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Photosensitized oxidative damage of human serum albumin by water-soluble dichlorophosphorus(V) tetraphenylporphyrin

  • Ouyang, Dongyan (Department of Optoelectronics and Nanostructure Science, Graduate School of Science and Technology, Shizuoka University) ;
  • Hirakawa, Kazutaka (Department of Optoelectronics and Nanostructure Science, Graduate School of Science and Technology, Shizuoka University)
  • Received : 2015.06.21
  • Accepted : 2015.06.27
  • Published : 2015.06.30

Abstract

Biomolecular photo-damaging activity of a water-soluble cationic porphyrin was examined using human serum albumin (HSA), a water-soluble protein as a target biomolecule model by a fluorometry. Dichlorophosphorus(V) tetraphenylporphyrin ($Cl_2P(V)TPP$), was synthesized and used as a photosensitizer. This porphyrin could bind to HSA and cause the photosensitized oxidation of HSA through the singlet oxygen generation and the oxidative photo-induced electron transfer (ET). Near infrared emission spectroscopy demonstrated the photosensitized singlet oxygen generation by this porphyrin. Decrement of the fluorescence lifetime of $Cl_2P(V)TPP$ by HSA supported the ET mechanism. Furthermore, the estimated Gibb's energy indicated that the ET mechanism is possible in the terms of energy. Because oxygen concentration in cancer cell is relatively low, ET mechanism is considered to be advantageous for photosensitizer of photodynamic therapy.

Keywords

References

  1. Dolmans, D. E. J. G. J.; Fukumura, D.; Jain, R. K. Nat. Rev. Cancer 2003, 3, 380-387. https://doi.org/10.1038/nrc1071
  2. Castano, A. P.; Mroz, P.; Hamblin, M. R. Nat. Rev. Cancer 2006, 6, 535-545. https://doi.org/10.1038/nrc1894
  3. Hockel, M.; Vaupel, P. J. Natl. Cancer Inst. 2001, 93, 66-76. https://doi.org/10.1093/jnci/93.1.66
  4. Zhang, S.; Hosaka, M.; Yoshihara, T.; Negishi, K.; Iida, Y.; Tobita, S.; Takeuchi, T. Cancer Res 2010, 70, 4490-4498. https://doi.org/10.1158/0008-5472.CAN-09-3948
  5. Hirakawa, K. DNA damage through photo-induced electron transfer and photosensitized generation of reactive oxygen species. In: New Research on DNA Damage; Nova Science Publishers Inc.: New York, 2008, pp. 197-219.
  6. Hirakawa, K.; Segawa, H. J. Photochem. Photobiol. A: Chem. 1999, 123, 67-76. https://doi.org/10.1016/S1010-6030(99)00043-X
  7. Hirakawa, K.; Segawa, H. Photochem. Photobiol. Sci. 2010, 9, 704-709. https://doi.org/10.1039/b9pp00204a
  8. Hirakawa, K.;Fukunaga, N.; Nishimura, Y.; Arai T.; Okazaki, S. Bioorg. Med. Chem. Lett. 2013, 23, 2704-2707. https://doi.org/10.1016/j.bmcl.2013.02.081
  9. Hirakawa, K.; Umemoto, H.; Kikuchi, R.; Yamaguchi, H.; Nishimura, Y.; Arai, T.; Okazaki, S.; Segawa, H. Chem. Res. Toxicol. 2015, 28, 262-267. https://doi.org/10.1021/tx500492w
  10. Hirakawa, K.; Hirano, T. Nishimura, Y.; Arai, T.; Nosaka, Y. J. Phys. Chem. B 2012, 116, 3037-3044. https://doi.org/10.1021/jp300142e
  11. Usui, Y.; Kamogawa, K. Photochem. Photobiol. 1974, 19, 245-247. https://doi.org/10.1111/j.1751-1097.1974.tb06506.x
  12. Ogilby, P. R.; Foote, C. S. J. Am. Chem. Soc. 1983, 105, 3423-3430. https://doi.org/10.1021/ja00349a007
  13. Sima, J. Coord. Chem. Rev. 2006, 250, 2325-2334. https://doi.org/10.1016/j.ccr.2006.03.004
  14. Sulkowska. A.; Rownicka. J.; Bojko. B.; Sulkowski, W. J. Mol. Struct. 2003, 651-653, 133-140. https://doi.org/10.1016/S0022-2860(02)00642-7
  15. Hirakawa, K.; Azumi, K.; Nishimura, Y.; Arai, T.; Nosaka, Y.; Okazaki, S. J. Porphyrins Phthalocyanines 2013, 17, 56-62. https://doi.org/10.1142/S1088424612501258

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