Abstract
Based on their high photosensitivity, the potential medical application of fullerenes (C60 and C70) such as photodynamic therapy agents has been discussed for decades. Due to their high hydrophobicity, it is necessary to find a good method to solubilize fullerenes in water or water-miscible solvents for such application. We have been using a biocompatible and water-soluble polymer, poly(vinylpyrrolidone) (PVP) to prepare water-soluble C60/ or C70/PVP complex1 and C60- or C70-PVP conjugates2. 3 with efficient reactive oxygen species (ROSs) generation under visible light.4,5 However, in the clinical use, well-defined compounds with narrower molecular weight distribution are favored. In this study, we synthesized a RAFT reagent 1 for the preparation of well-defined PVP. The terminal moiety was converted to an amine 2 to connect to a C60 acid anhydride derivative 3 which was obtained through a Prato reaction.6 Obtained C60-PVP conjugate had a narrower molecular distribution, high water-solubility and photoinduced ROS generation.7 (1) Yamakoshi, Y.; Yagami, T.; Fukuhara, K.; Sueyoshi, S.; Miyata, N. J. Chem. Soc., Chem. Commun. 1994, 517. (2) Iwamoto, Y.; Yamakoshi, Y. Chem. Commun. 2006, 4805. (3) Oriana, S.; Aroua, S.; Söllner, J. O. B.; Ma, X.; Iwamoto, Y.; Yamakoshi, Y. Chem. Comm. 2013, 49, 9302. (4) Yamakoshi, Y.; Sueyoshi, S.; Fukuhara, K.; Miyata, N. J. Am. Chem. Soc. 1998, 120, 12367. (5) Yamakoshi, Y.; Umezawa, N.; Ryu, A.; Arakane, K.; Miyata, N.; Goda, Y.; Masumizu, T.; Nagano, T. J. Am. Chem. Soc. 2003, 125, 12803. (6) Aroua, S.; Schweizer, W. B.; Yamakoshi, Y. Org. Lett. 2014, 16, 1688. (7) Aroua, S.; Tiu, E. G. V.; Ayer, M.; Ishikawa, T.; Yamakoshi, Y. Polymer Chem. 2015, 6, 2616. Figure 1
Published Version
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