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Hydrogen peroxide responsive metal-polyphenol coordination polymer nano particle as well as preparation method and application thereof

A technology of coordination polymers and nanoparticles, which can be used in medical preparations containing active ingredients, pharmaceutical formulations, wave energy or particle radiation treatment materials, etc. Hydrogen peroxide response properties, uniform size and distribution, effect of broad absorption spectrum

Active Publication Date: 2020-06-05
南京基树医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is a lack of tumor photoacoustic contrast agents with good photothermal effects in the prior art

Method used

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  • Hydrogen peroxide responsive metal-polyphenol coordination polymer nano particle as well as preparation method and application thereof
  • Hydrogen peroxide responsive metal-polyphenol coordination polymer nano particle as well as preparation method and application thereof
  • Hydrogen peroxide responsive metal-polyphenol coordination polymer nano particle as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0030] The preparation of example 1 BODIPY derivative BDP-4OH

[0031] Under the protection of nitrogen, 0.324g of fluoroborate dipyrrole (abbreviated as BODIPY, purchased from Anaiji Chemical, 1mmol) and 0.552g of 3,4-dihydroxybenzaldehyde (4mmol) were weighed and added to the two-necked flask, Add 0.5 mL of glacial acetic acid (acitic acid), 0.5 mL of piperidine (piperidine) and 10 mL of N,N-dimethylformamide (DMF) and react at 120° C. for 1 hour.

[0032] After the reaction was finished, the reaction liquid was poured into 100 mL of water, the filter residue was taken by filtration, washed several times with water, and then separated by a silica gel column to obtain 0.35 g of a black solid product with a reaction yield of 63%. The black solid product was identified by NMR, and the results are as follows: 1 H NMR (400MHz, DMSO-d6) δ9.53(s, 2H), 9.34(s, 2H), 7.59-7.56(m, 2H), 7.44-7.34(m, 4H), 7.28(d, J=16.8 Hz,2H),7.10(s,2H),6.95-6.90(m,5H),6.83(d,J=8.0Hz,2H),1.40(s,6H). ...

example 2

[0037] Example 2 Nanoparticles Preparation of BDP-Fe nanoparticles.

[0038] Weigh 11 mg of BDP-4OH (0.02 mmol) prepared in Example 1 and 5.4 mg of FeCl 3 ·6H 2 O (0.02 mmol), was dissolved in N,N-dimethylformamide, then 50 μL of triethylamine was added, and stirred at room temperature for 30 minutes. Under vigorous stirring, the reaction solution was added dropwise to 4.4 mg / mL polyethylene glycol-polypropylene glycol-polyethylene glycol block copolymer (F127, EO 106 PO 70 EO 106 ,) in an aqueous solution, and then dialyzed with a dialysis bag with a molecular weight cut-off of 10KD, and the retentate was taken to obtain a BDP-Fe nanoparticle (abbreviated as BDP-Fe NPs) solution, which was stored at room temperature for future use. The reaction principle is: the phenolic hydroxyl group in BDP-4OH coordinates with ferric ions to form nanoparticles with a three-dimensional network structure. The reaction equation is shown in Figure 9 and Figure 10 .

[0039] By ultravi...

example 3

[0041]Example 3 Study on photothermal effect of BDP-Fe nanoparticles

[0042] In two cuvettes, 1.0 mL of a 100 μg / mL BDP-Fe nanoparticle solution (prepared in Example 2) and 1.0 mL of deionized water were added, respectively. Respectively use 730nm laser (power: 1W / cm 2 ) irradiated the nanoparticle solution and deionized water for 10 minutes, and then cooled naturally for 15 minutes. During this process, a thermal imager was used to record the temperature changes of the nanoparticle solution and deionized water, and a temperature was recorded every 10 seconds. Calculate the light-to-heat conversion efficiency (η) of nanoparticle BDP-Fe according to the following formula:

[0043]

[0044] where τ s is the time constant of the sample system; m D and c D are the mass and specific heat capacity of deionized water (4.2kJ / Kg); ΔT max is the maximum temperature (23.1°C) of BDP-Fe nanoparticles after laser irradiation; I is the power of the laser (1W / cm 2 ); A is the absorb...

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Abstract

The invention provides a hydrogen peroxide responsive metal-polyphenol coordination polymer nano particle as well as a preparation method and application thereof, and belongs to the technical field offine organic synthesis. The nano particle is a nano particle of a coordination polymer formed by a polyphenol substituted BODIPY derivative and a metal. The preparation method of the nano particle comprises the following steps: adding a polyphenol substituted BODIPY derivative and a metal chloride into a solvent, reacting for 0.5-2 hours, dropwise adding into an F127 or PEG water solution, dialyzing by using a dialysis bag having molecular weight cutoff of 10KD, and saving trapped fluid, thereby obtaining the nano particle. The nano particle has an excellent hydrogen peroxide responding property, also has a wide absorption spectrum and a good photo thermal effect, can be used as a Fenton reaction nano-catalyst and a near-infrared two-region excited photo-acoustic contrast agent, and is expected to show a good application prospect in a synergistic photo thermal and chemical dynamic anti-tumor treatment.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis, and specifically relates to a hydrogen peroxide-responsive metal-polyphenol coordination polymer nanoparticle and a preparation method and application thereof. Background technique [0002] Photoacoustic imaging is an imaging method based on the phenomenon of photoacoustic conversion. During the detection process, the sample absorbs the energy of the incident laser and undergoes thermal expansion, accompanied by the generation of ultrasonic waves, and the instrument converts the received ultrasonic waves into image information. The difference in the absorption of laser energy by the sample leads to the difference in the intensity of the ultrasonic wave, thus forming the difference in light and dark of the image. Photoacoustic imaging technology combines the advantages of optical and ultrasonic imaging technologies to achieve high-resolution and high-contrast functional imaging of ...

Claims

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Application Information

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IPC IPC(8): C08G83/00A61K49/22A61K41/00A61P35/00
CPCA61K41/0052A61K49/225A61P35/00C08G83/008
Inventor 张琪董晓臣欧昌金
Owner 南京基树医药科技有限公司
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