Multidimensional reaction coordinate for the excited-state H-atom transfer in perylene quinones: Importance of the 7-membered ring in hypocrellins A and B

Photochemistry and Photobiology

Volumn 71, Issue 2, 2000, Pages 166-172

  Datta, Anindya ^a   Smirnov, Alexandre V ^a   Wen, Jin ^a   Chumanov, George ^a   Petrich, Jacob W ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN; HYPOCRELLIN A; HYPOCRELLIN B; PERYLENE QUINONE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; EXCITATION; FLUORESCENCE;

EID: 0034143180     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/0031-8655(2000)0710166MRCFTE2.0.CO2     Document Type: Article

References (27)

1. Durán, N. and P. S. Song (1986) Hypericin and its photodynamic action. Photochem. Photobiol. 43, 677-680.
2. Diwu, Z. and J. W. Lown (1990) Hypocrellins and their use in photosensitization. Photochem. Photobiol. 52, 609-616.
3. Diwu, Z. (1995) Novel therapeutic and diagnostic applications of hypocrellins and hypericins. Photochem. Photobiol. 61, 529-539.
4. Lown, J. W. (1997) 1996 Hoffman-LaRoche Award Lecture: Photochemistry and photobiology of perylenequinones. Can. J. Chem. 75, 99.
5. 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.
6. Gai, F., M. J. Fehr and J. W. Petrich (1993) Ultrafast excitedstate processes in the antiviral agent hypericin. J. Am. Chem. Soc. 115, 3384-3385.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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, 11585-11590.
12. 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.
13. 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.
14. 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.
15. 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.
16. 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.
17. 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.
18. 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.
19. Smirnov, A. V., D. B. Fulton, A. Andreotti and J. W. Petrich (1999) Exploring ground-state heterogeneity of hypericin and hypocrellin A and B: dynamic and 2D ROESY NMR. J. Am. Chem. Soc. 121, 7979-7988.
20. Smirnov, A. V., K. Das, D. S. English, Z. Wan, G. A. Kraus and J. W. Petrich (1999) Excited-state intramolecular H-atom transfer of hypericin and hypocrellin A investigated by fluorescence upconversion. J. Phys. Chem. (In press)
21. Fehr, M. J., M. A. McCloskey and J. W. Petrich (1995) Lightinduced acidification by the antiviral agent hypericin. J. Am. Chem. Soc. 117, 1833-1836.
22. 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.
23. 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.
24. Collins, C. J. and N. S. Bowman (1970) Isotope Effects in Chemical Reactions. Van Nostrand Reinhold Co., New York.
25. Petrich, J. W., M. S. Gordon and M. Cagle (1998) Structure and energetics of ground-state hypericin: comparison of experiment and theory. J. Phys. Chem. A 102, 1647-1651.
26. Birks, J. B. (1970) Photophysics of Aromatic Molecules. Wiley-Interscience, London.
27. Viswanath, D. S. and G. Natarajan (1989) Dara Book on the Viscosity of Liquids. Hemisphere Publishing Company, New York.