Role of Oxygen in the Phototoxicity of Phthalocyanines

References

• Altman S.A., Zastawny T.H., Randers L., Lin Z., Lumpkin J.A., Remacle J., Dizdaroglu M., Rao G. tert-Butylhydroperoxide-mediated DNA base damage in cultured mammalian cells. Mutation Research 1994; 306: 35–44
   PubMed Web of Science ®Google Scholar
• Agarwal R., Athar M., Bickers D.R., Mukhtar H. Evidence for the involvement of singlet oxygen in the photodestruction by chloroaluminium phthalocyanine tetrasulfonate. Biochemical and Biophysical Research Communications 1990; 173: 34–41
   PubMedGoogle Scholar
• Agarwal R., Athar M., Urban S.A., Bickers D.R., Mukhtar H. Involvement of singlet oxygen in chloroaluminum phthalocyanine tetrasulfonate-mediated photoenhancement of lipid peroxidation in rat epidermal microsomes. Cancer Letters 1991; 56: 125–129
   PubMedGoogle Scholar
• Agarwal R., Zaidi S.I.A., Athar M., Bickers D.R., Mukhtar H. Photodynamic effects of chloroaluminium phthalocyanine tetrasulfonate are mediated by singlet oxygen: in vivo and in vitro studies utilizing hepatic microsomes as a model membrane source. Archives of Biochemistry and Biophysics 1992; 294: 30–37
   PubMedGoogle Scholar
• Bachowski G.J., Ben Hur E., Girotti A.W. Phthalocyanine-sensitized lipid peroxidation in cell membranes: use of cholestrol and azide as probes of primary photochemistry. Journal of Photochemistry and Photobiology B—Biology 1991; 9: 307–321
   PubMed Web of Science ®Google Scholar
• Beeby A., Parker A.W., Simpson M.S.C., Phillips D. The effect of solvent deuteration on the photophysics of sulphonated aluminium phthalocyanine. Journal of Photochemistry and Photobiology B—Biology 1992; 16: 73–81
   Google Scholar
• Ben-Hur E. Basic photobiology and mechanisms of action of phthalocyanines. Photodynamic Therapy: Basic Principles and Clinical Application, B.W. Henderson, T.J. Dougherty. Marcel Dekker, New York 1992; 63–77, In
   Google Scholar
• Ben-Hur E., Carmichael A., Riesz P., Rosenthal I. Photochemical generation of superoxide radical and the cytotoxicity of phthalocyanines. International Journal of Radiation Biology 1985; 48: 837–846
   Web of Science ®Google Scholar
• Ben-Hur E., Margolis-Nunno H., Rywkin S., Horowitz B. The use of quenchers for enhanced specificity of photosensitized virus sterilization of blood. Prevention of Transfusion—Related Infections, F. Sieber, Boca Raton 1994, In (in press)
   Google Scholar
• Ben-Hur E., Rosenthal I. Factors affecting the photokilling of cultured Chinese hamster cells by phthalocyanines. Radiation Research 1985; 103: 403–409
   PubMedGoogle Scholar
• Ben-Hur E., Rosenthal I. Effect of antioxidants on phthalocyanine photosensitization of human erythrocytes. Optical Methods for Tumor Treatment and Detection: Mechanisms and Techniques in Photodynamic Therapy II, T.J. Dougherty. Society of Photo-Optical Instrumentation Engineers, Bellingham, Washington 1993; 1881: 334–342, In SPIE Proceedings
   Google Scholar
• Ben-Hur E., Rosenthal I., Granot(Graziani) Y. Inhibition of phthalocyanine-sensitized photohaemolysis of human erythrocytes by quercetin. Photochemistry and Photobiology 1993; 57: 984–988
   PubMedGoogle Scholar
• Brasseur N., Ali H., Autenrieth D., Langlois R., van Lier J.E. Biological activities of phthalocyanines III. Photoinactivation of V-79 Chinese hamster cells by tetrasulfophthalocyanines. Photochemistry and Photobiology 1985; 42: 515–521
   PubMedGoogle Scholar
• Chen J.Y., Rong X, Chen S.M., Lu F.D., Chen K.T., Cai H.X. Studies on the photochemical and photocytotoxic properties of the new PDT photosensitizer aluminium sulfonated phthalocyanine. Cancer Biochemistry and Biophysics 1991; 12: 103–116
   PubMedGoogle Scholar
