The photodynamic action is initiated by the absorption of a photon followed by many competing radiative and nonradiative reactions which ultimately result in the oxidation and degradation of vital biomolecules (1). Molecular oxygen plays a key role in propagation the initial molecular damage, resulting in vascular collapse, tissue destruction, cell death. The photodynamic therapy (PDT) induces tumor cell necrosis and/or apoptosis by producing reactive oxygen species through activated photosensitizer that accumulates specifically to the tumor. Thus, PDT has much attracted as less invasive method for treating cancer. The potential applications for fullerenes and their derivatives have increased in recent years, particularly in the fields of biology and medicine, where they can be used as DNA photo-cleaving agents, anti-HIV protease inhibitors, antibacterial agents and photosensitizers for photodynamic therapy. Fullerenes are suitable for application as photosensitizer because they are efficient visible-light triplet-sensitizers and their ability to photoproduce singlet oxygen (1O2) is considerable. Although carbohydrates play essential roles in biological systems, their usage in fullerene-based PDT has remained virtually unexplored; this is essentially true of fullerene in which an intact carbohydrate moiety is connected to fullerene through an appropriate linker. We previously reported that sugar-pendant C60 derivatives prepared from carbohydrate linked azides, having 1O2 producing ability in DMSO under laser irradiation (355 nm) proved by the direct observation of 1O2 emission at 1270 nm (2). The cytotoxicity of PDT was studied in several cancer cell lines cultured with D-glucose residue pendant fullerene and a maltohexaose residue pendant fullerene (3). These glycoconjugated fullerenes induced significant cytotoxicity against cancer cells. In contrast, PDT with these compunds exhibited no significant cytotoxicity against normal fibroblasts, indicating that PDT with these compounds targeted cancer cells. Ideally, PDT-induced tumour destruction should occur without damage to adjacent normal organs. Therefore, it can be expected to design high functional glycoconjugated fullerene. Here, we wish to report on the synthesis of a novel D-glucose pendant C60 compounds derived from D-glucose linked amine, photocytotoxicity against HeLa cells and unprecedented photophysical processes together with previously prepared D-glucose pendant azafulleroids (2).
37th Congress of IUPS (Birmingham, UK) (2013) Proc 37th IUPS, PCA233
Poster Communications: Photocytotoxicity and excited-state properties of glycoconjugated C60 derivatives
S. Yano1,2, M. Naemura2, A. Toshimitsu2, M. Akiyama1, A. Ikeda1, J. Kikuchi1, A. Narumi3, K. Ohkubo4, S. Fukuzumi4, M. Gottschaldt5, U. Schubert5
1. Graduate School of Material Science, Nara Institute of Science and Technology, Ikoma, Japan. 2. Office of Society-Academia Collaboration for Innovation, Kyoto University, Kyoto, Japan. 3. Department of Polymer Science and Engineering, Yamagata University, Yonezawa, Japan. 4. Department of Material and Life Science, Osaka University, Osaka, Japan. 5. Laboratory for Organic and Macromolecular Chemistry, Friedrich-Schiller-University Jena, Jena, Germany.
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Where applicable, experiments conform with Society ethical requirements.