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Acta Chimica Sinica >

2014 , Vol. 72 >Issue 4: 440 - 446

DOI: https://doi.org/10.6023/A13121247

Article

Biotinylated Water-Soluble Conjugated Polymers：Synthesis and the Application in Biological Analysis

  • Liu Xingfen ,
  • Cai Xiaohui ,
  • Huang Yanqin ,
  • Shi Lin ,
  • Fan Quli ,
  • Huang Wei
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  • a Key Laboratory for Organic Electronics & Information Displays (KLOEID) and Institute of Advanced Materials (IAM), Nanjing University of Posts and Telecommunications, Nanjing 210023;
    b Jiangsu-Singapore Joint Research Center for Organic/Bio-Electronics & Information Displays and Institute of Advanced Materials, Nanjing Tech University, Nanjing 211816)

Received date: 2013-12-20

  Online published: 2014-02-14

Supported by

Project supported by the National Basic Research Program of China (Nos. 2009CB930601, 2012CB933301, 2012CB723402), the National Natural Science Foundation of China (Nos. 21005040, 51073078, 51173080), the Ministry of Education of China (No. IRT1148), the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) and the Program of Scientific Innovation Research of College Graduate in Jiangsu Province (CXLX12_0468).

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Abstract

Conjugated polymers with good photostability, high absorption coefficients and quantum yields have attracted great interest in biological analysis, molecular electronics and organic electronics. Biofunctional conjugated polymers have many advantages in bioanalysis, such as high selectivity and excellent tumor targeting capacity. Herein, a biotinylated water-soluble conjugated polyfluorene derivative (PFPNBr-biotin) with blue fluorescence emission characteristic was synthesized via Sonogashira coupling reaction by using Pd(PPh3)4/CuI as catalysts. The molecular structure of compounds, neutral polymer and cationic polymer were characterized by nuclear magnetic resonance (NMR) and Fourier transform infrared spectroscopy (FT-IR); molecule weight and distribution of polymers were characterized by gel permeation chromatography (GPC) and other methods. The photophysical properties of the PFPNBr-biotin in mixed solvent systems with different ratio of methanol to water were studied by monitoring its fluorescence spectra. The results demonstrate an increased fluorescence intensity of PFPNBr-biotin with the increase of methanol. Changes in the photophysical properties of PFPNBr-biotin with the increasing polymer concentration were investigated by measuring UV-vis absorbance and fluorescence spectra. Some aggregates may form when the concentration of polymer is more than 400 μmol·L-1, which corresponding to decreased UV-vis absorbance and fluorescence emission. Optical properties of PFPNBr-biotin itself and the protein detection with PFPNBr-biotin in solutions of different pHs were studied to analyze the aggregation behavior before and after interacting with protein. Compared to the nonfunctional conjugated polymer, PFPNBr-biotin shows excellent selectivity to avidin over negative proteins such as lysozyme (Lys), immunoglobin G (IgG), hemoglobin (Hb) and bovine serum albumin (BSA). So it can be used to distinguish avidin (or strapatavidin) over many proteins just by monitoring the fluorescence change of PFPNBr-biotin. Considering the fact that biotin-avidin system has been widely used in biological analysis, we believe that this biotinylated water-soluble conjugated polymer has a potential application in detecting and labeling of biomolecules and fluorescence imaging of tumor cells.

Key words： biotin; water-soluble conjugated polymers; biofunctionalization; bioanalysis

Cite this article

Liu Xingfen , Cai Xiaohui , Huang Yanqin , Shi Lin , Fan Quli , Huang Wei . Biotinylated Water-Soluble Conjugated Polymers：Synthesis and the Application in Biological Analysis[J]. Acta Chimica Sinica, 2014 , 72(4) : 440 -446 . DOI: 10.6023/A13121247

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