• Daraio M.E., Aramendia P.F., San Roman E.A., Braslavsky S.E. Carboxylated zinc-phthalocyanines II. Dimerization and singlet molecular oxygen sensitization in hexadecyltrimethylammonium bromide micelles. Photochemistry and Photobiology 1991; 54: 367–374
   PubMedGoogle Scholar
• Davila J., Harriman A. Photosensitized oxidation of biomaterials and related model compounds. Photochemistry and Photobiology 1989; 50: 29–35
   PubMedGoogle Scholar
• Davila J., Harriman A. Photoreactions of macrocyclic dyes bound to human serum albumin. Photochemistry and Photobiology 1990; 51: 9–19
   PubMedGoogle Scholar
• Fingar V.H., Wieman T.J., Karavolos P.S., Doak K.W., Ouellet R., van Lier J.E. The effects of photodynamic therapy using differently substituted zinc phthalocyanines on vessel constriction, vessel leakage and tumour response. Photochemistry and Photobiology 1993; 58: 251–258
   PubMedGoogle Scholar
• Firey P.A., Jones T.W., Jori G., Rodgers M.A.J. Photoexcitation of zinc phthalocyanine in mouse myeloma cells: the observation of triplet states but not of singlet oxygen. Photochemistry and photobiology 1988; 48: 357–360
   PubMed Web of Science ®Google Scholar
• Foote C.S. Detection of singlet oxygen in complex systems: a critique. Biochemical and Clinical Aspects of Oxygen, S. Gutteridge, H.S. Mason. Academic, New York 1979; 603–626, In
   Google Scholar
• Fowler G.J.S., Devonshire R. Photobleaching of 1,3-diphenylisobenzofuran by novel phthalocyanine dye derivatives. Journal of Photochemistry and Photobiology B—Biology 1992; 14: 177–185
   PubMedGoogle Scholar
• Gantchev T.G. Spin-trapping of free radicals during phthalocyanine photosensitization of lymphoma cells in vitro. Cancer Biochemistry and Biophysics 1992; 13: 103–111
   PubMedGoogle Scholar
• Gantchev T.G., Uromov I.J., Hunting D.J., van Lier J.E. Photocytotoxicity and intracellular generation of free radicals by tetrasulphonated Al- and Zn-phthalocyanines. International Journal of Radiation Biology 1994; 65: 289–298
   PubMed Web of Science ®Google Scholar
• Gross E., Ehrenberg B., Johnson F.M. Singlet oxygen generation by porphyrins and the kinetics of 9,10-dimethylanthracene photosensitization in liposomes. Photochemistry and Photobiology 1993; 57: 808–813
   PubMed Web of Science ®Google Scholar
• Kim H., Rosenthal I., Kirschenbaum L., Riesz P. Photosensitized formation of ascorbate radicals by chloroaluminium phthalocyanine tetrasulfonate: an ESR study. Free Radicals in Biology and Medicine 1992; 13: 231–238
   PubMed Web of Science ®Google Scholar
• Kimel S., Tromberg B.J., Roberts W.G., Berns M.W. Singlet oxygen generation of porphyrins, chlorins, and phthalocyanines. Photochemistry and Photobiology 1989; 50: 175–183
   PubMedGoogle Scholar
• Korytowski W., Bachowski G.J., Girotti A.W. Photoperoxidation of cholestrol in homogenous solution, isolated membranes, and cells: comparison of the 5α- and 6β-hydroperoxides as indicators of singlet oxygen intermediacy. Photochemistry and Photobiology 1992; 56: 1–8
   PubMed Web of Science ®Google Scholar
• Krasnovsky A.A., Jr., Rodgers M.A.J., Galpern M.G., Rihter B., Kenney M.E., Lukjanetz E.A. Quenching of singlet molecular oxygen by phthalocyanines and naphthalocyanines. Photochemistry and Photobiology 1992; 55: 691–696
   PubMedGoogle Scholar
• Langlois R., Ali H., Brasseur N., Wagner J.R., van Lier J.E. Biological activities of phthalocyanines. IV. Type II sensitized photoxidation of l-tryptophan and cholesterol by sulfonated metallo phthalocyanines. Photochemistry and Photobiology 1986; 44: 117–123
   PubMed Web of Science ®Google Scholar
• Obochi M.O.K., Boyle R.W., Watts S.D., van Lier J.E. Photosensitization pathways of some zinc phthalocyanine (ZnPc) derivatives used in PDT. Photochemistry and Photobiology 1993; 57: 12S–12S, (Suppl.)
