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Preparation method and application of bifunctional fluorescent probe based on oligonucleotide amphiphilic temperature-sensitive block polymer

A technology of block polymer and oligonucleotide, applied in the application field of Hg2+ ion and cysteine ​​dual function detection, can solve the problems of poor recovery, low detection sensitivity, single response, etc. Improve sensitivity and selectivity

Active Publication Date: 2019-11-22
JIANGSU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, the existing fluorescence-based chemical sensors based on organic small molecules, which are currently used in related fluorescence detection technologies, usually have disadvantages such as poor water solubility, low detection sensitivity, poor recyclability, and single response, which limit their potential applications in biological systems.

Method used

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  • Preparation method and application of bifunctional fluorescent probe based on oligonucleotide amphiphilic temperature-sensitive block polymer
  • Preparation method and application of bifunctional fluorescent probe based on oligonucleotide amphiphilic temperature-sensitive block polymer
  • Preparation method and application of bifunctional fluorescent probe based on oligonucleotide amphiphilic temperature-sensitive block polymer

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] (1) Preparation of HBMA monomer

[0052] 4-Hydroxybenzaldehyde (1.96 g, 16 mmol) and triethylamine (1.62 g, 16 mmol) were dissolved in anhydrous CH 2 Cl 2 (30mL). In an ice-water bath at 0°C, methacryloyl chloride (2 g, 19.2 mmol) was added dropwise, and the mixture was stirred overnight. The reaction solution was then washed several times with sodium bicarbonate solution. Subsequently, the organic layer was dried over anhydrous sodium sulfate. Under reduced pressure, the organic solvent was evaporated to obtain the crude product. In ethanol solution, a white solid (HBMA monomer) was obtained by recrystallization.

[0053] (2) Preparation of benzyl trithiocarbonate (BTPA)

[0054] 3-Mercaptopropionic acid (2.5mL, 23mmol) was added dropwise to an aqueous solution of potassium hydroxide (1.95mol / L, 32mL), and carbon disulfide (4.5g, 59mmol) was added dropwise with stirring. After reacting at room temperature for 5 hours, benzyl bromide (6 g, 35 mmol) was added to t...

Embodiment 2

[0071] Thermosensitive Block Polymer Fluorescent Probe PEG 113 -b-P(NIPAM-co-HBMA) m -Study on temperature-sensitive performance of P1

[0072] (1) To study the effect of temperature on the morphology of polymer assemblies, the results are as follows Figure 6 shown. exist Figure 6 (a), PEG 113 -b-P(NIPAM-co-HBMA) m The aqueous solution of -P1 exists in the state of single-chain dissolution at 25°C; Figure 6 In (b), when the temperature reaches 40 °C, the polymer self-assembles to form spherical micelles with P(NIPAM-co-HBMA)-P1 as the core and PEG as the shell.

[0073] (2) Exploring the polymer PEG by dynamic laser light scattering (DLS) 113 -b-P(NIPAM-co-HBMA) m - Temperature-induced behavior of P1. Dynamic laser light scattering such as Figure 7 As shown, dynamic laser light scattering is shown in the figure, PEG 113 -b-P(NIPAM-co-HBMA) m When the aqueous solution of -P1 is at 25°C, its particle size is 10.1 nm, and its polydispersity coefficient is 0.289. ...

Embodiment 3

[0075] Thermosensitive Polymer Fluorescent Probe PEG 113 -b-P(NIPAM-co-HBMA) m -Analytical research on cloud point of P1

[0076] Prepare the probe solution to a concentration of 0.002g / mL, 0.005g / mL, 0.008g / mL, 0.01g / mL, 0.02g / mL, 0.03g / mL, 0.04g / mL, 0.05g / mL, 0.06g / mL, 0.07g / mL, 0.08g / mL, 0.09g / mL, 0.10g / mL solutions. Such as Figure 8 As shown, different concentrations of thermosensitive polymer fluorescent probe PEG 113 -b-P(NIPAM-co-HBMA) m - Cloud point of P1. It can be drawn from the figure that the cloud point will decrease with the increase of the concentration of the temperature-sensitive polymer fluorescent probe solution. When the concentration of the thermosensitive polymer fluorescent probe was increased to 0.10g / mL, the cloud point no longer decreased. Therefore, the lowest critical point temperature (LCST) of the temperature-sensitive polymer fluorescent probe solution is 27.6°C, that is, when the temperature is higher than 27.6°C, PEG 113 -b-P(NIPAM-c...

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Abstract

The invention aims to provide a preparation method of a bifunctional fluorescent probe based on an oligonucleotide amphiphilic temperature-sensitive block polymer and an application thereof in bifunctional detection of Hg<2+> ions and cysteine (Cys) in the environment. The preparation method comprises the following steps: firstly, preparing an HBMA monomer; then performing a reaction with a macromolecular chain transfer agent of methoxypolyethylene glycol and N-isopropylacrylamide to synthesize the temperature-sensitive block polymer, which is narrow in distribution width index, controllable in molecular weight and appropriate in low critical phase transition temperature; and finally combining the block polymer with a fluorophore-labeled nucleic acid aptamer (P1) to form the fluorescent probe. The bifunctional fluorescent probe based on an oligonucleotide amphiphilic temperature-sensitive block polymer can be specifically combined with cysteine (Cys) after specifically detecting Hg<2+>ions so as to achieve the purpose of bifunctional detection. The method has the characteristics of good selectivity and sensitivity, convenience in operation, mild detection conditions, easiness in polymer recycling and the like.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes and preparation methods thereof, and relates to the use of oligonucleotide amphiphilic temperature-sensitive block polymers as fluorescent probes in the environment against Hg 2+ Application of ion and cysteine ​​(Cys) dual function detection. Background technique [0002] Mercury is a highly toxic global environmental pollutant, especially its high mobility, persistence, methylation, bioaccumulation, and food chain amplification. Human, animal and plant health are also a great threat. Studies have confirmed that even low levels of mercury in the body can cause serious damage to the prenatal brain, lungs, heart, kidneys, central nervous system and immune system. Therefore, the detection of trace mercury becomes critical. [0003] L-cysteine ​​(Cys) is an amino acid containing a sulfhydryl group (-SH), which is one of the essential amino acids for the human body. If Cys is lacking in ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F293/00C08F220/54C08F220/28C08F8/40C09K11/06G01N21/64G05D1/02
CPCC08F8/40C08F220/28C08F220/54C08F293/005C09K11/06C09K2211/1088G01N21/6428G01N21/643G01N21/6486G01N2021/6432G05D1/021
Inventor 王宇练冬生王蕾刘园园刘永冠李文轩王赟倪良
Owner JIANGSU UNIV
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