A series of pegylated cis-A2B2- or A3B-type ZnPcs , substituted on the α-positions with tri(ethylene glycol) and hydroxyl groups, were synthesized from a new bis-phthalonitrile. A clamshell-type bis-phthalocyanine was also obtained as a byproduct. The hydroxyl group of one ZnPc was alkylated with 3-dimethylaminopropyl chloride to afford a pegylated ZnPc functionalized with an amine group. All mononuclear ZnPcs were soluble in polar organic solvents, showed intense Q absorptions in DMF, and had fluorescence quantum yields in the range 0.10–0.23. The clamshell-type bis-phthalocyanine adopts mainly open shell conformations in DMF, and closed clamshell conformations in chloroform. All ZnPcs were highly phototoxic to human carcinoma HEp2 cells, particularly the amino- ZnPc mainly protonated under physiological conditions, which showed the highest phototoxicity (IC50 = 0.5 μM at 1.5 J/cm2) dark cytotoxicity (IC50 = 22 μM), in part due to its high cellular uptake. The ZnPcs localized in multiple organelles, including mitochondria, lysosomes, Golgi and ER.

中文翻译：

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α-聚乙二醇化 cis-A2B2- 和 A3B- 型 ZnPcs 的合成、光谱和细胞特性

一系列聚乙二醇化cis-A2乙2- 或一个3由一种新的双邻苯二甲腈合成了在α位被三（乙二醇）和羟基取代的B型ZnPcs。还获得了蛤壳型双酞菁作为副产物。一种 ZnPc 的羟基用 3-二甲基氨基丙基氯烷基化，得到用胺基官能化的聚乙二醇化 ZnPc。所有单核 ZnPcs 均可溶于极性有机溶剂，在 DMF 中显示出强烈的 Q 吸收，并且荧光量子产率在 0.10-0.23 范围内。蛤壳型双酞菁在DMF中主要采用开壳构象，在氯仿中采用闭合蛤壳构象。所有 ZnPc 对人肝癌 HEp2 细胞均具有高光毒性，特别是在生理条件下主要质子化的氨基-ZnPc 表现出最高的光毒性（IC50= 0.5 μM，1.5 J/cm2) 暗细胞毒性 (IC50= 22 μM），部分原因是其高细胞吸收。ZnPcs 定位于多种细胞器，包括线粒体、溶酶体、高尔基体和 ER。