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Biocompatible nanoparticles with aggregation induced emission characteristics as fluorescent bioprobes and methods of using the same for in vitro and in vivo imaging

A technology of fluorescent biological probes and aggregation-induced luminescence, which is applied in biochemical equipment and methods, measurement/inspection of microorganisms, preparations for in vivo experiments, etc., and can solve problems such as limitations of nanoparticle bioimaging and limited fluorescence intensity

Active Publication Date: 2014-06-04
THE HONG KONG UNIV OF SCI & TECH +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

As a result, the loaded dye concentration in the nanoparticles can only reach moderate levels, resulting in very limited fluorescence intensities available
Therefore, in practical applications, nanoparticles loaded with organic fluorophores are greatly limited in in vitro and in vivo bioimaging.

Method used

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  • Biocompatible nanoparticles with aggregation induced emission characteristics as fluorescent bioprobes and methods of using the same for in vitro and in vivo imaging
  • Biocompatible nanoparticles with aggregation induced emission characteristics as fluorescent bioprobes and methods of using the same for in vitro and in vivo imaging
  • Biocompatible nanoparticles with aggregation induced emission characteristics as fluorescent bioprobes and methods of using the same for in vitro and in vivo imaging

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preparation example Construction

[0154] Preparation method of nanoparticles loaded with fluorescent compounds

[0155] Another embodiment of the present invention is a method for preparing fluorescent compound-loaded nanoparticles further comprising a biocompatible polymer matrix. In another embodiment, nanoparticles loaded with fluorescent compounds are used as fluorescent bioprobes. First, prepare a solution containing an organic solvent and a fluorescent compound. The organic solvent described here is preferably a solvent with a low boiling point, such as tetrahydrofuran (THF). An aqueous solution of the biocompatible polymer is then prepared. The THF solution and the aqueous solution were mixed together and sonicated. The fluorescent compound and biocompatible polymer can then be cross-linked. However, if the biocompatible polymer is DSPE-PEG, no cross-linking is required. Finally, THF is removed to form fluorescent compound-loaded nanoparticles further comprising a biocompatible polymer matrix.

...

Embodiment 1

[0283] Synthesis of TPE-TPA-DCM

[0284] The reaction scheme for the synthesis of TPE-TPA-DCM is shown below.

[0285]

[0286] 2-(2,6-dimethyl-4H-pyran-4-ylidene) malononitrile (2) is synthesized from 2,6-dimethyl-4-pyrone (1), and the yield is 73%. (2) TPA-DCM and Br-TPA-DCM were obtained through Knoevenagel condensation reaction with TPA-containing aldehyde, and the yields were both higher than 70%. Under alkaline conditions, tetrakis(triphenylphosphine) palladium (Pd(PPh 3 ) 4 ) as a catalyst, TPE-TPA-DCM was obtained by Suzuki coupling reaction between Br-TPA-DCM and 4-(1,2,2-triphenylvinyl)phenylboronic acid (3), with a yield of 60 %. TPE-TPA-DCM was separated and purified by column chromatography followed by recrystallization.

[0287]The specific experimental synthesis steps of the dye are as follows. 4-(1,2,2-Triphenylvinyl)phenylboronic acid (526mg, 1.4mmol) and potassium phosphate (1060mg, 5mmol) were dissolved in 50mL THF and 8mL water, and added to Br- ...

Embodiment 2

[0291] Preparation of BSA nanoparticles loaded with fluorescent compounds

[0292] BSA nanoparticles loaded with TPE-TPA-DCM were prepared by an improved desolvation method ( image 3 ). Different nanoparticles are obtained by changing the feed ratio, which refers to the mass ratio of the fluorescent compound to the BSA in the mixture, and the variation range is 0.25-5wt%. Briefly, BSA (13 mg) was first dissolved in 5 mL Milli-Q water. Subsequently, under room temperature and ultrasonic conditions, a predetermined amount of TPE-TPA-DCM in THF (8 mL, desolvating reagent) solution was added dropwise to BSA aqueous solution using a probe sensor of an ultrasonic instrument to obtain a fluorescent compound loaded The BSA nanoparticle, ultrasonic instrument is the XL2000 probe ultrasonic instrument of American MisonicIncorp company, output power is 18W. A small amount of glutaraldehyde solution (5 μL, 50%) was added to the nanoparticle solution for 4 hours at room temperature for...

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Abstract

The development of fluorescent bioprobes comprising organic fluorescent compounds that exhibit aggregation induced emission (AIE) properties, methods of producing the same, and their practical applications for in vitro and in vivo bioimaging.

Description

[0001] related application [0002] This patent application claims priority to Provisional Patent Applications Nos. 61 / 573,097 and 61 / 685,227, filed September 1, 2011, and March 14, 2012, respectively, both by the inventors of this application, and They are all incorporated herein by reference. technical field [0003] The subject of the present invention relates to the use of fluorescent organic compounds having aggregation induced emission properties. Based on biocompatible polymers, these fluorescent compounds can be formulated into uniformly sized nanoparticles with high brightness, low cytotoxicity, and selective uptake by cancer cells. Therefore, nanoparticles loaded with fluorescent compounds can be used as fluorescent bioprobes for in vitro and in vivo imaging. Background technique [0004] The emergence of non-invasive live animal fluorescence imaging technology has opened up a new development path for the diagnosis and treatment of cancer. Fluorescent imaging pr...

Claims

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Application Information

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IPC IPC(8): C09K11/06
CPCA61K49/0054A61K49/0021A61K49/0093G01N33/582C09K11/06C12Q1/37C09B23/141C09B57/00C09B57/001G01N33/574G01N2333/96466
Inventor 唐本忠秦玮刘建钊陈斯杰郭子健刘斌李凯丁丹史海斌耿军龙孙景志秦安军赵秋丽
Owner THE HONG KONG UNIV OF SCI & TECH
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