Effect of pH on the fluorescence and absorption spectra of hypericin in reverse micelles

Photochemistry and Photobiology

Volumn 72, Issue 5, 2000, Pages 612-618

  Chowdhury, P K ^a   Ashby, K D ^a   Datta, A ^a   Petrich, J W ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DOCUSATE SODIUM; HEPTANE; HYPERICIN; SUCCINIC ACID DERIVATIVE;

ARTICLE; ENVIRONMENT; FLUORESCENCE; MICELLE; PH;

HYDROGEN-ION CONCENTRATION; MICELLES; MODELS, MOLECULAR; PERYLENE; PHOTOCHEMISTRY; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY;

EID: 0034335321     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/0031-8655(2000)072<0612:EOPOTF>2.0.CO;2     Document Type: Article

References (66)

1. Duran, N. and P. S. Song (1986) Hypericin and its photodynamic action. Photochem. Photobiol. 43, 677-680.
2. Lown, J. W. (1997) Photochemistry and photobiology of perylenequinones. Can. J. Chem. 75, 99-119.
3. Diwu, Z. (1995) Novel therapeutic and diagnostic applications of hypocrellins and hypericins. Photochem. Photobiol. 61, 529-539.
4. Kraus, G. A., W. Zhang, M. J. Fehr, J. W. Petrich, Y. Wannemuehler and S. Carpenter (1996) Research at the interface between chemistry and virology: development of a molecular flashlight. Chem. Rev. 96, 523-535.
5. Falk, H. (1999) From the photosensitizer hypericin to the photoreceptor stentorin - the chemistry of phenanthroperylene quinones. Angew. Chem. Int. Ed. 38, 3116-3136.
6. Meruelo, D., G. Lavie and D. Lavie (1988) Therapeutic agents with dramatic antiretroviral activity and little toxicity at effective doses: aromatic polycyclic diones hypericin and pseudo-hypericin. Proc. Natl. Acad. Sci. USA 85, 5230-5234.
7. Lenard, J., A. Rabson and R. Vanderoef (1993) Photodynamic inactivation of infectivity of human immunodeficiency virus and other enveloped viruses using hypericin and rose bengal: inhibition of fusion and syncytia formation. Proc. Natl. Acad. Sci. USA 90, 158-162.
8. Hudson, J. B., J. Zhou, J. Chen, L. Harris, L. Yip and G. H. N. Towers (1994) Hypocrellin, from Hypocrella bambusae, is phototoxic to human immunodeficiency virus. Photochem. Photobiol. 60, 253-255.
9. Couldwell, W. T., R. Gopalakrishna, D. R. Hinton, S. He, M. H. Weiss, R. E. Law and M. L. Apuzzo (1994) Hypericin: a potential antiglioma therapy. Neurosurgery 35, 705-710.
10. Anker, L., R. Gopalakrishna, K. D. Jones, R. E. Law and W. T. Couldwell (1995) Hypericin in adjuvant brain tumor therapy. Drugs Future 20, 511-517.
11. Zhang, W., R. E. Law, D. R. Hinton and W. T. Couldwell (1997) Inhibition of human malignant glioma cell motility and invasion in vitro by hypericin, a potent protein kinase C inhibitor. Cancer Lett. 120, 31-38.
12. Gai, F., M. J. Fehr and J. W. Petrich (1993) Ultrafast excited-state processes in the antiviral agent hypericin. J. Am. Chem. Soc. 115, 3384-3385.
13. Gai, F., M. J. Fehr and J. W. Petrich (1994) Observation of excited-state tautomerization in the antiviral agent hypericin and identification of its fluorescent species. J. Phys. Chem. 98, 5784-5795.
14. Gai, F., M. J. Fehr and J. W. Petrich (1994) Role of solvent in excited-state proton transfer in hypericin. J. Phys. Chem. 98, 8352-8358.
15. Das, K., D. S. English, M. J. Fehr, A. V. Smirnov and J. W. Petrich (1996) Excited-state processes in polycyclic quinones: the light-induced antiviral agent, hypocrellin, and a comparison with hypericin. J. Phys. Chem. 100, 18275-18281.
16. Das, K., D. S. English and J. W. Petrich (1997) Deuterium isotope effect on the excited-state photophysics of hypocrellin: evidence for proton or hydrogen atom transfer. J. Phys. Chem. A 101, 3241-3245.
17. Das, K., D. S. English and J. W. Petrich (1997) Solvent dependence on the intramolecular excited-state proton or hydrogen atom transfer in hypocrellin. J. Am. Chem. Soc. 119, 2763-2764.
18. Das, K., A. V. Smirnov, M. D. Snyder and J. W. Petrich (1998) Picosecond linear dichroism and absorption anisotropy of hypocrellin: toward a unified picture of the photophysics of hypericin and hypocrellin. J. Phys. Chem. B. 102, 6098-6106.
19. Das, K., E. Dertz, J. Paterson, W. Zhang, G. A. Kraus and J. W. Petrich (1998) Hypericin, hypocrellin, and model compounds: steady-state and time-resolved fluorescence anisotropies. J. Phys. Chem. B 102, 1479-1484.
