Photosensitization of hypomycin B - A novel perylenequinonoid pigment with only one intramolecular hydrogen bond

Photochemistry and Photobiology

Volumn 74, Issue 2, 2001, Pages 191-195

  Zhang, Hong Yu ^a,b   Liu, Wei ^c   Liu, Wei Zhong ^d   Xie, Jin Lun ^e  

^a Zibo University   (China)

^b SHANDONG NORMAL UNIVERSITY   (China)

^c Mengzi Teachers' Institute   (China)

^d BINZHOU MEDICAL UNIVERSITY   (China)

^e YUNNAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYL GROUP; HYPOCRELLIN A; HYPOMYCIN B; OXYGEN; PIGMENT; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ACIDIFICATION; ANALYTIC METHOD; CONFERENCE PAPER; ELECTRON SPIN RESONANCE; FLUORESCENCE SPECTROSCOPY; HYDROGEN BOND; LIGHT; PHOTODYNAMIC THERAPY; PHOTOSENSITIVITY; PHOTOSENSITIZATION; SPIN TRAPPING;

HUMANS; HYDROGEN BONDING; OXYGEN; PERYLENE; PHOTOCHEMISTRY; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; QUINONES; SINGLET OXYGEN; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY; SUPEROXIDES;

EID: 0035437557     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/0031-8655(2001)074<0191:POHBAN>2.0.CO;2     Document Type: Conference Paper

References (46)

