Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis and Photodynamic Activities of Pyrazolyl and Cyclopropyl Derivatives of Purpurin-18 Methyl Ester and Purpurin-18-N-butylimide

  • Yoon, Il (PDT Research Institute, School of Nano System Engineering, Inje University) ;
  • Park, Ho-Sung (PDT Research Institute, School of Nano System Engineering, Inje University) ;
  • Cui, Bing Cun (PDT Research Institute, School of Nano System Engineering, Inje University) ;
  • Kim, Jung-Hwa (PDT Research Institute, School of Nano System Engineering, Inje University) ;
  • Shim, Young-Key (PDT Research Institute, School of Nano System Engineering, Inje University)
  • Received : 2010.09.14
  • Accepted : 2010.11.08
  • Published : 2011.01.20
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Abstract

The synthesis of new pyrazolyl and cyclopropyl derivatives of purpurin-18 methyl ester and purpurin-18-N-butylimide 1a, 1b, 2a, 2b and 8 is described. The new compounds were characterized by NMR, UV-vis spectroscopy and mass spectrometry. UV-vis spectra of the new compounds showed long wavelength absorption of ranges 692 - 708 nm ($\lambda_{max}$). Photodynamic effects of the chlorin derivatives 1a, 1b, 2a and 2b were investigated by WST-1 assay in A549 cells, and showed good photodynamic activities with high photocytotoxicity and low cytotoxicity in the dark. In comparison between pyrazolyl and cyclopropyl derivatives, purpurin-18 methyl ester compounds 1a and 1b showed comparable photocytotoxicity result of the cell viabilities, otherwise, pyrazolyl derivative of purpurin-18-N-butylimide 2a showed better cell viabilities than those of cyclopropyl derivative 2b. And cyclopropyl derivative of purpurin-18-N-butylimide 2b showed higher dark cytotoxicity than that of others.

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