Synthesis, physical–chemical properties and in vitro photodynamic activity against oral cancer cells of novel porphyrazines possessing fluoroalkylthio and dietherthio substituents

Novel porphyrazines possessing fluoroalkylthio and dietherthio peripheral substituents were synthesized and tested from the peripheral substituent effects on their physical–chemical properties, including metal binding abilities and solvatochromic effects. Two porphyrazines were subjected to singlet oxygen generation measurements using 1,3-diphenylisobenzofuran as a singlet oxygen scavenger and examined in vitro towards oral cancer cells. Biological investigation performed on two human squamous carcinoma cell lines derived from the tongue (HSC-3) and from the buccal mucosa (H413) revealed moderate activity and selectivity of novel magnesium(II) porphyrazine possessing peripheral 4-fluorobutylthio substituents.

The photochemical properties and biological activity of the series of novel porphyrazines possessing fluoroalkylthio and dietherthio peripheral substituents are presented.Figure optionsDownload as PowerPoint slideHighlights
► Novel porphyrazines possessing fluoroalkylthio and dietherthio substituents were synthesized.
► Compounds were subjected to photochemical measurements.
► Biological investigation on two human squamous carcinoma cell lines was performed.