Formation of Water-Soluble Complexes from Fullerene with Biocompatible Block Copolymers Bearing Pendant Glucose and Phosphorylcholine

• Published in: Langmuir Vol. 38; no. 18; pp. 5744 - 5751
• Main Authors: Kitano, Kohei, Ishihara, Kazuhiko, Yusa, Shin-ichi
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 10.05.2022
• Subjects: Fullerenes; Glucose; Methacrylates - chemistry; Phosphorylcholine - chemistry; Polymers - chemistry; Water - chemistry
• ISSN: 0743-7463; 1520-5827
• DOI: 10.1021/acs.langmuir.2c00354

Double-hydrophilic diblock copolymers, PMPC100-block-PGEMA n (M100G n ), were synthesized via reversible addition–fragmentation chain transfer radical polymerization using glycosyloxyethyl methacrylate and 2-(methacryloyloxy)­ethyl phosphorylcholine. The degree of polymerization (DP) of the poly­(2-(methacryloyloxy) ethylphosphorylcholine) (PMPC) block was 100, whereas the DPs (n) of the poly­(glycosyloxyethyl methacrylate) PGEMA block were 18, 48, and 90. Water-soluble complexes of C70/M100G n and fullerene (C70) were prepared by grinding M100G n and C70 powders in a mortar and adding phosphate-buffered saline (PBS) solution. PMPC can form a water-soluble complex with hydrophobic C70 using the same method. Therefore, the C70/M100G n complexes have a core–shell micelle-like particle structure possessing a C70/PMPC core and PGEMA shells. The maximum amounts of solubilization of C70 in PBS solutions using 2 g/L each of M100G18, M100G48, and M100G90 were 0.518, 0.358, and 0.257 g/L, respectively. The hydrodynamic radius (R h) of C70/M100G n in PBS solutions was 55–75 nm. Spherical aggregates with a similar size to the R h were observed by transmission electron microscopy. When the C70/M100G n PBS solutions were irradiated with visible light, singlet oxygen was generated from C70 in the core. It is expected that the C70/M100G n complexes can be applied to photosensitizers for photodynamic therapy treatments.