BODIPY-Based Photosensitizers as Potential Anticancer and Antibacterial Agents: Role of the Positive Charge and the Heavy Atom Effect

Abstract

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 Φ_Δ 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.

Keywords: BODIPY; cancer; halogenation; photochemistry; photodynamic antimicrobial chemotherapy.