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Perylene bisimide multifunctional nano particles with adjustable size and preparation method and application thereof

A perylene imide and nanoparticle technology, which is applied in the field of preparation of multifunctional pure organic peryleneimide nanoparticles, can solve the problems of limited and restricted biological applications, and achieve uniform appearance, low price and simple synthesis Effect

Inactive Publication Date: 2017-07-04
NANJING GENERAL HOSPITAL NANJING MILLITARY COMMAND P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its application in the biological field is limited to the currently reported fluorescence imaging
As a fluorescent imaging molecule, its inherent visible light absorption and emission severely restrict the further biological application of this type of molecule

Method used

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  • Perylene bisimide multifunctional nano particles with adjustable size and preparation method and application thereof
  • Perylene bisimide multifunctional nano particles with adjustable size and preparation method and application thereof
  • Perylene bisimide multifunctional nano particles with adjustable size and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048]

[0049] Under nitrogen protection, dibromoperylene tetraanhydride (0.85g, 1.55mmol) was dispersed in 100mL of methylpyrrolidone, and then C20 primary amine (1.53g, 5.1mmol) with dovetail structure was added, acetic acid (5g, 8.33mmol ). The reaction was stirred at 85°C for 8 hours. After the reaction, it was cooled to room temperature, and poured into the reaction system into a 1N aqueous solution of hydrochloric acid, and a large amount of red precipitates could be seen to be precipitated at the same time. The red precipitate was filtered and washed with plenty of water. The crude product is obtained after drying. The obtained crude product was passed through the column with 200-300 mesh silica gel as the stationary phase and petroleum ether / dichloromethane (volume ratio 1:4) as the eluent to obtain 1.6 g of red solid with a yield of 90%. 1 H NMR (400MHz, CDCl 3 ):δ=9.50(m,2H),8.94(d,2H),8.71(s,2H),4.26–4.19(m,4H),1.79–1.70(m,4H),1.50–1.43(m,66H ),1.00(t,12H)p...

Embodiment 2

[0051]

[0052] By substituting the dibromine at the harbor position of peryleneimide with dipyrrole, the peryleneimide molecule with near-infrared absorption can be obtained. Dibromoperylene (331.8mg, 0.3mmol) and 8mL of pyrrolidine were heated to 55°C and stirred for 24 hours under the protection of the monomer. After the reaction was finished, excess pyrrolidine was removed by a rotary evaporator. The crude product was passed through a column using 200-300 mesh silica gel as a stationary phase and pure dichloromethane as an eluent to obtain 248 mg of a green solid with a yield of 75%. In this step, the isomers of peryleneimide, the isomers of 1, 6 and 1, 7 positions can be distinguished by carefully passing through the column, and the isomers with better near-infrared absorption can be obtained. Molecular structure of 1,7 positions. 1 H NMR (400MHz, CDCl 3 ):δ=8.28(d,4H),7.53(s,4H),4.25–4.19(t,4H),3.67(m,4H),2.65–2.51(m,4H),2.03–1.72(m,12H ),1.48(m,66H),1.00(t,12H)pp...

Embodiment 3

[0054]

[0055] In order to prepare an asymmetric peryleneimide molecular structure, one end of the alkyl chain at the imide site is removed. The symmetrical molecule (1.09g, 1.00mmol) obtained in the previous step and sodium hydroxide (4.68g, 83.40mmol) were added to 36mL of isopropanol solution, and heated to reflux under nitrogen protection for 0.5 hours. The reaction perylene was introduced into 50 mL of acetic acid solution. After stirring overnight, the precipitated green solid was filtered and washed with copious amounts of water and methanol. The obtained crude product was passed through a column using 200-300 mesh silica gel as a stationary phase and pure dichloromethane as an eluent to obtain an asymmetric product (0.60 g, 70%). 1 H NMR (400MHz, CDCl 3 )8.45-8.32(m,4H),7.46-7.53(d,2H),4.22(d,2H),3.85-3.65(m,4H),2.85-2.65(m,4H),2.25-1.95(m, 8H),1.48(m,33H),0.80(t,6H)ppm.HRMS:calcd.for C 52 h 63 N 3 o 5 [M+H]+809.4876; found 809.4844.

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Abstract

The invention provides a perylene bisimide compound, the structure of the compound is shown in a formula (I), wherein, R is methoxy (-OCH3), amino (-NH2), maleic anhydride (-MAL), nitrine (-N3) or hydroxy (-OH); n represents repeating unit number of polyethylene glycol, which can be an integer between 10 and 120; f and k are respectively the integers between 1 and 50, which preferably selects the integers between 2 and 20 and most preferably between 7 and 9. The invention also provides the perylene bisimide nano particles through self assembly of the perylene bisimide compound, the size of the nano particles is adjustable, the structure is uniform, through surface modification, multi-mode imaging and multifunctional targeting are realized. The invention also provides a preparation method of the perylene bisimide compound and an application of the perylene bisimide nano particles in prepataion of a diagnostic reagent for focus parts of tumour, inflammation, thrombus and lymph system and / or a treatment medicine.

Description

technical field [0001] The invention belongs to the field of biomedical engineering, and mainly relates to a preparation method of multifunctional pure organic perylene imide nanoparticles with different sizes. Based on the series of nanoparticles, biological materials such as multi-mode imaging, multifunctional targeting, and photothermal therapy are designed. . Background technique [0002] The size effect of nanoparticles plays an important role in the field of biomedicine. For example, in oncology research, the enrichment of gold nanoparticles of different sizes in tumors has been studied. After a detailed investigation of the enrichment of gold nanoparticles with different sizes from 30 to 100 nm, 60 nm was considered as the best size for enrichment. As another example, in a brain ischemia model, organic nanoparticles are used for fluorescence imaging studies of ischemic sites. Among 10, 30, and 60 nm materials, 30 nm was found to be the optimal size for enrichment i...

Claims

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Application Information

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IPC IPC(8): C07D471/04B82Y20/00B82Y30/00C09K11/06A61K41/00A61K49/22
CPCC07D471/04A61K41/0052A61K49/225B82Y20/00B82Y30/00C09K11/06C09K2211/1029
Inventor 杨震陈小元范曲立宋继彬
Owner NANJING GENERAL HOSPITAL NANJING MILLITARY COMMAND P L A
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