Diazepinoporphyrazines Containing Peripheral Styryl Substituents and Their Promising Nanomolar Photodynamic Activity against Oral Cancer Cells in Liposomal Formulations |
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| Authors: | Jaroslaw Piskorz Prof Krystyna Konopka Prof Nejat Düzgüne? Prof Zofia Gdaniec Prof Jadwiga Mielcarek Dr Tomasz Goslinski |
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| Affiliation: | 1. Department of Inorganic & Analytical Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6, 60‐780 Poznan (Poland);2. Department of Biomedical Sciences, University of the Pacific, Arthur A. Dugoni School of Dentistry, 2155 Webster Street, San Francisco, CA 94115 (USA);3. Institute of Bioorganic Chemistry, Polish Academy of Sciences, Z. Noskowskiego 12, Poznan (Poland);4. Department of Chemical Technology of Drugs, Poznan University of Medical Sciences, Grunwaldzka 6, 60‐780 Poznan (Poland) |
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| 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). |
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| Keywords: | antitumor agents diazepines liposomes photodynamic therapy porphyrazines |
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