Effect of meso Positioned Substituents on the Stability and Photodynamic Activity of Lipid‐Membrane‐Incorporated Porphyrin Derivatives

In this study we prepared aqueous solutions of lipid‐membrane incorporated tetraarylporphyrins and tetrapyridylporphyrin (LMIPors) by the injection method using dimethyl sulfoxide. The porphyrins with proton‐donor groups at the meso position afforded stable aqueous solutions of LMIPors. However, alt...

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Bibliographic Details
Published in:ChemMedChem 2022-05, Vol.17 (9), p.e202200070-n/a
Main Authors: Nishimura, Kotaro, Shimada, Risako, Yamana, Keita, Kawasaki, Riku, Nakaya, Toshimi, Ikeda, Atsushi
Format: Article
Language:English
Subjects:
Aqueous solutions
Dimethyl sulfoxide
drug delivery
Lipid membranes
Lipids
Liposomes
Membranes
photodynamic therapy
photosensitizers
Photosensitizing Agents - pharmacology
porphyrinoids
Porphyrins
Porphyrins - pharmacology
Water
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Summary:In this study we prepared aqueous solutions of lipid‐membrane incorporated tetraarylporphyrins and tetrapyridylporphyrin (LMIPors) by the injection method using dimethyl sulfoxide. The porphyrins with proton‐donor groups at the meso position afforded stable aqueous solutions of LMIPors. However, although tetrakis(carboxyphenyl)porphyrin was scarcely incorporated in lipid membranes, it was soluble in water. Among these LMIPors, the photodynamic activity of tetrakis(hydroxyphenyl)porphyrin was higher than that of tetrakis(aminophenyl)porphyrin. This was attributed to the self‐aggregation of a part of tetrakis(aminophenyl)porphyrin in the liposomes, which induced self‐quenching and the consequent decrease of its photodynamic activity. Aqueous solutions of lipid‐membrane‐incorporated tetrakis(hydroxyphenyl)porphyrin and tetrakis(aminophenyl)porphyrin prepared by the injection method using dimethyl sulfoxide were found to be highly stable, and the former exhibited higher photodynamic activity toward HeLa cells than did the latter.
ISSN:1860-7179
1860-7187
DOI:10.1002/cmdc.202200070