   Google Scholar
• Penning L.C., Rasch M., Ben Hur E., Dubbelman T.M.A.R., Havelaar A.C., van derZee J., Van Steveninck J. A role for the transient increase of cytoplasmic free calcium in cell rescue after photodynamic treatment. Biochimica et Biophysica Acta 1992; 1107: 255–260
   PubMedGoogle Scholar
• Ravanat J.L., Berger M., Benard F., Langlois R., Ouellet R., van Lier J.E., Cadet J. Phthalocyanine and naphthalocyanine photosensitized oxidation of 2′-deoxyguanosine: distinct type I and type II products. Photochemistry and Photobiology 1992; 55: 809–814
   Web of Science ®Google Scholar
• Rihter B.D., Bohorquez M.D., Rodgers M.A.J., Kenney M.E. Two new sterically hindered phthalocyanines: synthetic and photodynamic aspects. Photochemistry and Photobiology 1992; 55: 677–680
   PubMedGoogle Scholar
• Rodgers M.A.J. Reflections on type I photodynamic damage. Journal of Photochemistry and Photobiology B—Biology 1993; 18: 296–298
   PubMedGoogle Scholar
• Rosenthal I. Phthalocyanines as photodynamic sensitizers. Photochemistry and Photobiology 1991; 53: 859–870
   PubMed Web of Science ®Google Scholar
• Rosenthal I., Ben-Hur E. Ascorbate-assisted, phthalocyanine-sensitized photohaemolysis of human erythrocytes. International Journal of Radiation Biology 1992; 62: 481–486
   PubMed Web of Science ®Google Scholar
• Rosenthal I., Murali Krishna C., Riesz P., Ben-Hur E. The role of molecular oxygen in the photodynamic effect of phthalocyanines. Radiation Research 1986; 107: 136–142
   PubMed Web of Science ®Google Scholar
• Rosenthal I., Shafirovich V.Y., Geacintov N.E., Ben-Hur E., Horowitz B. The photochemical properties of fluoroaluminium phthalocyanine. Photochemistry and Photobiology 1994; 60: 215–220
   PubMedGoogle Scholar
• Rywkin S., Lenny L., Goldstein J., Geacintov N.E., Margolis-Nunno H., Horowitz B. Importance of type I and type II mechanisms in the photodynamic inactivation of viruses in blood with aluminium phthalocyanine derivatives. Photochemistry and Photobiology 1992; 56: 463–470
   PubMed Web of Science ®Google Scholar
• Shopova M., Gantchev T. Comparison of the photosensitizing efficiencies of haematoporphyrin and its derivative with that of free-base tetrasulphophthalocyanine in homogeneous and microheterogeneous media. Journal of Photochemistry and Photobiology B—Biology 1990; 6: 49–59
   PubMed Web of Science ®Google Scholar
• Teuchner K., Pfarrherr A., Stiel H., Freyer W., Leupold D. Spectroscopic properties of potential sensitizers for new photodynamic start mechanisms via two-step excited electronic states. Photochemistry and Photobiology 1993; 57: 465–471
   PubMedGoogle Scholar
• Wagner J.R., Ali H., Langlois R., Brasseur N., van Lier J.E. Biological activities of phthalocyanines. VI. Photooxidation of l-tryptophan by selectively sulfonated gallium phthalocyanines: singlet oxygen yields and efect of aggregation. Photochemistry and Photobiology 1987; 45: 587–594
   PubMedGoogle Scholar
• Zaidi S.I.A., Agarwal R., Eichler G., Rihter B.D., Kenney M.E., Mukhtar H. Photodynamic effects of new silicon phthalocyanines: in vitro studies utilizing rate hepatic microsomes and human erythrocyte ghosts as model membrane sources. Photochemistry and Photobiology 1993; 58: 204–210
   PubMed Web of Science ®Google Scholar
• Zhang X.F., Xu H.J., Chen D.W. substituted phthalo cyanine-sensitized photochemical generation of superoxide anion radical. Journal of Photochemistry and Photobiology B—Biology 1994; 22: 235–239
   PubMedGoogle Scholar