DOI QR코드

DOI QR Code

Comparison of Photophysical and Photochemical Properties of Khellin and 8-Methoxypsoralen

  • Ho Kwon Kang (Department of Agricultural Chemistry, Sunchon National University) ;
  • Eun Ju Shin (Department of Chemistry, Sunchon National University) ;
  • Sang Chul Shim (Department of Chemistry, Korea Advanced Institute of Science and Technology)
  • Published : 1991.10.20

Abstract

The photophysical and photochemical properties of khellin were compared with those of 8-methoxypsoralen (8-MOP). Quantum yields of fluorescence and triplet formation decreases as solvent polarity increases, which is opposite to 8-MOP, and photocycloadditivity of khellin to olefins is much lower than that of 8-MOP. Electron ejection from khellin by laser flash was not observed, but observed from 8-MOP. As models of 4',5'-monoadducts of khellin or 8-MOP with thymine base, khellin<>dimethylfumarate 4',5'-monoadduct (KDF) was also compared with 8-MOP<>thymidine 4',5'-monoadduct (F-2) in those properties to give some insight on the second-step biadduct formation resulting in cross-links of DNA duplex. KDF and F-2 were very similar to khellin and 8-MOP in photophysical properties, respectively. However, KDF did not form adducts with various olefins, and thus it is thought that 2,3-double bond of chromone moiety in khellin is hardly reactive in contrast with 3,4-double bond of coumarin moiety in 8-MOP. These results indicate that khellin is fairly photostable compound, a poor type Ⅰ photodynamic sensitizer and producer of ${O_2}^{-}$ which is some cause of phototoxic erythemal reactions and undesirable side effects. Therefore khellin is safer to use than 8-MOP in photochemotherapy of some skin diseases. Although khellin is much less reactive than 8-MOP, khellin must be also a monofunctional drug. Since khellin is, however, as effective as 8-MOP in photochemotherapy of some skin diseases, it is suggested that khellin may be different from 8-MOP in the action mechanism.

Keywords

References

  1. J. Invest. Dermatol. v.32 J. A. Elliott, Jr.
  2. New Engl. J. Med. v.291 J. A. Parrish;T. B. Fitzpatrick;L. Tanebaum;M. A. Pathak
  3. J. Mol. Biol. v.116 C. -K. J. Shen;T. -S. Hsieh;J. C. Wang;J. E. Hearst
  4. Proc. Natl. Acad. Sci. USA v.73 C. -K. J. Shen;J. E. Hearst
  5. Photochem. Photobiol. v.50 D. Averbeck
  6. Photochem. Photobiol. v.29 P. -S. Song;K. J. Tapley, Jr.
  7. J. Am. Chem. Soc. v.103 K. Straub;D. Kanne;J. E. Hearst;H. Rapoport
  8. J. Am. Chem. Soc. v.104 D. Kanne;K. Straub;J. E. Hearst;H. Rapoport
  9. Nature v.283 B. A. Bridges;G. H. Strauss
  10. J. Am. Chem. Soc. v.72 A. Schonberg;A. Sina
  11. Biochim. Biophys. Acta v.475 E. Cassuto;N. Gross;E. Bardwell;P. Howard-Flanders
  12. Photochem. Photobiol. v.38 B. F. Aveysekera;Z. Abramowski;G. H. N. Towers
  13. Photochem. Photobiol. v.33 D. A. Grekin;J. H. Epstein
  14. Can. J. Bot. v.62 G. H. N. Towers
  15. Arch. Dermatol. v.100 J. E. Fultons, Jr.;J. Leyden;C. Papa
  16. Arch. Dermatol. v.93 T. B. Fitzpatrick;K. A. Arndt;A. M. El-Mofty;M. A. Pathak
  17. Dermatologics v.165 A. Abdel-Fattah;M. N. Aboul-Enein;G. M. Wassel;B. S. El-Menshawi
  18. Photochem. Photobiol. v.39 B. Ortel;A. Tanew;K. Wolff;H. Honigsmann
  19. J. Invest. Dermatol. v.90 P. Morliere;H. Honigsmann;D. Averbeck;D. Dardalhon;G. Huppe;B. Ortel;R. Santus;L. Dubertret
  20. J. Photochem. Photobiol., B: Biology v.7 L. Trabalzini;P. Martelli;L. Bovalinin;F. Dall`Acqua;E. Sage
  21. J. Am. Chem. Soc. v.95 W. W. Mantulin;P. -S. Song
  22. Photochem. Photobiol. v.32 B. J. Parson
  23. Photochem. Photobiol. v.27 R. V. Bensasson;E. J. Land;C. Salet
  24. Photochem. Photobiol. v.39 R. V. Bensasson;O. Chalvet;E. J. Land;R. C. Ronfard-Haret
  25. Photochem. Photobiol. v.29 R. W. Sloper;T. G. Truscott;E. J. Land
  26. Photochem. Photobiol. v.37 M. Craw;R. V. Bensasson;J. C. Ronfard-Heret;M. T. Sa E Melo;T. G. Truscott
  27. Bull. Korean Chem. Soc. v.8 S. C. Shim;H. K. Kang
  28. Bull. Korean Chem. Soc. v.10 H. K. Kang;S. C. Shim
  29. J. Photochem. Photobiol., A: Chemistry v.52 H. K. Kang;E. J. Shin;S. C. Shim
  30. Bull. Korean Chem. Soc. v.5 S. C. Shim;H. K. Kang
  31. Photochem. Photobiol. v.38 S. C. Shim;Y. Z. Kim
  32. Purification of Laboratory Chemicals(2nd ed.) D. D. Perrin;W. L. F. Armarego;D. R. Perrin
  33. Chem. Lett. M. Sasaki;T. Sakada;M. Sukigara
  34. J. Chem. Phys. v.68 W. A. Wassam, Jr.;E. C. Lim
  35. J. Chem. Phys. v.69 W. A. Wassam, Jr.;E. C. Lim
  36. J. Am. Chem. Soc. v.104 T. -I. Lai;B. T. Lim;E. C. Lim
  37. Photochem. Photobiol. v.30 M. T. Sa E Melo;M. T. D. Averbeck;R. V. Bensasson;E. J. Land;C. Salet
  38. J. Photochem. v.37 S. C. Shim;H. K. Kang;D. K. Park;E. J. Shin
  39. J. Photochem. Photobiol. v.45 S. C. Shim;H. K. Kang
  40. Bull. Korean Chem. Soc. v.7 S. C. Shim;H. K. Kang

Cited by

  1. Photoionization and Photosensitized Electron-Transfer Reactions of Psoralens and Coumarins1 vol.102, pp.28, 1991, https://doi.org/10.1021/jp9802026
  2. The family of furocoumarins: Looking for the best photosensitizer for phototherapy vol.199, pp.1, 1991, https://doi.org/10.1016/j.jphotochem.2008.04.013
  3. Photophysics and photochemistry of aflatoxins B1 and B2 vol.10, pp.10, 1991, https://doi.org/10.1039/c1pp05103b