Diazepino-porphyrazines containing peripheral styryl substituents and their promising nanomolar photodynamic activity against oral cancer cells in liposomal formulations

ORCiD

Nejat Düzgüneş: 0000-0001-6159-1391

Department

Biomedical Sciences

Document Type

Article

Publication Title

ChemMedChem

ISSN

1860-7179

Volume

9

Issue

8

DOI

10.1002/cmdc.201402085

First Page

1775

Last Page

1782

Publication Date

1-1-2014

Abstract

The photochemical properties and photodynamic activity of three porphyrazines (Pzs) containing annulated diazepine rings, including novel demetalated porphyrazine-possessing bis(styryl)diazepine moieties were investigated. The porphyrazines were evaluated in terms of their electronic absorption and emission properties, their tendency to undergo aggregation and photodegradation, as well as their singlet oxygen generation efficiency. The in vitro photodynamic activity of the porphyrazines and their liposomal formulations were examined by using two oral squamous cell carcinoma cell lines. Magnesium(II) tribenzodiazepinoporphyrazine (1) revealed the highest phototoxic effect in both cell lines used, H413 and HSC-3. Encapsulation of Pz 1 into L-α-phosphatidyl-d,l-glycerol:1-palmitoyl-2-oleoyl-sn-glycero-3- phosphocholine liposomes resulted in a nearly threefold increase in photocytotoxicity relative to that of the solution of Pz 1 (IC50 values of 45 and 129 nM, respectively). © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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