Novel hydro- and lipo-philic selenium zinc(II) phthalocyanines: Synthesis, photophysical properties and photodynamic effects on CT26 colon carcinoma cells

• Published in: Dyes and pigments 2018-09, Vol.156, p.133-139
• Main Authors: Ezquerra Riega, Sergio D., Chiarante, Nicolás, Valli, Federico, Marino, Julieta, Roguin, Leonor P., Awruch, Josefina, García Vior, María C.
• Format: Article
• Language: English
• Subjects: CT26 cells; Photodynamic therapy; Selenium zinc(II) phthalocyanines; Singlet oxygen
• ISSN: 0143-7208; 1873-3743
• DOI: 10.1016/j.dyepig.2018.03.067

The synthesis and photochemical properties of two novel selenium zinc(II) phthalocyanines, a lipid-soluble 2,9(10),16(17),23(24)-tetrakis [(2-dimethylamino)ethylselanyl]phthalocyaninato zinc(II) (4) and its water-soluble quaternized derivative 2,9(10),16(17),23(24)-tetrakis [(2- trimethylammonium)ethylselanyl]phthalocyaninato zinc(II) tetraiodide (5), were investigated. Maximum absorption values were 689 nm and 684 nm for 4 and 5 in DMF, respectively. In addition, phthalocyanines were revealed to be very efficient singlet oxygen generators with high values of ΦΔ 0.74 and 0.84 for 4 and 5 in DMF, and they were photostable over the irradiation times studied. The photodynamic effect were evaluated on CT26 colon carcinoma cells. After light exposure, 4 and 5 were found to be cytotoxic, and IC50 values were 0.5 ± 0.1 μM and 2.3 ± 0.6 μM, respectively. The production of a greater amount of reactive oxygen species after phthalocyanines irradiation would be responsible for its potent phototoxic action on CT26 colon carcinoma cells. [Display omitted] •Novel hydro- and lipo-philic selenium zinc(II) phthalocyanines are synthetized.•The phthalocyanines are efficient singlet oxygen quantum yield generators.•The photodynamic effect is evaluated on murine colon carcinoma CT26 cells.•Lipophilic selenium phthalocyanine shows a higher phototoxicity (IC50 = 0.5 ± 0.1 μM).•Water soluble selenium phthalocyanine presents the highest photostability.