A silyl porphyrin derivative conjugated with 6-deoxy-6-sulfo-α-d-glucopyranose functions as an efficient photosensitizer for photodynamic therapy

Hiroaki Horiuchi; Kota Nishikawa; Nozomi Ishii; Koki Kano; Shunsuke Shinada; Nene Osawa; Aoi Horikoshi; Toshitada Yoshihara; Fumio Sugawara; Kengo Sakaguchi; Tetsuo Okustu; Shinji Katsura; Ichiro Matsuo; Masahiko Oshige

doi:10.1016/j.pdpdt.2023.103898

A silyl porphyrin derivative conjugated with 6-deoxy-6-sulfo-α-d-glucopyranose functions as an efficient photosensitizer for photodynamic therapy

Photodiagnosis Photodyn Ther. 2024 Feb:45:103898. doi: 10.1016/j.pdpdt.2023.103898. Epub 2023 Nov 24.

Authors

Affiliations

¹ Division of Molecular Science, Graduate School of Science and Technology, Gunma University, Kiryu, Gunma 376-8515, Japan. Electronic address: [email protected].
² Division of Molecular Science, Graduate School of Science and Technology, Gunma University, Kiryu, Gunma 376-8515, Japan.
³ Department of Environmental Engineering Science, Graduate School of Science and Technology, Gunma University, Kiryu, Gunma 376-8515, Japan.
⁴ Department of Applied Biological Science, Faculty of Science and Technology, Tokyo University of Science, Noda, Chiba 278-8510, Japan.
⁵ Department of Environmental Engineering Science, Graduate School of Science and Technology, Gunma University, Kiryu, Gunma 376-8515, Japan; Gunma University Center for Food Science and Wellness (GUCFW), Maebashi, Gunma 371-8510, Japan.
⁶ Department of Environmental Engineering Science, Graduate School of Science and Technology, Gunma University, Kiryu, Gunma 376-8515, Japan; Gunma University Center for Food Science and Wellness (GUCFW), Maebashi, Gunma 371-8510, Japan. Electronic address: [email protected].

PMID: 38008301
DOI: 10.1016/j.pdpdt.2023.103898

Abstract

We synthesized a new silyl porphyrin derivative conjugated with 6-deoxy-6-sulfo-α-d-glucopyranose (SGlc). Conjugation with SGlc improved A549 cellular uptake without significant changes in the photophysical and photochemical properties and subcellular localization. This improved cellular uptake led to enhanced photodynamic activity. Furthermore, conjugation with SGlc suppressed dark toxicity. These advantages were not observed for a conjugate with a glucose molecule. These results indicated that the conjugation with SGlc is a promising strategy for enhancing photodynamic efficacy.

Keywords: 6-deoxy-6-sulfo-α-D-glucopyranose; Photodynamic therapy; Photosensitizer; Silyl porphyrin.

MeSH terms

A549 Cells
Glucose
Humans
Photochemotherapy* / methods
Photosensitizing Agents / pharmacology
Porphyrins* / pharmacology

Substances

Photosensitizing Agents
Glucose
Porphyrins