The Role of Oxygen in the Antiviral Activity of Hypericin and Hypocrellin

Photochemistry and Photobiology

Volumn 68, Issue 4, 1998, Pages 593-597

  Park, Jaehun ^a   English, Doug S ^a   Wannemuehler, Yvonne ^a   Carpenter, Susan ^a   Petrich, Jacob W ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE TRIPHOSPHATE; ANTIVIRUS AGENT; DRUG DERIVATIVE; HYPERICIN; HYPOCRELLIN A; OXYGEN; PERYLENE; QUINONE DERIVATIVE; SINGLET OXYGEN;

ANIMAL; ARTICLE; CHEMOLUMINESCENCE; DRUG EFFECT; EQUINE INFECTIOUS ANEMIA VIRUS; HORSE; LIGHT; MICROBIOLOGICAL EXAMINATION; PHOTOCHEMISTRY; RADIATION EXPOSURE;

ADENOSINE TRIPHOSPHATE; ANIMALS; ANTIVIRAL AGENTS; CHEMILUMINESCENT MEASUREMENTS; HORSES; INFECTIOUS ANEMIA VIRUS, EQUINE; LIGHT; MICROBIAL SENSITIVITY TESTS; OXYGEN; PERYLENE; PHOTOCHEMISTRY; QUINONES; SINGLET OXYGEN;

EID: 0032186303     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1998.tb02519.x     Document Type: Article

References (54)

