Studies on the synthesis of two hydrophilic hypocrellin derivatives with enhanced absorption in the red spectral region and on their photogeneration of O2.- and O2(1Δg)

Journal of Photochemistry and Photobiology B: Biology

Volumn 71, Issue 1-3, 2003, Pages 43-50

  Lee, Hua Yang ^a   Chen, Shen ^a   Zhang, Man Hua ^a   Shen, Tao ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

Amino substituted hypocrellin B; EPR spectra; Photodynamic therapy; Singlet oxygen; Superoxide anion radical

Indexed keywords

ANTHRACENE DERIVATIVE; ETHANOLAMINE; HYPOCRELLIN A; HYPOCRELLIN B; HYPOCRELLIN B DERIVATIVE; SINGLET OXYGEN; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; BLEACHING; CONSTANTS AND COEFFICIENTS; CONTROLLED STUDY; DRUG ABSORPTION; DRUG SYNTHESIS; ELECTRON SPIN RESONANCE; HYDROPHILICITY; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOACTIVATION; PHOTODYNAMIC THERAPY; PHOTODYNAMICS; PHOTOSYNTHESIS; PRIORITY JOURNAL; QUANTUM YIELD; STRUCTURE ANALYSIS; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0141996315     PISSN: 10111344     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotobiol.2003.07.005     Document Type: Article

References (21)

1. N. Duran, P.S. Song, Hyporicin and its photodynamic action, J. Photochem. Photobiol. 43 (1986) 677.
2. G.A. Kraus, W. Zhang, M.J. Fehr, J. Petrick, Research at the interface between Chemistry and Virology: development of amolecular flashlight, Chem. Rev. 96 (1996) 523.
3. T. Reynolds, Photodynamic therapy expands its horizons, J. Natl. Cancer Inst. 89 (1997) 112.
4. J.B. Hudson, U. Imperial, R.P. Hauglan, Z.J. Diwu, Antiviral activities of photoactive perylenequinones, Photochem. Photobiol. 65 (1997) 352.
5. Z.J. Diwu, J.W. Lown, Photosensitization with anticancer agents 12 perylenequinonoid pigments: a novel type of singlet oxygen sensitizer, J. Photochem. Photobiol. A: Chem. 66 (1992) 66.
6. Y.Z. Hu, J.Y. An, L.J. Jiang, Studies of the sulfonation of hypocrellin A and the photodynamic actions of the product, J. Photochem. Photobiol. B: Biol. 17 (1993) 195.
7. Y.Z. Hu, J.Y. An, L.J. Jiang, Studies on the chelation of hypocrellin A with aluminum ion and the photodynamic action of the resulting complex, J. Photochem. Photobiol. B: Biol. 22 (1994) 219.
8. .OH) during the photosensitization of a water-soluble perylenequinone derivative, J. Photochem. Photobiol. B: Biol. 33 (1996) 51.
9. Z.J. Diwu, C.L. Zhang, J.W. Lown, Photosensitization with anticancer agents. 18. Perylenequinonoid pigments as potential photodynamatic therapeutic agents: preparation and photodynamic properties of amino-substituted hypocrellin derivatives, Anticancer Drug Des. 8 (1993) 129.
10. T. Wu, S.J. Xu, J.Q. Shen, A.M. Song, S. Chen, M.H. Zhang, T. Shen, New potential photodynamic therapeutic anticancer agents: synthesis and characterization of demethocy amino-substituted hypocrellins, Anticancer Drug Des. 15 (2000) 287.
11. S.J. Xu, S. Chen, M.H. Zhang, T. Shen, Cyclohexylamino-demethoxy-hypocrellin B and its photodynamic therapy decreases human pancreatic cancer in vitro, Biochim. Biophys. Acta 1523 (2000) 6.
12. T. Wu, J.Q. Shen, A.M. Song, S. Chen, M.H. Zhang, T. Shen, Photodynamicaction of amino substituted hypocrellin: EPR studies on the photogenerations of active oxygen and free radical species, J. Photochem. Photobiol. B: Biol. 57 (2000) 14.
13. K.H. Zhao, L.J. Jiang, Conversion of hypocrellion A in alkaline and neutral media, Youji Huaxue 9 (1989) 252.
14. C. Hadjur, A. Jeunet, P. Jardon, Photosensitization by hypercin: electron spin resonance (ESR) evidence for the formation of singlet oxygen and superoxide anion radicals in an in vitro model, J. Photochem. Photobiol. B: Biol. 26 (1994) 67.
15. Z.J. Diwu, J.W. Lown, Photosensitization by anticancer agents. 12. Perylenequinonoid pigments: a novel type of singlet oxygen sensitizer, J. Photochem. Photobiol. A: Chem. 64 (1992) 273.
16. Z.J. Diwu, C.L. Zhang, J.W. Lown, Photosensitization with anticancer agents. 15. Perylenequinonoid pigments as potential photodynamatic therapeutic agents: formation of semiquinone radicals and reactive oxygen species on illumination anticancer, J. Photochem. Photobiol. B: Biol. 18 (1993) 131.
17. Z.J. Diwu, M.H. Zhang, Research on the electronic spectra of hypocrellion A and B, Sinica Sci. B 2 (1989) 113.
18. K. Lang, M. Wagnarvoa, P. Stoka, W. Dameran, Reduction of dioxygen to superoxide photosensitized by anthraquinone-2-sulphonate, J. Photochem. Photobiol. A: Chem. 67 (1992) 187.
19. .- by benzoquinone in cyanoarmatic-sensitized photooxygenation, Tetrahedron Lett. 84 (1984) 2523.
20. M.J. Fehr, M.A. McCloskey, J.W. Petrick, Light-induced acidification by the antiviral agent hypericin, J. Am. Chem. Soc. 117 (1995) 1833.
21. K. Das, D.S. English, J.W. Petrick, Deuterium isotope effect on the excited-state photophysics of hypocrellin: evidence for proton or hydrogen atom transfer, J. Phys. Chem. A 101 (1997) 3241.