Water-Soluble Rotaxane-Type Porphyrin Dyes as a Highly Membrane-Permeable and Durable Photosensitizer Suitable for Photodynamic Therapy

被引：3

作者：

Ohishi, Yuki ^{[1
]}

Ichikawa, Taiki ^{[1
]}

Yokoyama, Satoru ^{[1
]}

Yamashita, Juri ^{[2
]}

Iwamura, Munetaka ^{[2
]}

Nozaki, Koichi ^{[2
]}

Zhou, Yue ^{[1
]}

Chiba, Junya ^{[1
]}

Inouye, Masahiko ^{[1
]}

机构：

[1] Univ Toyama, Grad Sch Pharmaceut Sci, Toyama 9300194, Japan

[2] Univ Toyama, Grad Sch Sci & Engn, Toyama 9308555, Japan

来源：

ACS APPLIED BIO MATERIALS | 2024年 / 7卷 / 10期

关键词：

photodynamic therapy; photosensitizer; rotaxane; porphyrin; cyclodextrin; COOPERATIVE CAPTURE SYNTHESIS; CYCLODEXTRINS; FLUORESCENCE; INCLUSION; COMPLEXES; DESIGN;

D O I：

10.1021/acsabm.4c00844

中图分类号：

TB3 [工程材料学];

学科分类号：

0805 ; 080502 ;

摘要：

Porphyrins have emerged as highly effective photosensitizers in the field of photodynamic therapy (PDT) because of their high singlet oxygen generation efficiency. However, most porphyrin derivatives do not have adequate water solubility and cell membrane permeability suitable for use in PDT. In addition, they frequently suffer from low durability under photoirradiation. Here, we propose rotaxane-type photosensitizers, in which a porphyrin axle is irreversibly encapsulated within cyclodextrins (CDs), to overcome the drawbacks of porphyrins for PDT. The rotaxane-type photosensitizers were synthesized in high yields by employing a cooperative capture strategy. The CD derivatives worked as a transparent shell to impart a porphyrin axle not only with water solubility but also with photostability. These rotaxanes showed higher cell membrane permeability and photoinduced cytotoxic abilities than talaporfin sodium, presently used as a clinical photosensitizer. The rotaxane-based photosensitizer could have potential for being ideal PDT drugs.

引用

页码：6656 / 6664

页数：9

共 39 条

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