Properties of Thionine and Methylene Blue When Bound to Dna, Polynucleotides or Nucleotides , 1992 .

[129]  H. Aiba,et al.  Photodynamic guanine modification by hematoporphyrin is specific for single-stranded DNA with singlet oxygen as a mediator. , 1986, The Journal of biological chemistry.

[130]  P. Merkel,et al.  UNAMBIGUOUS EVIDENCE FOR THE PARTICIPATION OF SINGLET OXYGEN ( 1 δ) IN PHOTODYNAMIC OXIDATION OF AMINO ACIDS , 1972, Photochemistry and photobiology.

[131]  H. Berg,et al.  352 - Redox processes during photodynamic damage of DNA III. Redox mechanism of photosensitization and radical reaction☆ , 1980 .

[132]  C. Babbs,et al.  Methylene blue as an inhibitor of superoxide generation by xanthine oxidase. A potential new drug for the attenuation of ischemia/reperfusion injury. , 1991, Biochemical pharmacology.

[133]  J. Kelly,et al.  LASER FLASH SPECTROSCOPY OF METHYLENE BLUE WITH NUCLEIC ACIDS. EFFECTS OF IONIC STRENGTH AND pH , 1989, Photochemistry and photobiology.

[134]  R. Austin,et al.  Molecular motion of DNA as measured by triplet anisotropy decay. , 1982, Proceedings of the National Academy of Sciences of the United States of America.

[135]  J. R. Perdrau,et al.  The Photodynamic Action of Methylene Blue on Certain Viruses , 1933 .

[136]  L. Oberley,et al.  Role of superoxide dismutase in cancer: a review. , 1979, Cancer research.

[137]  T. Ito,et al.  TOLUIDINE BLUE: THE MODE OF PHOTODYNAMIC ACTION IN YEAST CELLS , 1977, Photochemistry and photobiology.

[138]  G. Beddard,et al.  Picosecond study of the luminescence and transient absorption of methylene blue–polynucleotide complexes , 1990 .

[139]  H M Jensen,et al.  Lack of toxicity of methylene blue chloride to supravitally stained human mammary tissues. , 1983, Cancer research.

[140]  Takashi Ito THE DEPENDENCE OF PHOTOSENSITIZING EFFICACY OF ACRIDINE ORANGE AND TOLUIDINE BLUE ON THE DEGREE OF SENSITIZER‐CELL INTERACTION , 1980 .

[141]  S. Baron,et al.  Inactivation of viruses by the photodynamic action of toluidine blue. , 1960, Journal of immunology.

[142]  B. Epe Genotoxicity of singlet oxygen. , 1991, Chemico-biological interactions.

[143]  Barry Halliwell,et al.  DNA damage by oxygen‐derived species Its mechanism and measurement in mammalian systems , 1991, FEBS letters.

[144]  Z. Darżynkiewicz,et al.  Photosensitizing effects of the tricyclic heteroaromatic cationic dyes pyronin Y and toluidine blue O (tolonium chloride). , 1988, Cancer research.

[145]  R. Young,et al.  THE PHOTOREDUCTION OF METHYLENE BLUE BY AMINES—I. A FLASH PHOTOLYSIS STUDY OF THE REACTION BETWEEN TRIPLET METHYLENE BLUE AND AMINES , 1976 .

[146]  D. McConnell,et al.  Base-specific photocleavage of DNA induced by nanosecond U.V. pulsed laser radiation or methylene blue sensitisation , 1987 .

[147]  D. McConnell,et al.  Methylene blue photosensitised strand cleavage of DNA: effects of dye binding and oxygen. , 1987, Nucleic acids research.

[148]  N. Dattagupta,et al.  Interactions of heteroaromatic compounds with nucleic acids. 2. Influence of substituents on the base and sequence specificity of intercalating ligands. , 1975, European journal of biochemistry.

[149]  A. Savino,et al.  Photodynamic inactivation of E. coli by immobilized or coated dyes on insoluble supports , 1985 .

[150]  G. Oster,et al.  Photobleaching and Photorecovery of Dyes , 1954 .

[151]  I. Yamazaki,et al.  Microchannel‐plate photomultiplier applicability to the time‐correlated photon‐counting method , 1985 .

[152]  I. Mcfadyen The dangers of intra‐amniotic methylene blue , 1992, British journal of obstetrics and gynaecology.