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. Natl. 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. Natl. 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. Lopez-Bazzocchi, I., J. B. Hudson and G. H. N. Towers (1991) Antiviral activity of the photoactive plant pigment hypericin. Photochem. Photobiol. 54, 95-98.
6. Degar, S., A. M. Prince, D. Pascaul, G. Lavie, B. Levin, Y. Mazur, D. Lavie, L. S. Ehrlich, C. Carter and D. Meruelo (1992) Inactivation of the human immunodeficiency virus by hypericin: evidence for photochemical alterations of p24 and a block in uncoating. AIDS Res. Hum. Retroviruses 8, 1929-1936.
7. 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.
8. (1991) Treating AIDS with worts. Science 254, 522.
9. Thomas, C. and R. S. Pardini (1992) Oxygen dependence of hypericin-induced phototoxicity to EMT6 mouse mammary carcinoma cells. Photochem. Photobiol. 55, 831-837.
10. Thomas, C., R. S. MacGill, G. C. Miller and R. S. Pardini (1992) Photoactivation of hypericin generates singlet oxygen in mitochondria and inhibits succinoxidase. Photochem. Photobiol. 55, 47-53.
11. 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.
12. Kreitmair, H. (1950) Hypericum perforatum - das Johanniskraut. Pharmazie 5, 556-557.
13. 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, 253-258.
14. Suzuki, O., Y. Katsumata, M. Oya, S. Bladt and H. Wagner (1984) Inhibition of monoamine oxidase by hypericin. Planta Med. 50, 272-274.
15. Anker, L., R. Gopalakrishna, K. D. Jones, R. E. Law and W. T. Couldwell (1995) Hypericin in adjuvant brain tumor therapy. Drugs of the Future 20, 511-517.
16. 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.
17. 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.
18. 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.
19. 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.
20. 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. A. 101, 3235-3240.
21. 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 comparison with hypericin. J. Phys. Chem. 100, 18275-18281.
22. 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.
23. 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.
24. English, D., 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.
25. 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.
26. Carpenter, S., M. J. Fehr, G. A. Kraus and J. W. Petrich (1994) Chemiluminescent activation of the antiviral activity of hypericin: a molecular flashlight. Proc. Natl. Acad. Sci. USA 91, 12273-12277.
27. 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.
28. Duran, N. and P.-S. Song (1986) Hypericin and its photodynamic action. Photochem. Photobiol. 43, 677-680.
29. Diwu, Z. (1995) Novel therapeutic and diagnostic applications of hypocrellins and hypericins. Photochem. Photobiol. 61, 529-539.
30. Lown, J. W. (1997) Photochemistry and photobiology of perylenequinones. Can. J. Chem. 75, 99-119.
31. Jardon, P., N. Lazorchak and R. Gautron (1986) Propriétés du premier état triplet de l'hypericine étude par spectroscopie laser. J. Chim. Phys. 83, 311-315.
32. g photosensibilisée par l'hypericine étude cinétique en milieu micellaire non ionique. J. Chim. Phys. 85, 971-977.
33. Weiner, L. and Y. Mazur (1992) EPR studies of hypericin. Photogeneration of free radicals and superoxide. J. Chem. Soc. Perkin Trans. 1439-1442.
34. 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.
35. Malkin, J. and Y. Mazur (1993) Hypericin derived triplet states and transients in alcohols and water. Photochem. Photobiol. 57, 929-933.
36. Hudson, J. B., V. Imperial, R. P. Haugland and Z. Diwu (1997) Antiviral activities of photoreactive perylenequinones. Photochem. Photobiol. 65, 352-354.
37. Darmanyan, A., L. Burel, D. Eloy and P. Jardon (1994) Singlet oxygen production by hypericin in various solvents. J. Chim. Phys. 91, 1774-1785.
38. Fehr, M. J., S. L. Carpenter and J. W. Petrich (1994) The role of oxygen in the photoinduced antiviral activity of hypericin. Bioorg. Med. Chem. Lett. 4, 1339-1344.
39. Fehr, M. J., S. L. Carpenter, Y. Wannemuehler and J. W. Petrich (1995) Roles of oxygen and photoinduced acidification in the light-dependent antiviral activity of hypocrellin A. Biochemistry 34, 15845-15848.
40. 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.
41. Carpenter, S., L. H. Evans, M. Sevoian and B. Chesebro. (1987) Role of the host immune response in selection of equine infectious anemia virus variants. J. Virol. 61, 3783-3789.
42. g). J. Phys. Chem. 94, 4377-4378.
43. 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.
44. 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.
45. 2 protein has ion channel activity. Cell 69, 517-528.
46. Newell, K. J. and I. F. Tannock (1989) Reduction of intracellular pH as a possible mechanism for killing cell in acidic region of solid tumor, effects of carbonylcyanine-3-chlorophenylhydrazone. Cancer Res. 49, 4447-4482.
47. Newell, K. J., P. Wood, I. Stratford and I. Tannock (1992) Effect of agents which inhibit the regulation of intracellular pH on murine solid tumours. Br. J. Cancer 66, 311-317.
48. Barry, M. A., J. E. Reynold and A. Eastman (1993) Etoposide-induced apoptosis in human HL-60 cells is associated with intracellular acidification. Cancer Res. 53, 2349-2357.
49. Li, J. and A. Eastman (1995) Apoptosis in an interleukin-2-dependent cytotoxic lymphocyte cell line is associated with intracellular acidification. J. Biol. Chem. 270, 3203-3211.
50. Gottlieb, R. A., J. Nordberg. E. Skowronski and B. M. Babior (1996) Apoptosis induced in Jurkat cells by several agents is preceded by intracellular acidification. Proc. Natl. Acad. Sci. USA 93, 654-658.
51. Weiler, M., M. Trepel, C. Grimmel, M. Schabet, D. Bremen, S. Krajewski and J. C. Reed (1997) Hypericin-induced apoptosis of human malignant glioma cells is light-dependent, independent of bcl-2 expression, and does not require wild-type p53. Neurol. Res. 19, 459-470.
52. Gebicki, J. M. and B. H. J. Bielski (1981) Comparison of the capacities of the perhydroxyl and the superoxide radicals to initiate chain oxidation of linoleic acid. J. Am. Chem. Soc. 103, 7020-7022.
53. Ferradini, C. (1986) Espèces activées radicalaires de l'oxygène. Biochimie 68, 779-785.
54. - with unsaturated fatty acids. J. Biol. Chem. 258, 4759-4761.