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H2O2-responded fluorescent single-molecule conjugated polymer and micelle, preparation method and application thereof

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

Active Publication Date: 2016-03-02
SHANGHAI JIAO TONG UNIV
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  • 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

Method used

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  • H2O2-responded fluorescent single-molecule conjugated polymer and micelle, preparation method and application thereof
  • H2O2-responded fluorescent single-molecule conjugated polymer and micelle, preparation method and application thereof
  • H2O2-responded fluorescent single-molecule conjugated polymer and micelle, preparation method and application thereof

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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 as well as 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 only target H in tumor cells. 2 o 2 In response, the hydrophilic polymer arm of the fluorescent single-molecule conjugated polymer is broken, and its hydrophobic hyperbranched conjugated polymer co...

Embodiment 1

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

[0063] (1) Preparation of intermediates:

[0064] like 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 ( 0.85mmol), FRET acceptor monomer 4,7-dibromo-2,1,3-benzothiadiazole (0.1mmol), branched monomer 1,3,5-tribromobenzene (0.1mmol), Na 2 CO 3 (2M, 9.5mL, 19.0mmol) and 20mL of toluene were added to the reactor, under nitrogen atmosphere, the catalyst Pd(PPh 3 ) 4 (28.9mg, 0.025mmol), 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 (29mg), the reaction mixture was stirred and refluxed at 120°C...

Embodiment 2

[0083] H in this example 2 o 2The 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 (1.05mmol), the FRET donor monomer 9,9-di-n-octyl-2,7-dibromo Fluorene (0.85mmol), FRET acceptor monomer 4,7-dibromo-2,1,3-benzothiadiazole (0.1mmol), branched monomer 1,3,5-tribromobenzene (0.1mmol ), Na 2 CO 3 (2M, 9.5mL, 19.0mmol), and 20mL toluene were added to the reactor, under nitrogen atmosphere, the catalyst Pd(PPh 3 ) 4 (28.9mg, 0.025mmol), stirred and refluxed at 120°C for 3 days; continued to add 9,9-dioctyl-2,7-diboronic acid fluorene (monomerA, 2.0mmol) and catalyst Pd(PPh 3 ) 4 (29mg), 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 a light yellow viscous ...

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Abstract

The invention relates to the technical field of biological medicine, and especially relates to a hydrogen peroxide (H2O2)-responded fluorescent single-molecule conjugated polymer micelle used for discriminating tumor cells and normal cells, a preparation method and an application thereof. The fluorescent single-molecule conjugated polymer comprises a hydrophobic hyper branched conjugated polymer core and a hydrophobic polymer arm, and the hydrophobic hyper branched conjugated polymer core and the hydrophobic polymer arm are connected by using a H2O2-responded borate bond. According to the invention, a micelle solution formed by assembling the fluorescent single-molecule conjugated polymer can specially generate color change according to H2O2 response in the tumor cells, the fluorescent single-molecule conjugated polymer micelle has fluorescence imaging with different colors to tumor cells and H2O2 in the normal cells, and can reach a purpose of discrimination of the tumor cells and the 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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IPC IPC(8): C08G83/00C09K11/06A61K49/00
Inventor 朱新远黄玉
Owner SHANGHAI JIAO TONG UNIV
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