[153]  J. Kanofsky,et al.  QUENCHING OF SINGLET OXYGEN BY BIOMOLECULES FROM L1210 LEUKEMIA CELLS , 1992, Photochemistry and photobiology.

[154]  OscarH Will III,et al.  PROTECTION OF Ustilago violacea FROM TOLUIDINE BLUE PHOTOSENSITIZATION and HYDROGEN PEROXIDE INDUCED KILLING and MITOTIC RECOMBINATION BY CAROTENES , 1988, Photochemistry and photobiology.

[155]  M. Egholm,et al.  Photolytic cleavage of DNA by nitrobenzamido ligands linked to 9-aminoacridines gives DNA polymerase substrates in a wavelength-dependent reaction. , 1991, Bioconjugate chemistry.

[156]  The growth-inhibitory effects of some dyes on different Mycoplasma and Acholeplasma spp. , 1985, Journal of general microbiology.

[157]  H. Horiuchi,et al.  Relaxation of supercoiled plasmid DNA by oxidative stresses in Escherichia coli , 1984, Journal of bacteriology.

[158]  B. Nordén,et al.  Ionic strength dependence of the binding of methylene blue to chromatin and calf thymus DNA. , 1992, Journal of biomolecular structure & dynamics.

[159]  G. Speit Intercalating substances do not induce sister-chromatid exchanges (SCEs) in vivo. , 1982, Mutation research.

[160]  J. Joussot-Dubien,et al.  pH DEPENDENCE OF SINGLET OXYGEN PRODUCTION IN AQUEOUS SOLUTIONS USING TOLUIDINE BLUE AS A PHOTOSENSITIZER , 1975, Photochemistry and photobiology.

[161]  H. Jacob PHOTO‐OXIDATION SENSITIZED BY METHYLENE BLUE, THIOPYRONINE, AND PYRONINE‐IV. THE BEHAVIOUR OF THIOPYRONINE IN SUSPENSIONS OF BACTERIA * , 1974 .

[162]  K. Loach Thin-layer chromatographic separation of methylene blue and related thiazine dyes , 1971 .

[163]  D. Macphee,et al.  Induction of base-pair substitution and frameshift mutations in wild-type and repair-deficient strains of Salmonella typhimurium by the photodynamic action of methylene blue. , 1975, Mutation research.

[164]  N. Krinsky,et al.  CAROTENOID CHROMOPHORE LENGTH AND PROTECTION AGAINST PHOTOSENSITIZATION , 1974, Photochemistry and photobiology.

[165]  M. Hamann,et al.  PHOTODYNAMIC ALTERATIONS OF THE CELL ENVELOPE OF PROTEUS MIRABILIS AND THEIR REPAIR , 1975, Photochemistry and photobiology.

[166]  Steen Steenken,et al.  Purine bases, nucleosides, and nucleotides: aqueous solution redox chemistry and transformation reactions of their radical cations and e- and OH adducts , 1989 .

[167]  S. Boiteux,et al.  Escherichia coli Fpg protein and UvrABC endonuclease repair DNA damage induced by methylene blue plus visible light in vivo and in vitro , 1991, Journal of bacteriology.

[168]  M. Simon,et al.  The photodynamic reaction of methylene blue with deoxyribonucleic acid. , 1962, Journal of molecular biology.

[169]  Takashi Ito,et al.  ENHANCING EFFECT OF ASCORBATE ON TOLUIDINE BLUE‐PHOTOSENSITIZATION OF YEAST CELLS , 1982 .

[170]  H. Jacob IN VIVO PRODUCTION OF DNA SINGLE‐STRAND BREAKS BY PHOTODYNAMIC ACTION , 1971, Photochemistry and photobiology.

[171]  S. Maiti,et al.  Visible light induced DNA-protein crosslinking in DNA-histone complex and sarcoma-180 chromatin in the presence of methylene blue. , 1990, Journal of photochemistry and photobiology. B, Biology.

[172]  J. Legrange,et al.  Dependence of DNA helix flexibility on base composition , 1983, Nature.

[173]  Michelinf M. Mathfws-Roth PHOTOSENSITIZATION IN SARCINA LUTE A: DIFFERENT MECHANISMS OF EXOGENOUS AND ENDOGENOUS PHOTOSENSITIZERS , 1977 .

[174]  R. Langlois,et al.  PHTHALOCYANINE AND NAPHTHALOCYANINE PHOTOSENSITIZED OXIDATION OF 2′‐DEOXYGUANOSINE , 1992 .