Synthesis and Optical Properties of Fluorine-Containing Phthalocyanine Conjugated with Glucofuranose and its Application to Photo-Dynamic Therapy

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  • MORI Satoru
    Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology
  • TOKUNAGA Etsuko
    Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology
  • HAYASHI Masamichi
    Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology
  • OBATA Tohru
    Department of Bioorganic Chemistry, School of Pharmacy, Aichi Gakuin University
  • TANAKA Motohiro
    Department of Bioorganic Chemistry, School of Pharmacy, Aichi Gakuin University
  • SHIBATA Norio
    Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology

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  • グルコフラノース部位を持つ含フッ素フタロシアニンの合成と分光学的性質および光線力学的療法への展開

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Abstract

<p>A novel fluorinated phthalocyanine 1a with four glucofuranoses at its peripheral positions was designed as a photosensitizer for photodynamic therapy of cancer. The target fluorinated phthalocyanine/glucofuranose conjugate 1a was synthesized by tetramerization of corresponding glucofuranose-attached fluorinated phthalonitrile 4 in the presence of zinc (II) acetate when heated. The optical and chemical properties of the target conjugate 1a were investigated by UV/Vis spectra, fluorescence, HPLC, MALDI-TOF MS, and partition coefficients. The biological (PDT) property of 1a was also examined via an in vitro assay using HT-1080 cells after exposure to light. All the properties of 1a were compared to the acetal analogue 2a and non-fluorinated counterparts 1b and 2b. Of note, the perfluorinated conjugate 1a showed a more efficient photo-dynamic effect than its non-fluorinated analogue 1b and their acetal analogues 2a,b in the in vitro cell assay.</p>

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