Narumi Atsushi, Tsuji Takahiro, Shinohara Kosuke, Yamazaki Hiromi, Kikuchi Moriya, Kawaguchi Seigou, Mae Tomoya, Ikeda Atsushi, Sakai Yuichi, Kataoka Hiromi, Inoue Masahiro, Nomoto Akihiro, Kikuchi Jun-ichi, Yano Shigenobu
Department of Polymer Science and Engineering, Graduate School of Science and Engineering, Yamagata University, Jonan 4-3-16, Yonezawa 992-8510, Japan.
Org Biomol Chem. 2016 Apr 14;14(14):3608-13. doi: 10.1039/c6ob00276e. Epub 2016 Mar 15.
Photoactive molecules with the frameworks of chlorin and/or porphyrin possessing four perfluorinated aromatic rings were conjugated with maltotriose (Mal3) via the nucleophilic aromatic substitution reaction and subsequent deprotection reaction of the oligosaccharide moieties. The resulting oligosaccharide-conjugated molecules are ultimately improved as compared to the previously reported monosaccharide-counterparts in terms of water-solubility. In particular, a water-soluble chlorin derivative surrounded by four Mal3 molecules showed an excellent biocompatibility, strong photoabsorption in the longer wavelength regions, and a very high photocytotoxicity. Thus, the present synthetic route combined with the use of an oligosaccharide was shown to be a straightforward strategy to develop a third generation photosensitizer for photodynamic therapy (PDT).
具有二氢卟吩和/或卟啉骨架且带有四个全氟芳香环的光活性分子通过亲核芳香取代反应以及随后寡糖部分的脱保护反应与麦芽三糖（Mal3）共轭。与先前报道的单糖对应物相比，所得的寡糖共轭分子在水溶性方面最终得到了改善。特别地，被四个Mal3分子包围的水溶性二氢卟吩衍生物表现出优异的生物相容性、在较长波长区域的强光吸收以及非常高的光细胞毒性。因此，结合使用寡糖的当前合成路线被证明是开发用于光动力疗法（PDT）的第三代光敏剂的直接策略。
