Improved Stability and Photodynamic Activity of Water-Soluble 5,15-Diazaporphyrins Incorporated in β-(1,3-1,6)-d-Glucan with On-Off Switch

Shodai Hino; Shuhei Satake; Hideyuki Shinmori; Shigeki Kawabata; Kazuya Koumoto; Toshio Suzuki; Takeshi Nagasaki; Kouta Sugikawa; Riku Kawasaki; Atsushi Ikeda

doi:10.1002/asia.201901582

Improved Stability and Photodynamic Activity of Water-Soluble 5,15-Diazaporphyrins Incorporated in β-(1,3-1,6)-d-Glucan with On-Off Switch

Chem Asian J. 2020 Feb 3;15(3):365-370. doi: 10.1002/asia.201901582. Epub 2019 Dec 30.

Authors

Affiliations

¹ Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, 1-4-1 Kagamiyama, Higashi-Hiroshima, Hiroshima, 739-8527, Japan.
² Department of Biotechnology, Faculty of Life and Environmental Sciences, Graduate Faculty of Interdisciplinary Research, University of Yamanashi, 4-4-37 Takeda, Kofu, 400-8510, Japan.
³ Department of Liberal Arts and Sciences, Faculty of Engineering, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama, 939-0398, Japan.
⁴ Department of Nanobiochemistry, Frontiers of Innovative Research in Science and Technology (FIRST), Konan University, 7-1-20 Minatojima-Minamimachi, Kobe, Hyogo, 650-0047, Japan.
⁵ Department of Applied Chemistry and Bioengineering, Graduate School of Engineering, Osaka City University, 3-3-138 Sugimoto, Sumiyoshi-ku, Osaka, 558-8585, Japan.

PMID: 31828944
DOI: 10.1002/asia.201901582

Abstract

5,15-Diazaporphyrins, which have a large absorption at wavelengths over 600 nm, were dissolved in water by complex formation with β-(1,3-1,6)-d-glucans. Aqueous solutions of these complexes were relatively stable compared with their trimethyl-β-cyclodextrin-complexed analogues. β-Glucan-complexed diazaporphyrins showed quenched fluorescence and had low singlet-oxygen-generation abilities owing to random self-aggregation. However, external stimuli, such as the presence of liposomes or intracellular uptake, restored the fluorescence and singlet-oxygen-generation abilities of β-glucan-complexed diazaporphyrins. Consequently, β-glucan-complexed diazaporphyrins showed very high photodynamic activities toward HeLa cells.

Keywords: aggregation; fluorescent probes; host-guest systems; polysaccharide; porphyrinoids.