1. Duran, N. and P. S. Song (1986) Hypericin and its photodynamic action. Photochem. Photobiol. 43, 677-680.
2. Jiang, L. J. (1990) Structure, character, photochemical reaction and reaction mechanisms of hypocrellin (I) - structure and character of hypocrellin. Chin. Sci. Bull. 35, 1608-1616. [In Chinese]
3. Jiang, L. J. (1990) Structure, character, photochemical reaction and reaction mechanisms of hypocrellin (II) - reaction of hypocrellin. Chin. Sci. Bull. 35, 1681-1690. [In Chinese]
4. Diwu, Z. J. and J. W. Lown (1990) Hypocrellins and their uses in photosensitization. Photochem. Photobiol. 52, 609-616.
5. Diwu, Z. J. and J. W. Lown (1994) Phototherapeutic potential of alternative photosensitizers to porphyrins. Pharmacol. Ther. 63, 1-35.
6. Diwu, Z. J. (1995) Novel therapeutic and diagnostic applications of hypocrellins and hypericins. Photochem. Photobiol. 61, 529-539.
7. Zhang, H. Y. and Z. Y. Zhang (1999) The structure-activity relationship and broad prospects in applications of photosensitization of perylenequinonoid derivatives. Adv. Free Radic. Life Sci. 7, 41-47. [In Chinese]
8. Falk, H. (1999) From the photosensitizer hypericin to the photoreceptor stentorian - the chemistry of phenanthroperylene quinones. Angew. Chem., Int. Ed. Engl. 38, 3116-3136.
9. 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.
10. Gai, F., M. J. Fehr and J. W. Petrich (1994) Observation of excited-state tautomerization in the antiviral agent hypericin and identification of its fluorescence species. J. Phys. Chem. 98, 5784-5795.
11. 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.
12. 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.
13. 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.
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. 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.
16. 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.
17. 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.
18. English, D. S., K. Das, K. D. Ashby, J. Park, J. W. Petrich and E. W. Castner (1997) Conformation of excited-state proton transfer and ground-state heterogeneity in hypericin by fluorescence upconversion. J. Am. Chem. Soc. 119, 11585-11590.
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. 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.
21. 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.
22. Das, K., K. D. Ashby, J. Wen and J. W. Petrich (1999) Temperature dependence of the excited-state intramolecular proton transfer reaction in hypericin and hypocrellin A. J. Phys. Chem. B 103, 1581-1585.
23. Zhang, H. Y. and Z. Y. Zhang (1998) Theoretical study of intramolecular proton transfer of perylenequinone. Sci. China, Ser. B 41, 85-90.
24. Zhang, H. Y. (1999) Variance of charges in the process of isomerization of perylenequinone. J. Photochem. Photobiol. A: Chem. 126, 27-30.
25. Zhang, H. Y. (1998) Changes of dipole moment in intramolecular proton transfer process of perylenequinone. Chin. Sci. Bull. 43, 1380-1384.
26. 2-substituted perylenequinone. Dyes Pigments 47, 277-284.
27. Smirnov, A., D. B. Fulton, A. Andreotti and J. W. Petrich (1999) Exploring ground-state heterogeneity of hypericin and hypocrelin A and B: dynamic and 2D ROESY NMR study. J. Am. Chem. Soc. 121, 7979-7988.
28. Diwu, Z. J. and J. W. Lown (1993) Photosensitization with anticancer agents 15. Perylene-quinonoid pigments as potential photodynamic therapeutic agents: formation of semiquinone radicals and reactive oxygen species on illumination. J. Photochem. Photobiol. B: Biol. 18, 131-143.
29. Zhang, H. Y., Z. Y. Zhang, D. H. Wang and M. F. Li (1996) Comparison of photosensitization between hypocrellin A and cercosporin in homogeneous and heterogeneous system. Photogr. Sci. Photochem. 14, 144-149. [In Chinese]
30. Zhang, H. Y., Z. Y. Zhang, Q. Wan and D. H. Wang (1997) Influence of bromination on activity of photosensitization of hypocrellin B. J. Radiat. Res. Radiat. Process. 15, 75-79. [In Chinese]
31. Zhang, H. Y., H. X. Zhao and Z. Y. Zhang (1997) Studying dynamic process of photosensitization by ESR method. Sci. China, (Ser. C.) 40, 356-362.
32. Zhang, H. Y. (1998) Quantum chemistry calculation study on photosensitization of perylenequinonoid derivatives. Acta Biochim. Biophys. Sin. 30, 272-276. [In Chinese]
33. Zhang, H. Y. and D. Z. Chen (2000) Mechanism for intramolecular proton transfer involving hypericin. Dyes Pigments 46, 17-21.
34. Liu, W. Z. (2000) Fermentation and structure determination of hypomycin B. M.D. thesis, Yunnan University.
35. Liu, W. Z., Y. T. Chen and J. L. Xie (2000) Studies on solid state fermentation technology of a fungus producing perylenequinones. J. Yunnan Univ., Nat. Sci. Ed. 22, 389-391. [In Chinese]
36. Liu, W. Z., L. Y. Ma, C. Li, Y. T. Chen and J. L. Xie (2001) Structural elucidation of a new perylenequinone. Acta Pharmacol. Sin. 36, 313-314. [In Chinese]
37. Zhang, H. Y. and Z. Y. Zhang (1997) Determination of pKa values of perylenequinonoid photosensitizer in excited state. Chin. Sci. Bull. 42, 2005-2009.
38. 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.
39. He, Y. Y., J. Y. An and L. J. Jiang (1999) pH effect on the spectroscopic behavior and photoinduced generation of semiquinone anion radical of hypocrellin B. Dyes Pigments 41, 79-87.
40. Rohatgi-Mukherjee, K. K. (1991) Fundamentals of Photochemistry. Science Press, Beijing. [In Chinese]
41. 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.
42. 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.
43. 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.
44. Chaloupka, R., F. Sureau, E. Kocisova and J. W. Petrich (1998) Hypocrellin A photosensitization involves an intramolecular pH decrease in 3T3 cells. Photochem. Photobiol. 68, 44-50.
45. Diwu, Z. J. and J. W. Lown (1992) Photosensitization by anticancer agents. 12. Perylenequinonoid pigments, a novel type of singlet oxygen sensitizer. J. Photochem. Photobiol. A: Chem. 64, 273-287.
46. Diwu, Z. J., L. J. Jiang and M. H. Zhang (1989) The electronic spectra of hypocrellin A, B, and their derivatives. Sci. Sin. B 32, 113-120. [In Chinese]