Bulletin of the Korean Chemical Society

  • 제12권5호
  • /
  • Pages.554-559
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  • 1991
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  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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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)
  • 발행 : 1991.10.20
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초록

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.

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피인용 문헌

  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