摘要/Abstract
以L-天冬氨酸为原料，在体积分数为85%的磷酸催化条件下采用热缩合方法合成了聚琥珀酰亚胺大分子，用罗丹明B与乙二胺反应生成的罗丹明-乙二胺衍生物的氨基以及乙醇胺上的氨基对聚琥珀酰亚胺进行开环反应，合成了含罗丹明B基团的聚天冬酰胺大分子.通过溴化与亲核取代反应将磺胺嘧啶基团接枝于聚天冬酰胺大分子上，从而制备具有肿瘤靶向功能的水溶性聚天冬酰胺大分子荧光探针（SD-PHEA-RhB）.对所合成的荧光探针进行了核磁共振谱、红外光谱、紫外-可见光谱、凝胶渗透色谱和质谱等结构表征，进一步测试了其分子量及分布、粒径、荧光性能、体外细胞毒性与细胞摄取以及荧光成像性能.实验结果表明，所合成的聚天冬酰胺荧光成像探针具有良好的水溶性和荧光性能，对酸性环境敏感，对HepG2和HeLa细胞均具有较低的体外细胞毒性，能被HeLa肿瘤细胞选择性摄取，且能获得较好的HeLa细胞红色荧光成像.
关键词: 荧光成像, 荧光探针, 肿瘤靶向, 聚天冬酰胺, 磺胺嘧啶, 罗丹明B
Polysuccinimide (PSI) was synthesized by thermal condensation of L-aspartic acid as raw materials and phosphoric acid (85% by volume) as catalyst. The water-soluble polyaspartamide fluorescent probes (SD-PHEA-RhB) was further synthesized by ring-opening reaction between PSI with the amino groups of ethanolamine and rhodamine B (RhB) modified by ethylenediamine, and then nucleophilic substitution reaction of sulfadiazine (SD). SD-PHEA-RhB was characterized by 1H NMR, IR, UV, gel permeation chromatograph (GPC), mass spectrometry and so on. Its molecular weight and distribution, particle size, fluorescence properties, in vitro cell cytotoxicity, cellular uptake and fluorescent imaging assays were also measured. Experimental data showed that the fluorescent probe possessed good water solubility and high sensitive to the acidic conditions. Moreover, these fluorescent probes had low in vitro cytotoxicities to HepG2 and HeLa cells, high specific uptake and good red fluorescent imaging in HeLa tumor cells.
Key words: fluorescent imaging, fluorescent probe, tumor-targeting, polyaspartamide, sulfadiazine, Rhodamine B
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