C-60 Fullerene with Tetraethylene Glycols as a Well-defined Soluble Building Block and Saccharide-conjugation Producing PDT Photosensitizer

Narumi A; Nakazawa T; Shinohara K; Kato H; Iwaki Y; Okimoto H; Kikuchi M; Kawaguchi S; Hino S; Ikeda A; Shaykoon MSA; Shen XD; Duan Q; Kakuchi T; Yasuhara K; Nomoto A; Mikata Y; Yano S

Chemistry Letters, Vol.48, No.10, 1209-1212, 2019

DOI10.1246/cl.190492 Export Citation

C-60 Fullerene with Tetraethylene Glycols as a Well-defined Soluble Building Block and Saccharide-conjugation Producing PDT Photosensitizer

Narumi A, Nakazawa T, Shinohara K, Kato H, Iwaki Y, Okimoto H, Kikuchi M, Kawaguchi S, Hino S, Ikeda A, Shaykoon MSA, Shen XD, Duan Q, Kakuchi T, Yasuhara K, Nomoto A, Mikata Y, Yano S

Tetraethylene glycol (TEG)-conjugated (C-60-I-h)[5,6]fullerene (TEG-C-60) was synthesized as a soluble molecular building block generating C-60-based conjugates with advanced properties. The improved solubility allowed the glycosylation reaction with TEG-C-60 using a Lewis acid in chloroform at low temperature. The resultant glycoconjugated TEG-C-60 was characterized in terms of water solubility, ability to generate reactive oxygen species (ROS), and photodynamic activity.

Keywords:Fullerene building block for organic synthesis;Glycosylation reaction;PDT photosensitizer