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A self-luminescent polymer material responsive to active oxygen and myeloperoxidase in situ, its preparation method and its application

A technology of myeloperoxidase and polymer materials, which is applied in the field of biomedicine, can solve the problems of poor tissue penetration of light waves, short wavelengths, and limitations in in vivo imaging applications, and achieve diversification of drug delivery routes, improvement of solubility, and preparation The process is stable and controllable

Active Publication Date: 2020-12-04
ARMY MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its maximum emission wavelength is 425nm, the wavelength is short, and the light wave tissue penetration is poor, which limits the application of in vivo imaging.

Method used

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  • A self-luminescent polymer material responsive to active oxygen and myeloperoxidase in situ, its preparation method and its application
  • A self-luminescent polymer material responsive to active oxygen and myeloperoxidase in situ, its preparation method and its application
  • A self-luminescent polymer material responsive to active oxygen and myeloperoxidase in situ, its preparation method and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042]Under nitrogen protection, 0.1mM chlorin e6 and 1mM 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / N-hydroxysuccinimide were dissolved in 5ml anhydrous dihydrogen In methyl sulfoxide, react at 0°C for 12 hours to obtain the chlorin e6 intermediate with activated carboxyl group; add 0.2mM luminol (corresponding to the content of the invention, the first substituent in ①), and react at 0°C for 24 hours to obtain Luminol-substituted chlorin e6 compound; then, add 0.2mM molecular weight of 400Da amino-terminated polyethylene glycol, react at 0°C for 24 hours to obtain chlorin e6 bonded luminol as hydrophobic unit, polyethylene glycol as the amphiphilic polymer of the hydrophilic segment; finally, the amphiphilic polymer is transferred to a dialysis bag with a molecular weight cut-off of 1000Da, dialyzed in ultrapure water for 48 hours, and freeze-dried at -60°C to obtain Reactive oxygen and myeloperoxidase responsive self-luminescent polymer materials.

Embodiment 2

[0044] Under nitrogen protection, 0.1mM chlorin e6 and 1.5mM 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / N-hydroxysuccinimide in 10ml without In water N,N-dimethylformamide, react at 25°C for 18 hours to obtain the carboxyl-activated chlorin e6 intermediate; add 1mM isoluminol (corresponding to the content of the invention, the second substituent in ①), 25 ℃ reaction for 72 hours to obtain isoluminol-substituted chlorin e6 compound; add 0.5mM amino-terminated polyethylene glycol with a molecular weight of 1000Da, and react at 25 ℃ for 72 hours to obtain chlorin e6-isoluminol The amphiphilic polymer is a hydrophobic unit and polyethylene glycol is a hydrophilic segment; the amphiphilic polymer is transferred to a dialysis bag with a molecular cutoff of 2000, dialyzed in ultrapure water for 72 hours, and freeze-dried at -57°C. Reactive oxygen and myeloperoxidase-responsive self-luminescent polymer materials were obtained.

Embodiment 3

[0046] Under nitrogen protection, 0.1mM chlorin e6 and 2mM 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / N-hydroxysuccinimide in 20ml of anhydrous In N,N-dimethylacetamide, react at 50°C for 24 hours to obtain the carboxyl-activated chlorin e6 intermediate; add 2mM 8-amino-5-chloro-7-phenylpyrido[3,4-di] Pyridazine-1,4(2H,3H)dione (L-012) (corresponding to the content of the invention, the third substituent in ①), react at 50°C for 100 hours to obtain 8-amino-5-chloro-7-phenyl Pyrido[3,4-di]pyridazine-1,4(2H,3H)dione substituted chlorin e6 compound; add 2mM amino-terminated polyethylene glycol with a molecular weight of 2000, and react at 50°C for 100 hours An amphiphilic polymer with chlorin e6 / L-012 as the hydrophobic unit and polyethylene glycol as the hydrophilic segment was obtained; the amphiphilic polymer was transferred to a dialysis bag with a molecular cutoff of 5000 Da, and ultrapure water Dialyzed in medium for 72 hours, and freeze-dried at -55°C to ...

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Abstract

The invention discloses an in-situ reactive oxygen species and myeloperoxidase responsive self-luminous polymer material as well as a preparation method and application thereof and belongs to the field of biomedicines. The in-situ reactive oxygen species and myeloperoxidase responsive self-luminous polymer material has a chemical structure shown as follows. The in-situ reactive oxygen species andmyeloperoxidase responsive self-luminous polymer material takes photo-sensitizer porphyrin e6 as a basic skeleton and is chemically bonded with chemiluminescent small molecule luminol or a derivativethereof and polyethylene glycol. Nano-particles are formed by self-assembly in an aqueous solution, the specificity responds to a highly-reactive oxygen species and myeloperoxidase horizontal micro-environment, and based on a chemiluminescence resonance energy transfer effect, near-infrared light is emitted for self-luminous imaging; an in-situ photodynamic therapy function is played along with the generation of singlet oxygen. The polymer material disclosed by the invention has the beneficial effects that the preparation process is simple, reaction conditions are easy to control, and the application prospect is wide.

Description

technical field [0001] The invention belongs to the field of biomedicine, and in particular relates to a preparation method and application of an in-situ active oxygen and myeloperoxidase responsive self-luminous polymer material. Background technique [0002] Reactive oxygen species (ROS), also known as reactive oxygen species, are the metabolites of the body's physiological activities, but excessive ROS are harmful to many diseases, such as inflammatory diseases, cardiovascular diseases, aging, diabetes, tumors and neurodegenerative disorders have a major impact on the development of 1-5 . In view of the potential threat of ROS to the health of the body, timely detection and effective removal of ROS are of great significance for the monitoring and treatment of diseases related to ROS levels 6-10 . In recent years, the development of materials for ROS-responsive drug delivery systems has emerged in an endless stream, and this method of using disease-specific microenviron...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/333C07D487/22A61K41/00A61K47/22A61K49/00A61P1/16A61P9/10A61P29/00A61P35/00
CPCA61K41/0071A61K47/22A61K49/0002A61K49/0036A61P1/16A61P9/10A61P29/00A61P35/00C07D487/22C08G65/33396
Inventor 张建祥徐晓秋安会杰张定林窦寅
Owner ARMY MEDICAL UNIV
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