Extension of π-system of silylated porphyrin derivative for photodynamic therapy

Extension of π-system of silylated porphyrin derivative for photodynamic therapy

[Display omitted] •Silyl-substituted tetrabenzoporphyrin was newly synthesized.•The photodynamic activity was enhanced by the extension of π-conjugated system.•The effect of the extension of π- conjugated system and silylation were clarified. A silyl-substituted tetrabenzoporphyrin derivative has be...

Full description

Saved in:
Bibliographic Details
Published in:Journal of photochemistry and photobiology. A, Chemistry. Vol. 339; pp. 19 - 24
Main Authors: Horiuchi, Hiroaki, Sakai, Asumi, Akiyama, Shingo, Ikeda, Remi, Ito, Satoshi, Furuya, Masaru, Gomibuchi, Yuta, Ichikawa, Muneki, Yoshihara, Toshitada, Tobita, Seiji, Okutsu, Tetsuo
Format: Journal Article
Language:English
Published: Lausanne Elsevier B.V 15-04-2017
Elsevier BV
Subjects:
Absorption
Absorption spectra
Absorptivity
Cancer
Efficiency
Electromagnetic absorption
Optical properties
Oxygen
Photochemistry
Photodynamic therapy
Photosensitization
Silyl
Singlet oxygen
Tetrabenzoporphyrin
π-system
π-system
Photodynamic therapy
Silyl
Tetrabenzoporphyrin
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:[Display omitted] •Silyl-substituted tetrabenzoporphyrin was newly synthesized.•The photodynamic activity was enhanced by the extension of π-conjugated system.•The effect of the extension of π- conjugated system and silylation were clarified. A silyl-substituted tetrabenzoporphyrin derivative has been designed to improve the light absorption efficiency of the corresponding silyl-substituted porphyrin derivative via small chemical modifications. By extension of the π-conjugated system of the porphyrin derivative, its UV–vis absorption band was red-shifted and its molar absorption coefficient was increased. Although the extension of the π-conjugated system of the porphyrin derivative led to slight decreases in the quantum yield of singlet oxygen photosensitization and cellular uptake efficiency, the photodynamic activity against HeLa cells was increased 12-fold. The efficiency of the photosensitization of singlet oxygen in HeLa cells was estimated and the enhancement in photodynamic activity was mainly explained on the basis of the increase in light absorption efficiency. The effects of silylation on the photodynamic properties of tetrabenzoporphyrin derivatives have also been studied. Silylation increased cellular uptake efficiency for HeLa cells, although the UV–vis absorption properties and quantum yield of singlet oxygen photosensitization were almost independent of silylation. This increase in cellular uptake efficiency led to an improvement in photodynamic activity. By the combination of silylation and extension of the π-conjugated system of a porphyrin derivative, an efficient photosensitizer has been developed.
ISSN:1010-6030
1873-2666
DOI:10.1016/j.jphotochem.2017.02.015