Physicochemical properties of liposome-incorporated 2-(morpholin-4-yl)ethoxy phthalocyanines and their photodynamic activity against oral cancer cells

ORCiD

Nejat Düzgüneş: 0000-0001-6159-1391

Department

Biomedical Sciences

Document Type

Article

Publication Title

Journal of Photochemistry and Photobiology A: Chemistry

ISSN

1010-6030

Volume

353

DOI

10.1016/j.jphotochem.2017.12.005

First Page

445

Last Page

457

Publication Date

2-15-2018

Abstract

Three 2-(morpholin-4-yl)ethoxy-substituted phthalocyanines with zinc(II) or magnesium(II) ion in the core were subjected to optical and photochemical studies, and their photodynamic activity against oral cancer cell lines was evaluated. Phthalocyanine derivatives were studied both as free compounds and after incorporation into liposomes used as drug delivery vehicles. The introduction of electron-donating 2-(morpholin-4-yl)ethoxy groups in non-peripheral positions significantly affected physicochemical and optical properties of the phthalocyanines. The increased number of substituents led to increased hydrophilicity, decreased tendency to aggregate, and a larger shift of the phthalocyanine Q band toward the red region of the spectra. The incorporation of the hydrophobic zinc(II) phthalocyanine derivative possessing two 2-(morpholin-4-yl)ethoxy substituents into liposomes triggered most pronounced changes in its physicochemical properties compared to octasubstituted compounds. The disubstituted derivative expressed a promising biological effect against oral squamous cell carcinoma with IC50 values of 22 nM and 29 nM for the free and encapsulated compound, respectively. Our results indicate that liposomes can be used as a drug delivery vehicle for hydrophobic phthalocyanines in further biological studies.

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