Synthesis, characterization, photochemical properties and cytotoxicity of the novel porphyrazine functionalized with nitroimidazolylbutylsulfanyl groups

A novel porphyrazine analog possessing nitroimidazolylbutylsulfanyl groups was synthesized and characterized using UV–Vis, IR, MS MALDI and various NMR techniques. In addition, a computational model following the Density Functional Theory method (DFT) was applied to analyze the FT IR spectrum. Potential photosensitizing activity of the novel porphyrazine was evaluated by measuring its ability to generate singlet oxygen (ΦΔ), which was found to reach the value of 0.045 in DMF, and 0.035 in DMSO. A lower value of singlet oxygen generation in DMSO may result from the increased tendency to aggregate, which was studied in the UV–Vis and it was found to be stronger in DMSO than in DMF solutions. The investigation indicated no release of nitric oxide (NO) from porphyrazine functionalized with nitroimidazolylbutylsulfanyl groups. In vitro studies of the new compound were carried out to investigate photosensitizer-induced photocytotoxicity on two prostate human cancer cell lines, LNCaP, PC3, and one melanoma derived cell line, MeWo.

Graphical abstractA novel porphyrazine analogue possessing nitroimidazolylbutylsulfanyl groups was synthesized and characterized using UV–Vis, IR, MS MALDI, NMR techniques and the DFT method. Photosensitizing activity was evaluated by measuring its ability to generate singlet oxygen (ΦΔ) and photosensitizer-induced photocytotoxicity on two prostate human cancer and one melanoma derived cell lines.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Porphyrazine possessing nitroimidazolylbutylsulfanyl groups was synthesized. ► Potential photosensitizing activity of the novel porphyrazine was evaluated. ► Photocytotoxicity induced by porphyrazine was investigated in vitro.