Subcellular distributions and excited-state processes of hypericin in neurons

Photochemistry and Photobiology

Volumn 69, Issue 3, 1999, Pages 301-305

  English, Doug S ^a   Doyle, Robert T ^a   Petrich, Jacob W ^a   Haydon, Philip G ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; HYPERICIN; PERYLENE; PHOTOSENSITIZING AGENT;

ANIMAL; ARTICLE; CELL CULTURE; CELL FRACTIONATION; CYTOLOGY; FLUORESCENCE MICROSCOPY; HIPPOCAMPUS; METABOLISM; NERVE CELL; RAT;

ANIMALS; CELLS, CULTURED; HIPPOCAMPUS; MICROSCOPY, FLUORESCENCE; NEURONS; PERYLENE; PHOTOSENSITIZING AGENTS; RATS; SUBCELLULAR FRACTIONS;

EID: 0033094534     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1999.tb03290.x     Document Type: Article

References (41)

1. Carpenter, S. and G. A. Kraus (1991) Photosensitization is required for inactivation of equine infectious anemia virus by hypericin. Photochem. Photobiol. 53, 169-174.
2. 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 pseudohypericin. Proc. Nalt. Acad. Sci. USA 85, 5230-5234.
3. Lavie, G., F. Valentine, B. Levin, Y. Mazur, G. Gallo, D. Lavie, D. Weiner and D. Meruelo (1989) Studies of the mechanisms of action of the antiretroviral agents hypericin and pseudohypericin. Proc. Nalt. Acad. Sci. USA 86, 5963-5967.
4. Hudson, J. B., J. Zhou, J. Chen, L. Harris, L. Yip and G. H. N. Towers (1994) Hypocrellin, from Hypocrella bambuase, is phototoxic to human immunodeficiency virus. Photochem. Photobiol. 60, 253-255.
5. Meruelo, D., S. Degar, N. Amari, Y. Mazur, D. Lavie, B. Levin and G. Lavie (1992) Mode of action of hypericin as an antiretroviral agent and other relevant findings. In Natural Products as Antiviral Agents (Edited by C. K. Chu and H. G. Cutler), pp. 91-119. Plenum Press, New York.
6. Takahashi, I., S. Nakanishi, E. Kobayashi, H. Nakano, K. Suziki and T. Tamaoki (1989) Hypericin and pseudohypericin specifically inhibit protein kinase C: possible relation to their antiretroviral activity. Biochem. Biophys. Res. Commun. 165, 1207-1212.
7. Andreoni, A., A. Colasanti, P. Colasanti, M. Mastrocinque, P. Riccio and G. Roberti (1994) Laser photosensitization of cells by hypericin. Photochem. Photobiol. 59, 529-533.
8. 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. J. Neurosurg. 35, 705-710.
9. Thomas, C. and R. S. Pardini (1993) Oxygen dependence of hypericin-induced phototoxicity to EMT6 mouse mammary carcinoma cells. Photochem. Photobiol. 55, 831-837.
10. Linde, K., G. Ramirez, C. D. Mulrow, A. Pauls, W. Weidenhammer and D. Melchart (1996) St John's wort for depression - an overview and meta-analysis of randomised clinical trials. Br. Med. J. 313, 253-257.
11. Suzuki, O., Y. Katsumata, M. Oya, S. Bladt and H. Wagner (1984) Inhibition of monoamine oxidase by hypericin. Planta Med. 50, 272-274.
12. 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.
13. Diwu, Z. (1995) Novel therapeutic and diagnostic applications of hypocrellins and hypericins. Photochem. Photobiol. 61, 529-539.
14. Dets, S. M., A. Y. Joffe, A. N. Buryi, N. A. Denisov, I. S. Melnik and A. H. Raviez (1997) Hypericin-induced fluorescence in stomach cancer detection. SPIE 2972, 173-178.
15. Miskovsky, P., F. Sureau, L. Chinsky and P.-Y. Turpin (1995) Subcellular distribution of hypericin in human cancer cells. Photochem. Photobiol. 62, 546-549.
16. Fehr, M. J., M. A. McCloskey and J. W. Petrich (1995) Light-induced acidification by the antiviral agent hypericin. J. Am. Chem. Soc. 117, 1833-1836.
