Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (4): 938-943.DOI: 10.6023/cjoc201908003 Previous Articles     Next Articles


张淼a, 刘凡a, 柯希骏a, 陈思a, 鄢国平a, 张桥a, 梁淑彩b, 王玉芳a, 蒋灿a   

  1. 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 发布日期:2019-12-27
  • 通讯作者: 刘凡, 鄢国平;
  • 基金资助:

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

Zhang Miaoa, Liu Fana, Ke Xijuna, Chen Sia, Yan Guopinga, Zhang Qiaoa, Liang Shucaib, Wang Yufanga, Jiang Cana   

  1. a School of Materials Science and Engineering, Wuhan Institute of Technology, Wuhan 430205;
    b School of Pharmaceutical Sciences, Wuhan University, Wuhan 430072
  • Received:2019-08-03 Revised:2019-10-18 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).

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