20. Das, K., A. V. Smirnov, J. Wen, P. Miskovsky and J. W. Petrich (1999) Photophysics of hypericin and hypocrellin A in complex with subcellular components: interactions with human serum albumin. Photochem. Photobiol. 69, 633-645.
21. Das, K., K. Ashby, J. Wen and J. W. Petrich (1999) The temperature dependence of the excited-state intramolecular proton transfer reaction in hypericin and hypocrellin A. J. Phys. Chem. B 103, 1581-1585.
22. English, D. S., K. Das, K. D. Ashby, J. Park, J. W. Petrich and E. W. J. Castner (1997) Confirmation of excited-state proton transfer and ground-state heterogeneity in hypericin by fluorescence upconversion. J. Am. Chem. Soc. 119, 11 585-11 590.
23. English, D. S., K. Das, J. M. Zenner, W. Zhang, G. A. Kraus, R. C. Larock and J. W. Petrich (1997) Hypericin, hypocrellin, and model compounds: primary photoprocesses of light-induced antiviral agents. J. Phys. Chem. A 101, 3235-3240.
24. Petrich, J. W. (2000) Excited-state intramolecular H-atom transfer in nearly symmetrical perylene quinones: hypericin, hypocrellin, and their analogs. Int. Rev. Phys. Chem. (In press)
25. Sureau, F., P. Miskovsky, L. Chinsky and P. Y. Turpin (1996) Hypericin-induced cell photosensitization involves an intracellular pH decrease. J. Am. Chem. Soc. 118, 9484-9487.
26. English, D. S., R. T. Doyle, J. W. Petrich and P. G. Haydon (1999) Subcellular distributions and excited state processes of hypericin in neurons. Photochem. Photobiol. 69, 301-305.
27. Wong, M., J. K. Thomas and M. Gratzel (1976) Fluorescence probing of inverted micelles. The state of solubilized water clusters in alkane/AOT solution. J. Am. Chem. Soc. 98, 2391-2397.
28. Park, H.-R., H.-C. Lee, T. H. Kim, J.-K. Lee, K. Yang and K.-M. Bark (2000) Spectroscopic properties of fluoroquinoline antibiotics and nanosecond solvation dynamics of Aerosol-OT micelles. Photochem. Photobiol. 71, 281-293.
29. Rehak, H. F. E. a. J. (1976) On the formation of water/oil-microemulsions. Helv. Chim. Acta 59, 2883-2891.
30. Day, R. A., B. H. Robinson, J. Clarke and V. Doherty (1979) Characterization of water containing reversed micelles by viscosity and dynamic light scattering methods. J. Chem. Soc. Faraday Trans. 1 75, 132-139.
31. Mitchell, D. J. and B. W. Ninham (1981) Micelles, vesicles and microemulsions. J. Chem. Soc. Faraday Trans. 2 77, 601-629.
32. Zulauf, M. and H. F. Eicke (1979) Inverted micelles and microemulsions in the ternary system H2O/aerosol-OT/isooctane as studied by photon correlation spectroscopy. J. Phys. Chem. 83, 480-486.
33. Zinsli, P. E. (1979) Inhomogeneous interior of aerosol-OT microemulsions probed by fluorescence and polarization decay. J. Phys. Chem. 83, 3223-3231.
34. Shinoda, K., H. Kunieda, Arai and H. Saijo (1984) Principles of attaining very large solubilization (microemulsion): inclusive understanding of the solubilization of oil and water in aqueous and hydrocarbon media. J. Phys. Chem. 88, 5126-5129.
35. Jain, T. J., M. Varshney and A. Maitra (1989) Structural studies of aerosol-OT reverse micellar aggregates by FT-IR spectroscopy. J. Phys. Chem. 93, 7408-7416.
36. Eastoe, J., W. K. Young and B. H. Robinson (1990) Scattering studies of microemulsions in low-density alkanes. J. Chem. Soc. Faraday Trans. 86, 2883-2889.
37. Mukherjee, K., S. P. Moulik and D. C. Mukherjee (1993) Thermodynamics of micellization of aerosol-OT in polar and non-polar solvents. A calorimetric study. Langmuir 9, 1727-1730.
38. Hauser, H., G. Hearing, A. Pande and P. L. Luisi (1989) Interaction of water with sodium bis(2-ethyl-1-hexyl) sulfosuccinate in reversed micelles. J. Phys. Chem. 93, 7869-7876.
39. Luisi, P. L. (1985) Enzymes hosted in reverse micelles in hydrocarbon solution. Angew. Chem. Int. Ed. Engl. 24, 439-450.
40. 2O in reversed micelles. J. Am. Chem. Soc. 99, 4730-4736.
41. Frank, S. G., Y. H. Shaw and N. C. Lin (1973) Proton magnetic resonance study of aerosol-OT-water-electrolyte-n-octane systems. J. Phys. Chem. 77, 239-241.
42. Ekwall, P., L. Mandell and K. Fontell (1970) Some observations on binary and ternary aerosol-OT systems. J. Colloid Interface Sci. 33, 215-235.