17. 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.
18. Chaloupka, R., F. Sureau, E. Kocisova and J. W. Petrich (1998) Hypocrellin A photosensitization involves an intracellular pH decrease in 3T3 cells. Photochem. Photobiol. 68, 44-50.
19. Bahls, F. H., R. Lartius, L. E. Trudeau, R. T. Doyle, Y. Fang, D. Witcher, K. Campbell and P. G. Haydon (1998) Contact-dependent regulation of N-type calcium channel subunits during synaptogenesis. J. Neurobiol. 35, 198-208.
20. Rich, R. L., Y. Chen, D. Neven, M. Négrerie, F. Gai and J. W. Petrich (1993) Steady-state and time-resolved fluorescence anisotropy of 7-azaindole and its derivatives. J. Phys. Chem. 97, 1781-1788.
21. Lown, J. W. (1997) Photochemistry and photobiology of perylenequinones. Can. J. Chem. 75, 99-119.
22. 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.
23. 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. (Submitted)
24. 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.
25. 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.
26. 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.
27. English, D. S., W. Zhang, G. A. Kraus and J. W. Petrich (1997) Excited-state photophysics of hypericin and its hexamethoxy analog, intramolecular proton transfer as a nonradiative process in hypericin. J. Am. Chem. Soc. 119, 2980-2986.
28. 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 agent. J. Phys. Chem. 101A, 3235-3240.
29. Sevenants, M. R. (1965) Pigments of Blepharisma undulans compared with hypericin. J. Protozool. 12, 240-245.
30. 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.
31. Das, K., D. S. English and J. W. Petrich (1997) Solvent dependence on the intracellular excited-state proton or hydrogen atom transfer in hypocrellin. J. Am. Chem. Soc. 119, 2763-2764.
32. 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. 101A, 3241-3245.
33. English, D. S., K. Das, K. D. Ashby, J. Park, J. W. Petrich and E. W. Castner, Jr. (1997) Confirmation of excited-state proton transfer and ground-state heterogeneity in hypericin by fluorescence upconversion. J. Am. Chem. Soc. 119, 11585-11590.
34. Dai, R., T. Yamazaki, I. Yamazaki and P.-S. Song (1995) Initial spectroscopic characterization of the ciliate photoreceptor stentorin. Biochim. Biophys. Acta 1231, 58-68.
35. Tao, N., Orlando, M., Hyon. J.-S., Gross, M. and P.-S. Song (1993) A new photoreceptor molecule from Stentor coeruleus. J. Am. Chem. Soc. 115, 2526-2528.
36. Wells, T. A., A. Losi, R. Dai, P. Scott, S.-M. Park, J. Golbeck and P.-S. Song (1997) Electron transfer quenching and photo-induced EPR of hypericin and the ciliate photoreceptor stentorin. J. Phys. Chem. A 101, 366-372.
37. Darmanyan, A. P., L. Burel, D. Eloy and P. Jardon, P. (1994) Singlet oxygen production by hypericin in various solvents. J. Chim. Phys. 91, 1774-1785.
38. Nenghui, W. and Z. Zhiyi (1992) Relationship between photosensitizing activities and chemical structure of hypocrellin A and B. J. Photochem. Photobiol. B Biol. 14, 207-217.
39. Diwu, Z. and J. W. Lowen (1993) Photosensitization with anticancer agents. 17. EPR studies of photodynamic action of hypericin: formation of semiquinone radical and activated oxygen species on illumination. Free Radicals Biol. Med. 14, 209-215.
40. Weiner, L. and Y. Mazur (1992) EPR studies of hypericin. Photogeneration of free radicals and superoxide. J. Chem. Soc. Perkin Trans. 2, 1439-1442.
41. 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.