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Amphiphilic conjugated oligomer and its preparation and drug-loaded nanoparticles prepared by its self-assembly

A nanoparticle and amphiphilic technology, applied in the field of materials, can solve problems such as long cycle time, achieve high reaction yield, strong photothermal effect, and simple synthesis method

Active Publication Date: 2022-04-19
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 3. Long cycle time

Method used

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  • Amphiphilic conjugated oligomer and its preparation and drug-loaded nanoparticles prepared by its self-assembly
  • Amphiphilic conjugated oligomer and its preparation and drug-loaded nanoparticles prepared by its self-assembly
  • Amphiphilic conjugated oligomer and its preparation and drug-loaded nanoparticles prepared by its self-assembly

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] Example 1, conjugated oligomer 3,6-bis(5-(4-(2-(diphenylamino)phenyl)thiophen-2-yl)-2,5-bis(2-(2-( 2-(2-Methoxyethoxy)ethoxy)-ethyl)-2,5-dihydropyrrole[3,4-c]pyrrole-1,4-dione (DPP-TEG-TPA) Synthesis

[0077] according to figure 1 The synthetic route shown prepares 3,6-bis(5-(4-(2-(diphenylamino)phenyl)thiophen-2-yl)-2,5-bis(2-(2-(2-( 2-Methoxyethoxy)ethoxy)-ethyl)-2,5-dihydropyrrole[3,4-c]pyrrole-1,4-dione (DPP-TEG-TPA)

[0078] 1) Synthesis of 3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

[0079] Add 90 mL of tert-amyl alcohol into a 500 mL two-necked bottle, and add sodium tert-amyl alcohol (24.8 g, 225 mmol) under an argon atmosphere. Raise the temperature to 90°C and stir until the sodium tert-amylate is completely dissolved. After adding 2-cyanothiophene (16.4 g, 150 mmol) dropwise into the system, diisopropyl succinate (12.1 g, 60 mmol) was slowly added dropwise, and it was observed that the color of the suspension changed to deep red. After ...

Embodiment 2

[0091] Example 2, Preparation of Oligomer Self-Assembled Nanoparticles DPP-TEG-TPA NPs

[0092] 1) Weigh DPP-TEG-TPA (1mg) and dissolve it in 1mLTHF, sonicate for 20min;

[0093] 2) Add the mixture to 5mL ultrapure water, and sonicate for 10min;

[0094] 3) Bubble an inert gas into the solution and stir slowly for 1 hour;

[0095] 4) After passing through a 220 μm filter membrane, dialyze overnight in a 3500 KDa dialysis bag at room temperature to remove free molecules, collect the samples in the dialysis bag, and store them at 4°C for later use.

[0096] image 3 The particle size characterization of the prepared nanoparticles DPP-TEG-TPA NPs.

[0097] Depend on image 3 It can be seen that the particle size of the nanoparticles measured by the dynamic light scattering method is about 100 nm, and the particle size is uniform.

[0098] Figure 4 The ultraviolet-visible absorption spectrum characterization of the prepared nanoparticles DPP-TEG-TPA NPs.

[0099] Depend on...

Embodiment 3

[0102] Example 3, preparation of loaded curcumin nanoparticles DPP-TEG-TPA@Cur NPs

[0103] 1) Dissolve DPP-TEG-TPA (1mg) in 1mL THF and curcumin (0.3mg) in 0.3mL THF, sonicate for 20min respectively;

[0104] 2) Heat 6mL ultrapure water bath to 30°C, mix the above two solutions, add into ultrapure water, and sonicate for 10min;

[0105] 3) Bubble an inert gas into the solution and stir slowly for 1 hour;

[0106] 4) After passing through a 220 μm filter membrane, dialyze overnight in a 3500KDa dialysis bag at room temperature to remove free molecules, collect samples in the dialysis bag, perform ultrafiltration three times to remove unloaded curcumin molecules, and store the obtained filtrate at 4°C;

[0107] Image 6 Particle size characterization of the prepared drug-loaded nanoparticles DPP-TEG-TPA@Cur NPs

[0108] Depend on Image 6 It can be seen that the particle size of the nanoparticles DPP-TEG-TPA@Cur NPs measured by the dynamic light scattering method is about 2...

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Abstract

The invention provides an amphiphilic conjugated oligomer, its preparation and drug-loaded nanoparticles prepared by its self-assembly. The general structural formula of the amphiphilic conjugated oligomer is shown in Formula I. This conjugated oligomer has amphiphilicity and self-assembly effect. After forming nanoparticles, the absorption spectrum is red-shifted and has a stronger photothermal effect; the modification of the hydrophilic side chain group can self-assemble into a photothermal effect by using hydrophobic interaction. Water-soluble nanomaterials, loaded with hydrophobic small molecule drugs and released by light and heat, have very broad application prospects in the field of biomedicine.

Description

technical field [0001] The invention belongs to the field of materials, and in particular relates to an amphiphilic conjugated oligomer and its preparation and drug-loaded nanoparticles prepared by its self-assembly. Background technique [0002] Photothermal therapy (PTT) is a non-invasive modern therapy that can be used to treat non-neoplastic diseases and cancers of various types and locations. Photothermal therapy uses heat generated by photothermal agents absorbing light of appropriate wavelengths to kill tumor cells at the site of aggregation. Due to the high photostability, complete planar and conjugated structure of the conjugated molecule, it has the characteristics of strong photostability, high extinction coefficient, and high conversion efficiency in photothermal therapy, so it has a good therapeutic effect. In addition, due to the good modifiability of conjugated molecules, there is a great possibility of synergistic application with other treatment options, an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A61K41/00A61K31/12A61K9/51A61K47/22A61P35/00
Inventor 邢成芬高梦诗高冬陈立权
Owner HEBEI UNIV OF TECH
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