H2O2-responsive fluorescent single-molecule conjugated polymers and micelles, preparation methods and applications

A molecular conjugation, H2O2 technology, applied in the field of biomedicine, can solve the problems of photobleaching concentration-dependent data distortion, affecting probe sensitivity, etc., and achieve the effect of excellent photostability

Active Publication Date: 2018-05-04
SHANGHAI JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The present invention provides a H 2 o 2 Responsive fluorescent single-molecule conjugated polymers and their micelles to address the traditional small-molecule "fluorescence on-off" type H in the prior art 2 o 2 Data distortion caused by the probe itself due to severe photobleaching, high concentration dependence and equipment factors (illumination stability), ultimately affecting technical issues such as probe sensitivity

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  • H2O2-responsive fluorescent single-molecule conjugated polymers and micelles, preparation methods and applications
  • H2O2-responsive fluorescent single-molecule conjugated polymers and micelles, preparation methods and applications
  • H2O2-responsive fluorescent single-molecule conjugated polymers and micelles, preparation methods and applications

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preparation example Construction

[0057] The present invention provides a H 2 o 2 Responsive fluorescent single-molecule conjugated polymers and micelles thereof, their preparation methods and applications, in particular, can be used to distinguish tumor cells from normal cells. The fluorescent unimolecular conjugated polymer of the present invention comprises a hydrophobic hyperbranched conjugated polymer core and a hydrophilic polymer arm, and one of the hydrophobic hyperbranched conjugated polymer core and the hydrophilic polymer arm is Between by using hydrogen peroxide (H 2 o 2 ) of the corresponding boronate linkage.

[0058] In particular, when used to distinguish tumor cells from normal cells, the fluorescent single-molecule conjugated polymer micelles of the present invention can specifically target only H in tumor cells. 2 o 2 In response, the hydrophilic polymer arm of the fluorescent single-molecule conjugated polymer is broken, and the hydrophobic hyperbranched conjugated polymer core is aggr...

Embodiment 1

[0062] H in this example 2 o 2 The preparation method of the corresponding fluorescent unimolecular conjugated polymer and micelles thereof comprises the following steps:

[0063] (1) Preparation of intermediates:

[0064] Such as figure 1 As shown, the FRET donor monomer 9,9-di-n-hexyl-2,7-diboronic acid fluorene (1.05 mmol), the FRET donor monomer 9,9-di-n-hexyl-2,7-dibromofluorene ( 0.85 mmol), FRET acceptor monomer 4,7-dibromo-2,1,3-benzothiadiazole (0.1 mmol), branched monomer 1,3,5-tribromobenzene (0.1 mmol), Na 2 CO 3 (2 M, 9.5 mL, 19.0 mmol) and 20 mL of toluene were added to the reactor, under nitrogen atmosphere, the catalyst Pd (PPh 3 ) 4 (28.9 mg, 0.025 mmol), stirred and refluxed at 120°C for 3 days to obtain hyperbranched conjugated polymer 1;

[0065] Continue to add additional FRET donor monomer 9,9-di-n-hexyl-2,7-diboronic acid fluorene (monomerA, 2.0 mmol) as a capping agent and catalyst Pd(PPh 3 ) 4 (29 mg), the reaction mixture was stirred and r...

Embodiment 2

[0083] H in this example 2 o 2 The preparation method of the corresponding fluorescent unimolecular conjugated polymer and micelles thereof comprises the following steps:

[0084] (1) if figure 1 As shown, the FRET donor monomer 9,9-di-n-octyl-2,7-diboronic acid fluorene (1.05 mmol), the FRET donor monomer 9,9-di-n-octyl-2,7-dibromo Fluorene (0.85 mmol), FRET acceptor monomer 4,7-dibromo-2,1,3-benzothiadiazole (0.1 mmol), branched monomer 1,3,5-tribromobenzene (0.1 mmol ), Na 2 CO 3 (2 M, 9.5 mL, 19.0 mmol), and 20 mL of toluene were added to the reactor, under nitrogen atmosphere, the catalyst Pd(PPh 3 ) 4 (28.9 mg, 0.025 mmol), stirred and refluxed at 120°C for 3 days; continued to add 9,9-di-n-octyl-2,7-diboronic acid fluorene (monomer A, 2.0 mmol) and catalyst Pd( PPh 3 ) 4 (29 mg), the reaction mixture was stirred and refluxed at 120°C for 2 days, the reaction was terminated, the insoluble matter was removed by filtration, and the solvent was removed to obtain ...

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Abstract

The invention relates to the technical field of biomedicine, in particular to a hydrogen peroxide (H2O2)-responsive fluorescent single-molecule conjugated polymer micelle that can be used to identify tumor cells and normal cells, as well as its preparation method and application. The fluorescent unimolecular conjugated polymer in the present invention comprises a hydrophobic hyperbranched conjugated polymer core and a hydrophilic polymer arm, and the hydrophobic hyperbranched conjugated polymer core and a hydrophilic polymer arm They are linked by boronate bonds that respond to H2O2. The micelle solution formed by the assembly of the fluorescent single-molecule conjugated polymer of the present invention can specifically only respond to H2O2 in tumor cells and undergo color changes. Intracellular H2O2 has fluorescent imaging with different colors, which can achieve the purpose of distinguishing tumor cells from normal cells.

Description

technical field [0001] The invention relates to the technical field of biomedicine, in particular to a H 2 o 2 Responsive fluorescent single-molecule conjugated polymer and micelles, preparation method and application, the fluorescent single-molecule conjugated polymer micelles can be used to distinguish tumor cells and normal cells. Background technique [0002] In recent years, cancer-related molecular imaging has played an increasingly important role in the diagnosis and treatment of cancer. h 2 o 2 As a cell-transduced second messenger, it is involved in the regulation of various physiological processes. Any H caused by environmental stress or genetic mutation 2 o 2 The abnormal production and accumulation of the human body will lead to some diseases, including cancer, aging, cardiovascular disease, Alzheimer's disease, Parkinson's disease and other diseases. If intracellular H 2 o 2 Detection and imaging will be of great significance to disease diagnosis, preve...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K49/00C08G83/00C09K11/06
Inventor 朱新远黄玉
Owner SHANGHAI JIAOTONG UNIV
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