Kinetics and Yield of Singlet Oxygen Photosensitized by Hypericin in Organic and Biological Media

Photochemistry and Photobiology

Volumn 68, Issue 2, 1998, Pages 135-140

  Ehrenberg, Benjamin ^a,b   Anderson, Jamey L ^a   Foote, Christopher S ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b BAR ILAN UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

MUS;

DRUG DERIVATIVE; HYPERICIN; LIPOSOME; OXYGEN; PERYLENE; PHOTOSENSITIZING AGENT; SINGLET OXYGEN;

ARTICLE; CHEMISTRY; IN VITRO STUDY; KINETICS; PH; PHOTOCHEMISTRY; RADIATION EXPOSURE; SOLUTION AND SOLUBILITY; SPECTROPHOTOMETRY;

HYDROGEN-ION CONCENTRATION; KINETICS; LIPOSOMES; OXYGEN; PERYLENE; PHOTOCHEMISTRY; PHOTOSENSITIZING AGENTS; SINGLET OXYGEN; SOLUTIONS; SPECTROPHOTOMETRY;

EID: 0032134666     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1998.tb02479.x     Document Type: Article

References (49)

1. Brockman, H., M. N. Haschad, K. Maier and F. Pohl (1939) Hypericin, the photodynamically active pigment from Hypericum perforatum. Naturwissenschaften 27, 550-555.
2. Giese, A. C. (1980) Hypericism. Photochem. Photobiol. Rev. 5, 229-255.
3. Blum, H. F. (1941) Photodynamic Action and Diseases Caused by Light. Reinhold Publishing, New York.
4. Kraml, L. and W. Marwan (1983) Photomovement responses of the heterotrichous ciliate Blepharisma japonicum. Photochem. Photobiol. 37, 313-319.
5. Knox, J. P. and A. D. Dodge (1985) Isolation and activity of the photodynamic pigment hypericin. Plant Cell Environ. 8, 19-25.
6. Duran, N. and P. S. Song (1986) Hypericin and its photodynamic action. Photochem. Photobiol. 43, 677-680.
7. Meruelo, D., G. Lavie and D. Lavie (1988) Therapeutic agents with dramatic antiviral activity and little toxicity at effective doses: aromatic polycyclic diones hypericin and pseudohypericin. Proc. Natl. Acad. Sci. USA 85, 5230-5234.
8. Lavie, G., F. Valentine, B. Levin, Y. Mazur, G. Gallo, D. Lavie, L. Weiner and D. Meruelo (1989) Studies on the mechanisms of action of the antiretroviral agents hypericin and pseudohypericin. Proc. Natl. Acad. Sci. USA 86, 5963-5967.
9. Tang, J., J. M. Colacino, S. H. Larsen and W. Spitzer (1990) Virucidal activity of hypericin against enveloped and non-enveloped DNA and RNA viruses. Antiviral Res. 13, 313-326.
10. Carpenter, S. and G. A. Kraus (1991) Photosensitization is required for inactivation of equine infectious anemia virus by hypericin. Photochem Photobiol. 53, 169-174.
11. Diwu, Z. and J. W. Lown (1990) Phototherapeutic potential of alternative photosensitizers to porphyrins. Pharmacol. Ther. 63, 1-35.
12. Diwu, Z. (1995) Novel therapeutic and diagnostic applications of hypocrellins and hypericins. Photochem. Photobiol. 61, 529-539.
13. Dunn, R. C., J. L. Anderson, C. S. Foote and J. D. Simon (1993) Solution photochemistry of chlorine dioxide-mechanisms for the generation of atomic chlorine. J. Am. Chem. Soc. 115, 5307-5308.
14. Bashford, C. L. and J. C. Smith (1979) The determination of oxonol-membrane binding parameters by spectroscopic methods. Biophys. J. 25, 81-85.
15. Ehrenberg, B. (1992) Assessment of the partitioning of probes to membranes by spectroscopic titration. J. Photochem. Photobiol. B Biol. 14, 383-386.
16. Gross, E. and B. Ehrenberg (1989) The partition and distribution of porphyrins in liposomal membranes. A spectroscopic study. Biochim. Biophys. Acta 983, 118-122.
17. Ehrenberg, B. and E. Pevzner (1993) Spectroscopic properties of the potentiometric probe merocyanine-540 in solutions and in liposomes. Photochem. Photobiol. 57, 228-234.
18. Blum, A. and L. I. Grossweiner (1985) Singlet oxygen generation by HP1X, UPI and Hpd at 546 nm in phosphate buffer and in the presence of egg phosphatidylcholine liposomes. Photochem. Photobiol. 41, 27-32.
19. Fernandez, J. M., M. D. Bilgin and L. I. Grossweiner (1997) Singlet oxygen generation by photodynamic agents. J. Photochem. Photobiol. B Biol. 37, 131-140.
20. Moan, J. (1990) On the diffusion length of singlet oxygen in cells and tissue. J. Photochem. Photobiol. B Biol. 6, 343-344.
21. Wilkinson, F. and J. Brummer (1981) Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. J. Phys. Chem. Ref. Data 10, 809-999.
22. 2, Vol I (Edited by A. A. Frimer), pp. 177-224. CRC Press, Boca Raton, FL.
23. Rand, R. P. and A. V. Parsegian (1992) The forces between interacting bilayer membranes and the hydration of phospholipid assemblies. In The Structure of Biological Membranes (Edited by P. Yeagle), pp. 251-306. CRC Press, Boca Raton, FL.
24. Jenny, T. A. and Turro, N. J. (1982) Solvent deuterium isotope effects on the lifetime of singlet oxygen determined by direct emission spectroscopy at 1.27 μm. Tetrahedron Lett. 23, 2923-2926.
