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Boron‐dipyrromethene derivatives, including cationic and iodinated analogs, were obtained and subjected to physicochemical and in vitro photodynamic activity studies. Iodinated derivatives revealed a substantial heavy atom effect manifested by a bathochromic shift of the absorption band by about 30 nm and fluorescence intensity reduced by about 30–35 times, compared to that obtained for non‐iodinated ones. In consequence, singlet oxygen generation significantly increased with ΦΔ values in the range 0.69–0.97. The in vitro photodynamic activity was evaluated on Gram‐positive Staphylococcus aureus, Gram‐negative Escherichia coli, and on human androgen‐sensitive prostate adenocarcinoma cells (LNCaP). The novel cationic, iodinated BODIPY, demonstrated the highest activity toward all studied cells. An excellent cytotoxic effect was found against LNCaP cells with an IC50 value of 19.3 nM, whereas the viability of S. aureus was reduced by >5.6 log10 at 0.25 μM concentration and by >5.3 log10 in the case of E. coli at 5 μM. Thus, this analog seems to be a very promising candidate for the application in both anticancer and antimicrobial photodynamic therapy.

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).