EPR and Spectrophotometric Studies of Free Radicals (O2·-, ·OH, BPD-MA·-) and Singlet Oxygen (1O2) Generated by Irradiation of Benzoporphyrin Derivative Monoacid Ring A

Photochemistry and Photobiology

Volumn 65, Issue 5, 1997, Pages 818-827

  Hadjur, Christophe ^a   Wagnières, Georges ^a   Monnier, Philippe ^b   Van Den Bergh, Hubert ^a  

^a EPFL   (Switzerland)

^b LAUSANNE UNIVERSITY HOSPITAL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030995720     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1997.tb01929.x     Document Type: Article

References (50)

1. Richter, A. M., B. Kelly, J. Chow, D. J. Liu, G. H. N. Towers, D. Dolphin and J. G. Levy (1987) Preliminary studies on a more effective phototoxic agent than hematoporphyrin. J. Natl. Cancer Inst. 79, 1327-1332.
2. Richter, A. M., E. D. Sternberg, E. Waterfield, D. Dolphin and J. G. Levy (1988) Characterization of benzoporphyrin derivative, a new photosensitizer. SPIE 997, 132-138.
3. Richter, A. M., E. Waterfield, A. K. Jain, E. D. Sternberg, D. Dolphin and J. G. Levy (1990) In vitro evaluation of phototoxic properties of four structurally related benzoporphyrin derivatives. Photochem. Photobiol. 52, 495-500.
4. Lui, H. and R. R. Anderson (1993) Photodynamic therapy in dermatology: recent developments. Dermatol. Clinics 11, 1-13.
5. Levy, J. G., A. Chan and H. A. Strong (1995) The clinical status of benzoporphyrin derivative. SPIE 2625, 86-95.
6. Miller, J. W. and D. Husain (1996) Photodynamic therapy of choroidal neovascularization using liposomal benzoporphyrin derivative. Lasers Surg. Med. Suppl. 8, 29.
7. Jamieson, C. H. M., W. N. McDonald and J. G. Levy (1990) Differential uptake of benzoporphyrin derivative by leukemic versus normal cells. Leuk. Res. 14, 209-219.
8. Jamieson, C. H. M., A. Hornby, A. M. Richter, D. Mitchell and J. G. Levy (1993) Relative sensitivity of leukemic (CML) and normal progenitor cells to treatment with the photosensitizer benzoporphyrin derivative and light. J. Hematother. 2, 383-386.
9. North, J., H. Neyndorff and J. G. Levy (1993) Photosensitizers as virucidal agents. J. Photochem. Photobiol. B Biol. 17, 99-108.
10. North, J., H. Neyndorff, D. King and J. G. Levy (1992) Viral inactivation in blood and red cell concentrates with benzoporphyrin derivative. Blood Cells 18, 129-140.
11. North, J., R. Coombs and J. G. Levy (1992) Photoinactivation of HIV by benzoporphyrin derivative. In Photodynamic Therapy and Biochemical Lasers (Edited by P. Spinelli, M. Dal Fante and R. Marchesini), pp. 103-110. Elsevier Science, Amsterdam.
12. Curry, P. M. and J. G. Levy (1993) Stress protein expression in murine tumor cells following photodynamic therapy with benzoporphyrin derivative. Photochem. Photobiol. 58, 374-379.
13. Obochi, M. O. K., A. J. Canaan, A. K. Jain, A. M. Richter and J. G. Levy (1995) Targeting activated lymphocytes with photodynamic therapy: susceptibility of mitogen-stimulated splenic lymphocytes to benzoporphyrin derivative (BPD) photosensitization. Photochem. Photobiol. 62, 169-175.
14. Richter, A. M., S. Yip, E. Waterfield, P. M. Logan, C. E. Slonecker and J. G. Levy (1991) Mouse photosensitization with benzoporphyrin derivatives and Photofrin®: macroscopic and microscopic evaluation. Photochem. Photobiol. 53, 281-286.
15. Aveline, B., T. Hasan and R. W. Redmond (1994) Photophysical and photosensitizing properties of benzoporphyrin derivative monoacid ring A (BPD-MA). Photochem. Photobiol. 59, 328-335.
16. Aveline, B., T. Hasan and R. W. Redmond (1995) The effects of aggregation, protein binding and cellular incorporation on the photophysical properties of benzoporphyrin derivative monoacid ring A (BPD-MA). J. Photochem. Photobiol. B Biol. 30, 161-169.
17. Allison, A., E. Waterfield, A. M. Richter and J. G. Levy (1991) The effects of plasma lipoproteins on in vitro tumor cell killing and in vivo tumor photosensitization with benzoporphyrin derivative. Photochem. Photobiol. 54, 709-715.
18. Allison, A., Prichard, P., A. M. Richter and J. G. Levy (1990) The plasma distribution of benzoporphyrin derivative and the effects of plasma lipoproteins on its distribution. Photochem. Photobiol. 2, 501-507.
19. Buettner, G. R. and L. W. Oberley (1978) Considerations in the spin-trapping of superoxide and hydroxyl radical in aqueous systems using DMPO. Biochem. Biophys. Res. Commun. 83, 69-74.
20. Batzri, S. and E. D. Korn (1980) Single bilayer liposomes prepared without sonication. Biochim. Biophys. Acta 594, 53-84.
21. Strul, G., A. A. Frimer and L. Weiner (1993) Spin trapping of free radical penetration into liposomal membranes. J. Chem. Soc. Perkin Trans. 2, 2057-2059.
22. Hadjur, C., A. Jeunet and P. Jardon (1994) Photosensitization by hypericin: ESR evidence for singlet oxygen and superoxide anion radicals formation in an in vitro model. J. Photochem. Photobiol. B Biol. 26, 67-74.
