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Novel hydro- and lipo-philic selenium zinc(II) phthalocyanines: Synthesis, photophysical properties and photodynamic effects on CT26 colon carcinoma cells
Dyes and Pigments ( IF 4.5 ) Pub Date : 2018-03-29 , DOI: 10.1016/j.dyepig.2018.03.067
Sergio D. Ezquerra Riega , Nicolás Chiarante , Federico Valli , Julieta Marino , Leonor P. Roguin , Josefina Awruch , María C. García Vior

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.



中文翻译:

新型亲水和亲脂性硒锌(II)酞菁类化合物:对CT26结肠癌细胞的合成,光物理性质和光动力效应

两种新型硒化锌硒酞菁类化合物的合成及光化学性质,脂溶性2,9(10),16(17),23(24)-四[[2-(2-二甲基氨基)乙基硒基]酞菁锌(II) (4)及其水溶性季铵化衍生物2,9(10),16(17),23(24)-四[[(2-三甲基铵)乙基硒基]酞菁锌四碘化锌(II)(5)。DMF中4和5的最大吸收值分别为689 nm和684 nm。此外,酞菁被发现是非常有效的单重态氧发生器与Φ的高值Δ为0.74和0.84 45在DMF中,它们在研究的辐射时间内是光稳定的。评价对CT26结肠癌细胞的光动力作用。曝光后,发现45具有细胞毒性,IC 50值分别为0.5±0.1μM和2.3±0.6μM。酞菁辐照后产生大量的活性氧将导致其对CT26结肠癌细胞的强光毒性作用。

更新日期:2018-03-29
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