Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

IR820-PTX amphiphilic small-molecule prodrug in combination of photothermal therapy and chemotherapy as well as nano-particle preparation method and application thereof

A technology of IR820-PTX and IR820-COOH is applied in the field of medicine to achieve anti-tumor effect, low toxicity and solve the effect of poor water solubility

Active Publication Date: 2018-11-02
SHANDONG UNIV
View PDF5 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, the application of environment-responsive amphiphilic small-molecule prodrugs combined with near-infrared dye molecules and chemotherapeutic drugs in medicine has not been reported.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • IR820-PTX amphiphilic small-molecule prodrug in combination of photothermal therapy and chemotherapy as well as nano-particle preparation method and application thereof
  • IR820-PTX amphiphilic small-molecule prodrug in combination of photothermal therapy and chemotherapy as well as nano-particle preparation method and application thereof
  • IR820-PTX amphiphilic small-molecule prodrug in combination of photothermal therapy and chemotherapy as well as nano-particle preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1 IR820-PTX prodrug molecular synthesis

[0039] Precisely weigh a certain amount of IR820 with an analytical balance in a 100mL round-bottom flask, add anhydrous DMF to dissolve it, accurately weigh 6-aminocaproic acid in anhydrous DMF and ultrasonically mix it into the round-bottom flask, add to the mixed solution Triethylamine was reacted in an oil bath at 85°C for 4 h under the protection of nitrogen. After the reaction was complete, the anhydrous DMF in the filtrate was removed by suction filtration under reduced pressure, and the crude product was dried overnight in a vacuum oven. The dried product was redissolved in methanol, the sample was mixed with silica gel, evaporated to dryness, and the solid was separated by silica gel column, eluted with ethyl acetate and methanol gradient, and the dried IR820-COOH was collected. Precisely weigh a certain amount of IR820-COOH in a 100mL round-bottomed flask with an analytical balance, add anhydrous DMF to diss...

Embodiment 2

[0040] Embodiment 2 Proton nuclear magnetic resonance spectrum ( 1 H-NMR) identification of IR820-PTX prodrug chemical structure

[0041] Weigh about 5 mg of the IR820-PTX prodrug, dissolve it in deuterated dimethyl sulfoxide (DMSO-d6) and place it in an NMR tube, use 400MHz H NMR spectrum to measure its H NMR spectrum, using tetramethylsilane as internal standard Record the chemical shift value (ppm) of the compound. The result is as figure 1 As shown, the NMR results can confirm that the peaks of IR820 and PTX in the newly synthesized molecule can be assigned, and the chemical shift of the typical PTX reaction hydroxyl group appears, which proves the synthesis of the ester bond. pass 1 H-NMR spectrum can confirm the successful synthesis of IR820-PTX prodrug.

Embodiment 3

[0042] Example 3 High-resolution mass spectrometry (HRMS) identification of IR820-PTX prodrug chemical structure

[0043] About 1 mg of IR820-PTX prodrug was weighed, dissolved in methanol, and analyzed by high-resolution mass spectrometry. The result is as figure 2 As shown, the mass spectrometry results can be seen, the molecular ion peak [M+H] + (1780.7179) and [M-Na+2H] + The appearance of (1758.7377) proves the successful synthesis of IR820-PTX prodrug

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
Volumeaaaaaaaaaa
Login to View More

Abstract

The invention firstly discloses an amphiphilic small-molecule prodrug in combination of photothermal therapy and chemotherapy as well as a nano-particle preparation method and application thereof. Thepreparation method of the small-molecule prodrug comprises the following steps: selecting a hydrophilic near infrared dye molecule IR820 and a hydrophobic chemotherapy drug PTX, modifying, forming ester bonds between IR820-COOH and PTX so as to be bonded, thereby obtaining the small-molecule prodrug of an amphiphilic small-molecule prodrug IR820-PTX. By virtue of a simple dialysis method, the prodrug can be self-assembled in water to form nano-particles, and has good morphology and particle size distribution. Distribution in mice and antitumor tests show that the prodrug nano-particle preparation can be passively targeted to tumor tissues and greatly accumulated at tumor sites, has an excellent tumor inhibition effect, is safe, low in toxicity and small in side effects, and provides an effective scheme for combined treatment of the photothermal therapy and chemotherapy.

Description

technical field [0001] The invention relates to the field of medical technology, in particular to a preparation method, evaluation and application of amphiphilic small molecule prodrug nanoparticles combined with near-infrared dye molecule photothermal therapy and paclitaxel chemotherapy. Background technique [0002] Cancer has become a major public health problem worldwide due to its high incidence, high mortality, and low survival rate. Breast cancer is one of the malignant tumors that seriously threaten women's health. Traditional tumor treatment methods mainly include surgery, radiotherapy, chemotherapy, hormone therapy, immunotherapy, etc. With the advancement of science and technology, emerging treatment methods such as photothermal therapy, photodynamic therapy, and cryotherapy are also constantly developing. However, monotherapy often fails to achieve satisfactory results in the treatment of tumors, such as recurrence after surgery, systemic toxicity of chemotherapy...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D405/14A61K41/00A61K31/337A61K47/55A61P35/00
CPCA61K31/337A61K41/0052A61K47/55A61P35/00C07D405/14
Inventor 栾玉霞张荻李钟号
Owner SHANDONG UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com