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Nanometer photosensitizer for photodynamic antisepsis, preparation method and application thereof

A photosensitizer and nanotechnology, applied in the direction of antibacterial drugs, medical preparations with non-active ingredients, medical preparations containing active ingredients, etc., can solve the problems of low solubility, instability, easy aggregation, etc., and achieve improved hydrophobicity , Improve the effect of stability and biocompatibility

Pending Publication Date: 2018-11-27
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Photosensitizer (photosensitizer, hereinafter referred to as PS) is a key medium in the process of photodynamic antibacterial, and now more photosensitizers include thiaphenazines, porphyrins and chlorin e6, etc. Most photosensitizers (PS) The solubility in water is extremely low, and it has the disadvantages of instability and easy aggregation in aqueous solution, which seriously hinders its wide application in photodynamic antibacterial.

Method used

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  • Nanometer photosensitizer for photodynamic antisepsis, preparation method and application thereof
  • Nanometer photosensitizer for photodynamic antisepsis, preparation method and application thereof
  • Nanometer photosensitizer for photodynamic antisepsis, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] S1: Weigh N,N'-Dicyclohexylcarbodiimide (DCC) 6.9mg, N-Hydroxysuccinimide (NHS) 4.0mg and Chlorin e6 (Ce6) 10mg and dissolve in 10mL. Dimethyl sulfoxide (DMSO), stirred for 0.5 h at 25°C and protected from light to obtain an activated chlorin e6 solution;

[0042] S2: After the activated chlorin e6 solution is filtered with a filter to remove insoluble by-products, it is slowly added dropwise to a 0.5% chitosan acetic acid aqueous solution (100 mL), and protected from light at 25°C Stir the reaction for 12 hours to obtain the crude product of chlorin e6 grafted chitosan (Ce6-Chitosan);

[0043] S3: Take the crude product solution of chlorin e6 grafted chitosan (Ce6-Chitosan) and add it dropwise to the top of the dextran gel column. After it enters the gel, it is eluted with 0.5% acetic acid aqueous solution. The purified product of chlorin e6 grafted with chitosan (Ce6-Chitosan) was obtained.

[0044] S4: The purified product of chlorin e6 grafted with chitosan (Ce6-Chitosan...

Embodiment 2

[0046] S1: Weigh triethylamine (Et 3 N) 8.4mg, O-benzotriazole-tetramethylurea hexafluorophosphate (HBTU) 31.6mg and chlorin e6 (Ce6) 10mg mixed and dissolved in 10mL dimethylformamide (DMF), After stirring for 12 hours at 20°C in the dark to obtain an activated chlorin e6 solution;

[0047] S2: After the activated chlorin e6 solution is filtered with a membrane to remove insoluble by-products, it is slowly added dropwise to 3.2% N-(2-hydroxypropyltrimethyl) chitosan acetic acid aqueous solution (100mL), the reaction was stirred for 24h in the dark at 20°C to obtain the crude product of chlorin e6 grafted with N-(2-hydroxypropyltrimethyl) chitosan;

[0048] S3: Take the crude product solution of chlorin e6 grafted N-(2-hydroxypropyltrimethyl) chitosan and drop it on the top of the dextran gel column. After entering the gel, use the mass fraction as 1% acetic acid aqueous solution was eluted and purified to obtain the purified product of chlorin e6 grafted with N-(2-hydroxypropyltr...

Embodiment 3

[0051] S1: Weigh respectively 17.3mg of N,N-diisopropylethylamine (DIPEA), O-benzotriazole-N,N,N',N'-tetramethylurea tetrafluoroborate (TBTU ) 21.4 mg and 5 mg of Chlorin e6 (Ce6) were mixed and dissolved in 10 mL of dimethylformamide (DMF). After stirring for 6 hours at 30°C and protected from light, an activated Chlorin e6 solution was obtained;

[0052] S2: After the activated chlorin e6 solution is filtered with a filter membrane to remove insoluble by-products, it is slowly added dropwise to 3.2% chitosan α-aminophenoxypyrimidine phosphonate ethyl acetate aqueous solution ( 50mL), react for 48h in the dark at 30°C to obtain the crude product of chlorin e6 grafted chitosan ethyl α-aminophenoxypyrimidine phosphonate;

[0053] S3: Take the crude product solution of chlorin e6 grafted chitosan α-aminophenoxypyrimidine phosphonate and drop it onto the top of the dextran gel column. After entering the gel, use a mass fraction of 2 % Acetic acid aqueous solution was eluted and purif...

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Abstract

The invention relates to a nanometer photosensitizer for photodynamic antisepsis, a preparation method and an application thereof. According to the invention, a photosensitizer grafted chitosan or a derivative thereof is acquired through the chemical coupling reaction of a photosensitizer and chitosan or chitosan derivative; such amphiphilic polymer can be self-assembled to form the nanometer photosensitizer; the hydrophobicity of a prototype photosensitizer is improved by the nanometer photosensitizer and the stability and biocompatibility thereof can be promoted; besides, the nanometer photosensitizer with positive charges is formed in a physiological solution by the photosensitizer grafted chitosan or the derivative thereof, pathogenic microorganisms can be better taken under the effectof electrostatic interaction, oxygen molecules in surroundings are converted into singlet oxygen under the effect of visible light / near-infrared light, and the singlet oxygen can be used for photodynamic antisepsis.

Description

Technical field [0001] The invention relates to the technical fields of optical applications, nano-systems, pathogenic microorganism control, etc., in particular to a photodynamic antibacterial nano-photosensitizer, and its preparation method and application. Background technique [0002] Since the twentieth century, the emergence of multi-drug resistant bacteria due to the abuse of antibiotics has seriously threatened public health. The development of new drugs and new treatments to replace antibiotics has become a research focus in scientific research in various countries. Among them, photodynamic therapy antibacterial as a new treatment method has received widespread attention. [0003] Photodynamic antibacterial is mainly composed of photosensitizer and suitable light source. Under the irradiation of a suitable light source, the photosensitizer absorbs short-wavelength light and changes from the ground state (S 0 ) By transition to singlet state (S 1 ) And then into the excite...

Claims

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Application Information

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IPC IPC(8): C08B37/08A61K41/00A61K47/61A61K31/722A61P31/04
CPCA61K41/0071A61K47/61A61P31/04A61K31/722C08B37/003
Inventor 黄和缪文俊李媛媛张荣露
Owner NANJING UNIV OF TECH
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