43. Matthews, M. B. and J. E. Hirschhorn (1953) Solubilization and micelle formation in a hydrocarbon medium. J. Colloid Interface Sci. 8, 86-96.
44. Maitra, A. (1984) Determination of size parameters of water-aerosol OT-oil reverse micelles from their nuclear magnetic resonance data. J. Phys. Chem. 88, 5122-5125.
45. Menger, F. M., J. A. Donohue and R. F. Williams (1973) Catalysis in water pools. J. Am. Chem. Soc. 95, 286-288.
46. Robinson, B. H., C. Toprakcioglu and J. C. Dore (1984) Small-angle neutron scattering study of microemulsions stabilized by aerosol-OT. J. Chem. Soc. Faraday Trans. 1 80, 13-27.
47. Cassin, G., J. P. Badiali and M. P. Pileni (1995) AOT reverse micelles: a depletion model. J. Phys. Chem. 99, 12 941-12 946.
48. Belletete, M., M. Lachapelle and G. Durocher (1990) Polarity of AOT reverse micellar interfaces: use of the preferential solvation concepts in the evaluation of the effective dielectric constants. J. Phys. Chem. 94, 5337-5341.
49. Assih, T., F. Larche and P. Delord (1982) Evolution of the radius of the inverse micelles at high dilution in the aerosol-OT/water/n-decane system. J. Colloid Interface Sci. 89, 35-39.
50. Mandal, D., A. Datta, S. K. Pal and K. Bhattacharyya (1998) Solvation dynamics of 4-aminophthalimide in water-in-oil microemulsion of Triton-X in mixed solvents. J. Phys. Chem. B 102, 9070-9073.
51. Sarkar, N., K. Das, A. Datta, S. Das and K. Bhattacharyya (1996) Solvation dynamics of coumarin 480 in reverse micelles. Slow relaxation of water molecules. J. Phys. Chem. 100, 10523-10527.
52. Sarkar, N., A. Datta, S. Das and K. Bhattacharyya (1996) Solvation dynamics of coumarin 480 in reverse micelles. J. Phys. Chem. 100, 15 483-15 486.
53. Eloy, D., A. Le Pellec and P. Jardon (1996) Protonation and deprotonation of hypericin in the ground state and the first excited singlet state in a nonionic micellar medium. J. Chim. Phys. Phys.-Chim. Biol. 93, 442-457.
54. Bouirig, H., D. Eloy and P. Jardon (1993) Self-quenching of fluorescence and triplet-triplet absorption of hypericin in liposomes of dipalmitoylphosphatidylcholine. J. Chim. Phys. Phys.-Chim. Biol. 90, 2021-2038.
55. Racinet, H., P. Jardon and R. Gautron (1988) Formation d'oxygène sigulet photosensibilisée par l'hypericine étude cinétique en milieu micillaire non ionique. J. Chim. Phys. 85, 971-977.
56. Jardon, P. and R. Gautron (1989) Photophysical properties of hypericin in solution and in micellar dispersion. J. Chim. Phys. Phys.-Chim. Biol. 86, 2173-2190.
57. Burel, L., P. Jardon and J.-C. Lepretre (1997) Electrochemical behavior of hypericin in aqueous liposome and dimethyl sulf-oxide media. New J. Chem. 21, 399-403.
58. Bouirig, H., D. Eloy and P. Jardon (1992) Formation and reactivity of the singlet oxygen photosensitized by hypericin in the liposomes of dipalmitoylphosphatidylcholine. Evidence of delayed oxidation. J. Chim. Phys. Phys.-Chim. Biol. 89, 1391-1411.
59. 1H NMR study of deprotonation and complexation of 2,2′-dihydroxybiphenyl derivatives. J. Chim. Phys. 89, 549-557.
60. Altmann, R. and H. Falk (1997) The deprotonation and protonation equilibria of a hypericin derivative in aqueous solution. Monatsh. Chem. 128, 571-583.
61. Falk, H., J. Meyer and M. Oberreiter (1992) Deprotonation and protonation of hydroxyphenanthroperylenes. Monatsh. Chem. 123, 277-284.
62. 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.
63. Gerson, F., G. Gescheidt, P. Haering, Y. Mazur, D. Freeman, H. Spreitzer and J. Daub (1995) Electron-acceptor properties of hypericin and its salts: an ESR/ENDOR and electrochemical study. J. Am. Chem. Soc. 117, 11 861-11 866.
64. Darmanyan, A. P., W. S. Jenks, D. Eloy and P. Jardon (1999) Quenching of excited triplet state hypericin with energy acceptors and donors of electrons. J. Phys. Chem. B 103, 3323-3331.
65. Fleming, G. R. (1986) Relaxation processes in liquids and solutions. In Chemical Applications of Ultrafast Spectroscopy, Chap. 6, pp. 124-235. Oxford University Press, London.
66. Wittouck, N., R. M. Negri, M. Ameloot and F. C. De Schryver (1994) AOT reversed micelles investigated by fluorescence anisotropy of cresyl violet. J. Am. Chem. Soc. 116, 10 601-10 611.