23. Fridovich, I. (1985) Cytochrome c. In CRC Handbook of Methods for Oxygen Radical Research (Edited by R. A. Greenwald), pp. 121-122. CRC Press, Boca Raton, FL.
24. Fridovich, I. (1970) Quantitative aspects of the production of superoxide anion radical by milk xanthine oxidase. J. Biol. Chem. 245, 4053-4057.
25. Beyer, W. F. and I. Fridovich (1962) Phosphate, not superoxide dismutase, facilitates electron transfer from ferrous salts to cytochrome c. Arch. Biochem. Biophys. 58, 593-595.
26. Hadjur, C. and P. Jardon (1995) Quantitative analysis of superoxide radical anion radicals photosensitized by hypericin in a model membrane using the cytochrome c reduction method. J. Photochem. Photobiol. B Biol. 29, 147-156.
27. - and ·OH by irradiation of the photosensitizer zinc(II) phthalocyanine. J. Photochem. Photobiol. B Biol. (In press)
28. Hadjur, C. and A. Jeunet (1995) EPR evidence of superoxide anion radicals by irradiation of a PDT photosensitizer: hypericin. In Methods in Molecular Biology (Edited by A. Favier, B. Kalyanaraman, J. Cadet, M. Fontecave and J. L. Pierre), pp. 119-126. Birkhaüser Verlag, Basel.
29. -) and hydroxyl radicals (·OH) by irradiation of a new photodynamic therapy photosensitizer, Victoria blue BO. J. Photochem. Photobiol. B Biol. 32, 49-58.
30. - by benzoquinone in cyanoaromatic-sensitized photooxygenations. Tetrahedron Lett. 25, 2523-2526.
31. Lissi, E. A., M. V. Encinas, E. Lemp and M. A. Rubio (1993) Singlet oxygen bimolecular processes. Solvent and compartmentalization effects. Chem. Rev. 93, 699-723.
32. Rosen, G. M., E. Finkelstein and E. J. Rauckman (1982) A method for the detection of superoxide in biological systems. Arch. Biochem. Biophys. 215, 367-378.
33. Butler, J., G. G. Jayson and A. J. Swallow (1975) The reaction between the superoxide anion radical and cytochrome c. Biochim. Biophys. Acta 408, 215-222.
34. Spikes, J. D. (1989) Photosensitization. In The Science of Photobiology (Edited by K. C. Smith), pp. 79-100. Plenum Press, New York.
35. Finkelstein, E., G. M. Rosen and E. J. Rauckman (1980) Spin trapping of superoxide and hydroxyl radical: practical aspects. Arch. Biochem. Biophys. 200, 1-16.
36. Halliwell, B. and J. M. C. Gutteridge (1986) Oxygen free radicals and iron in relation to biology and medicine some problems and concepts. Arch. Biochem. Biophys. 246, 501-514.
37. Pou, S., D. J. Hassett, B. E. Britigan, M. S. Cohen and G. M. Rosen (1989) Problems associated with spin trapping oxygen-centered free radicals in biological systems. Anal. Biochem. 177, 1-6.
38. Feix, J. B. and B. Kalyanaraman (1991) Production of singlet oxygen-derived hydroxyl radical adducts during merocyanine-540-mediated photosensitization: analysis by ESR-spin trapping and HPLC with electrochemical detection. Arch. Biochem. Biophys. 291, 43-51.
39. Moan, J. (1980) A new method to detect porphyrin radicals in aqueous solutions. Acta Chem. Scand. B 34, 519-521.
40. Lion, Y., M. Delmelle and A. Van De Vorst (1976) New method of detecting singlet oxygen production. Nature 263, 442-443.
41. Darmanyan, A., L. Burel, D. Eloy and P. Jardon (1994) Singlet oxygen production by hypericin in various solvents. J. Chim. Phys. 91, 1774-1785.
42. Senthil, V., L. R. Jones, K. Senthil and L. I. Grossweiner (1994) Hypericin photosensitization in aqueous model systems. Photochem. Photobiol. 59, 40-47.
43. Henderson, B. W. and T. J. Dougerty (1992) How does photodynamic therapy work? Photochem. Photobiol. 1, 145-157.
44. Cauzzo, G., G. Gennari, G. Jori and J. D. Spikes (1977) The effect of chemical structure on the photosensitizing efficiencies of porphyrins. Photochem. Photobiol. 25, 389-395.
45. Sarna, T., J. Zajac, M. K. Bowman and T. G. Truscott (1991) Photoinduced electron transfer reactions of rose bengal and selected electron donors. J. Photochem. Photobiol. A Chem. 60, 295-310.
46. Weiner, L. and Y. Mazur (1992) EPR studies of hypericin. Photogeneration of free radicals and superoxide. J. Chem. Soc. Perkin Trans. 2, 1439-1442.
47. Buettner, G. R. and R. D. Hall (1987) Superoxide, hydrogen peroxide and singlet oxygen in hematoporphyrin derivative-cysteine, -NADH and light systems. Biochim. Biophys. Acta 923, 501-507.
48. Valduga, G., S. Nonell, E. Reddi, G. Jori and S. E. Braslavsky (1988) The production of singlet molecular oxygen by zinc(II) phthalocyanine in ethanol and in unilamellar vesicles. Chemicals quenching and phosphorescence studies. Photochem. Photobiol. 48, 1-5.
49. Valenzeno, D. P. (1987) Photomodification of biological membranes with emphasis on singlet oxygen mechanisms. Photochem. Photobiol. 46, 147-160.
50. Halliwell, B. and J. M. C. Gutteridge (1989) Free Radicals in Biology and Medicine, pp. 86-87. Clarendon Press, Oxford.