title: Diazepinoporphyrazines containing peripheral styryl substituents and their promising nanomolar photodynamic activity against oral cancer cells in liposomal formulations.
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).
authors.affiliation: Department of Inorganic & Analytical Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznan (Poland). piskorzj@ump.edu.pl.
authors.forename: Jaroslaw
authors.initials: J
authors.lastname: Piskorz
authors.forename: Krystyna
authors.initials: K
authors.lastname: Konopka
authors.forename: Nejat
authors.initials: N
authors.lastname: Düzgüneş
authors.forename: Zofia
authors.initials: Z
authors.lastname: Gdaniec
authors.forename: Jadwiga
authors.initials: J
authors.lastname: Mielcarek
authors.forename: Tomasz
authors.initials: T
authors.lastname: Goslinski
mesh_terms: D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D006801:Humans; D007700:Kinetics; D008081:Liposomes / Q000737:chemistry*; D009062:Mouth Neoplasms / Q000188:drug therapy; D010778:Photochemotherapy; D010782:Photolysis; D017319:Photosensitizing Agents / Q000737:chemistry* / Q000494:pharmacology* / Q000627:therapeutic use; D011166:Porphyrins / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D026082:Singlet Oxygen / Q000378:metabolism
chemical_list: D008081:Liposomes; D017319:Photosensitizing Agents; D011166:Porphyrins; D026082:Singlet Oxygen
keywords: antitumor agents; diazepines; liposomes; photodynamic therapy; porphyrazines