25. Hall, R. D. and C. F. Chignell (1987) Steady state near IR detection of singlet molecular oxygen: a Stern-Volmer quenching experiment with sodium azide. Photochem. Photobiol. 45, 459-464.
26. Lindig, B. A. and M. A. J. Rodgers (1981) Rate parameters for the quenching of singlet oxygen by water-soluble and lipid-soluble substrates in aqueous and micellar systems. Photochem. Photobiol. 33, 627-634.
27. Shimizu-Takahama, M., T. Egashira and U. Takahama (1981) Inhibition of respiration and loss of membrane integrity by singlet oxygen generated by a photosensitized reaction in Neurospora crassa conidia. Photochem. Photobiol. 33, 689-694.
28. Pooler, J. P. and D. P. Valenzeno (1979) The role of singlet oxygen in photooxidation of excitable cell membranes. Photochem. Photobiol. 30, 581-584.
29. Kobayashi, K. (1978) Effect of sodium azide on photodynamic induction of genetic changes in yeast. Photochem. Photobiol. 28, 535-538.
30. Bachowski, G. J., E. Ben-Hur and A. W. Girotti (1991) Phthalocyanine-sensitized lipid peroxidation in cell membranes: use of cholesterol and azide as probes of primary photochemistry. J. Photochem. Photobiol. B Biol. 9, 307-321.
31. g) photo-oxidation reactions in egg-yolk lecithin vesicles. J. Chem. Soc. Faraday Trans. I 82, 1627-1635.
32. Hoebeke, M., J. Piette and A. van de Vorst (1991) Photosensitized production of singlet oxygen by merocyanine 540 bound to liposomes. J. Photochem. Photobiol. B Biol. 9, 281-294.
33. Rodgers, M. A. J. (1988) On the problem involved in detecting luminescence from singlet oxygen in biological specimens. J. Photochem. Photobiol. B Biol. 1, 371-373.
34. Patterson, M. S., S. J. Madsen and B. C. Wilson (1990) Experimental tests of the feasibility of singlet oxygen luminescence monitoring in vivo during photodynamic therapy. J. Photochem. Photobiol. B Biol. 5, 69-84.
35. Baker, A. and J. R. Kanofsky (1991) Direct observation of singlet oxygen phosphorescence at 1270 nm from L1210 leukemia cells exposed to polyporphyrin and light. Arch Biochem. Biophys. 286, 70-75.
36. Baker, A. and J. R. Kanofsky (1993) Time-resolved studies of singlet-oxygen emission from L1210 leukemia cells labeled with 5-(N-hexadecanoyl)amino eosin - a comparison with a one-dimensional model of singlet-oxygen diffusion and quenching. Photochem. Photobiol. 57, 720-727.
37. Fu, Y. and J. R. Kanofsky (1995) Singlet oxygen generation from liposomes: a comparison of time-resolved 1270 nm emission with singlet oxygen kinetics calculated from a one dimensional model of singlet-oxygen diffusion and quenching. Photochem Photobiol. 62, 692-702.
38. g) bimolecular processes. Solvent and compartmentalization effects. Chem. Rev. 93, 699-723.
39. Fischkoff, S. and J. M. Vanderkooi (1975) Oxygen diffusion in biological and artificial membranes determined by the fluorochrome pyrene. J. Gen. Physiol. 65, 663-676.
40. g) J. Am. Chem. Soc. 105, 3423-3430.
41. Bouirig, H., D. Eloy and P. Jardon (1992) Formation et réactivité de l'oxygène singulet photosensibilisé par l'hypéricine dans des liposomes de dipalmitoylphosphatidylcholine. Mise en évidence d'une photooxydation retardée. J. Chim. Phys. 89, 1391-1411.
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. Jardon, P., N. Lazortchak and R. Gautron (1987) Formation d'oxygène singulet photosensibilisée par l'hypericine. Caractérisation et étude du mécanisme par spectroscopie laser. J. Chim. Phys. Phys. Chim. Biol. 84, 1141-1145.
44. Racinet, H., P. Jardon and R. Gautron (1988) Generation of singlet oxygen photosensitized by hypericin, kinetic study in nonionic micellar medium. J. Chim. Phys. Phys. Chim. Biol. 85, 971-977.
45. Darmanyan, A. P., L. Burel, D. Eloy and P. Jardon (1994) Singlet oxygen production by hypericin in various solvents. J. Chim. Phys. Phys. Chim. Biol. 91, 1774-1785.
46. Yamazaki, T., N. Ohta, I. Yamazaki and P. S. Song (1993) Excited state properties of hypericin: electronic spectra and fluorescence decay kinetics. J. Phys. Chem. 97, 7870-7875.
47. Freeman, D., F. Frolow, E. Kapinus, D. Lavie, G. Lavie, D. Meruelo and Y. Mazur (1994) Acidic properties of hypericin and its octahydroxy analogue in the ground and excited states. J. Chem. Soc. Chem. Commun. 891-892.
48. Ramaiah, D., A. Joy, N. Chandrasekhar, N. V. Eldho, S. Das, and M. V. George (1997) Halogenated squaraine dyes as potential photochemotherapeutic agents. Synthesis and study of photophysical properties and quantum efficiencies of singlet oxygen generation. Photochem. Photobiol. 65, 783-790.
49. de la Peña, D., C. Marti, S. Nonell, L. A. Martinez, and M. A. Miranda (1997) Time-resolved near infrared studies on singlet oxygen production by the photosensitizing 2-arylpropionic acids. Photochem. Photobiol. 65, 828-832.