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Chinese Journal of Organic Chemistry >

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

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

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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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

Cite this article

Zhang Miao , Liu Fan , Ke Xijun , Chen Si , Yan Guoping , Zhang Qiao , Liang Shucai , Wang Yufang , Jiang Can . Polyaspartamide Fluorescent Probe Containing Rhodamine B and Sulfadiazine Groups for Molecular Imaging and Diagnosis[J]. Chinese Journal of Organic Chemistry, 2020 , 40(4) : 938 -943 . DOI: 10.6023/cjoc201908003

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