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2020 , Vol. 40 >Issue 4: 938 - 943

DOI: https://doi.org/10.6023/cjoc201908003

研究论文

含罗丹明B基团的聚天冬酰胺荧光成像探针研究

  • 张淼 ,
  • 刘凡 ,
  • 柯希骏 ,
  • 陈思 ,
  • 鄢国平 ,
  • 张桥 ,
  • 梁淑彩 ,
  • 王玉芳 ,
  • 蒋灿
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  • a 武汉工程大学材料科学与工程学院 武汉 430205;
    b 武汉大学药学院 武汉 430072

收稿日期: 2019-08-03

  修回日期: 2019-10-18

  网络出版日期: 2019-12-27

基金资助

国家重点研发计划专项（Nos.2016YFB1101302，2018YFB1105502）、武汉市"黄鹤英才计划"（创新人才）项目（No.武人才办[2017]1）、湖北省新世纪高层次人才工程人选科研项目（No.鄂人社函[2017]344）、咸宁市"南鄂英才"及创新创业项目（No.咸人组文[2019]11）、武汉工程大学科学基金（No.K201861）资助项目.

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Polyaspartamide Fluorescent Probe Containing Rhodamine B and Sulfadiazine Groups for Molecular Imaging and Diagnosis

  • Zhang Miao ,
  • Liu Fan ,
  • Ke Xijun ,
  • Chen Si ,
  • Yan Guoping ,
  • Zhang Qiao ,
  • Liang Shucai ,
  • Wang Yufang ,
  • Jiang Can
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  • a School of Materials Science and Engineering, Wuhan Institute of Technology, Wuhan 430205;
    b School of Pharmaceutical Sciences, Wuhan University, Wuhan 430072

Received date: 2019-08-03

  Revised date: 2019-10-18

  Online published: 2019-12-27

Supported by

Project supported by the National Key Research and Development Programm (Nos. 2016YFB1101302, 2018YFB1105502), the Wuhan Yellow Crane Talents Program (No.[2017]1), the Scientific Research Projects for High Level Talents in the New Century (No.[2017]344), the South Hubei Talents Project of Innovation and Entrepreneurship (No.[2019]11) and the Scientific Research Fund Project of Wuhan Institute of Technology (No. K201861).

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摘要

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

本文引用格式

张淼 , 刘凡 , 柯希骏 , 陈思 , 鄢国平 , 张桥 , 梁淑彩 , 王玉芳 , 蒋灿 . 含罗丹明B基团的聚天冬酰胺荧光成像探针研究[J]. 有机化学, 2020 , 40(4) : 938 -943 . DOI: 10.6023/cjoc201908003

Abstract

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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