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

Novel photosensitizer as well as preparation method and application thereof

A photosensitizer, a new type of technology, applied in the field of photosensitizers, can solve problems such as high oxygen dependence, and achieve the effect of outstanding universality and high-efficiency treatment

Pending Publication Date: 2022-04-12
SHANDONG UNIV
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the above technical problems, the present invention provides a novel photosensitizer and its preparation method and application, so as to solve the high dependence on oxygen in photodynamic therapy problems, with the aim of having good therapeutic effects in both normoxic and hypoxic states

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
  • Novel photosensitizer as well as preparation method and application thereof
  • Novel photosensitizer as well as preparation method and application thereof
  • Novel photosensitizer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045]

[0046] (1) Synthesis of compound Ⅰ

[0047]Thionyl chloride (0.3 mL, 4.0 mmol) was added to a suspension of D-biotin (300 mg, 1.23 mmol) in 10 mL of methanol, and stirred overnight at room temperature until the reaction liquid became clear and transparent. A white solid was obtained after distillation under reduced pressure. Disperse it in 10mL of methanol, slowly add hydrazine hydrate (0.48mL, 10mmol) dropwise while stirring, heat to 70°C, and react for 12h. Cool to room temperature, distill under reduced pressure, pour into a large amount of ice-cold methanol, filter with suction, and wash with methanol three times to obtain compound Ⅰ in the form of white powder.

[0048] (2) Synthesis of Compound Ⅲa

[0049] Under a nitrogen atmosphere, dissolve compound IIa (DCF-TFM, 20.4 mg, 0.025 mmol) in 5 mL of anhydrous DMF, and add 1-(3-dimethylaminopropyl)-3-ethylcarbodiethylene at 0°C Amine hydrochloride (EDCI) (24mg, 0.125mmol), 1-hydroxybenzotriazole (HOBt) (17mg,...

Embodiment 2

[0051]

[0052] (1) The synthesis of compound I is the same as in Example 1.

[0053] (2) Synthesis of compound Ⅲb

[0054] Under nitrogen atmosphere, dissolve compound Ⅱb (FL, 50mg, 0.065mmol) in 5mL of anhydrous DMF, at 0°C, add 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride Salt (EDCI) (62.8mg, 0.33mmol), 1-hydroxybenzotriazole (HOBt) (44mg, 0.33mmol) and N,N-diisopropylethylamine (DIEA) (32μL, 0.2mmol) were reacted for 2h After that, compound Ⅰ (33.5mg, 0.13mmol) was added and stirred at room temperature for 24h. Distilled under reduced pressure and purified by column chromatography (methanol / dichloromethane system=1 / 8) to obtain photosensitizer compound IIIb. The high-resolution mass spectrometry and proton NMR spectrum characterization charts of compound Ⅲb are as follows: image 3 and Figure 4 shown.

Embodiment 3

[0056]

[0057] (1) The synthesis of compound I is the same as in Example 1.

[0058] (2) Synthesis of Compound IIIc

[0059] Under a nitrogen atmosphere, dissolve compound IIc (PpIX, 30 mg, 0.053 mmol) in 3 mL of anhydrous DMF, and add 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride at 0°C salt (EDCI) (10.56mg, 0.053mmol), 1-hydroxybenzotriazole (HOBt) (7.43mg, 0.053mmol) and N,N-diisopropylethylamine (DIEA) (8.75μL, 0.053mmol) After reacting for 2h, compound I (15.3mg, 0.05mmol) was added and stirred at room temperature for 24h. Distilled under reduced pressure and purified by column chromatography (methanol / dichloromethane system=1 / 8) to obtain photosensitizer compound IIIc. The high-resolution mass spectrometry and proton NMR spectrum characterization charts of compound Ⅲc are as follows: Figure 5 and Figure 6 shown.

[0060] Figure 7 is the absorption and emission spectra of photosensitizer compound IIIa and compound IIa in ethanol, Figure 8 is t...

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

No PUM Login to View More

Abstract

The invention discloses a novel photosensitizer and a preparation method and application thereof, and the preparation method comprises the following steps: adding thionyl chloride into a methanol suspension of D-biotin, stirring overnight at room temperature until a reaction solution is clear and transparent, and carrying out reduced pressure distillation to obtain a white solid; dispersing into methanol, slowly dropwise adding hydrazine hydrate while stirring, heating, and reacting for 10-18 hours; cooling to room temperature, carrying out reduced pressure distillation, pouring methanol, carrying out suction filtration, and washing with methanol for several times to obtain a white powdery compound I; the preparation method comprises the following steps: dissolving a photosensitizer compound II with carboxyl at a terminal in anhydrous DMF in a nitrogen atmosphere, adding EDCI, HOBt and DIEA at 0 DEG C, reacting for 2 hours, adding a compound I, and stirring at room temperature for 24 hours; and performing reduced pressure distillation and purification to obtain a compound III. The novel photosensitizer prepared by the invention can solve the problem of high dependence on oxygen in photodynamic therapy, and has a good treatment effect in both normal oxygen and hypoxic states.

Description

technical field [0001] The invention relates to the technical field of photosensitizers, in particular to a novel photosensitizer and its preparation method and application. Background technique [0002] Malignant tumors have become a major threat to human life and health today. How to effectively diagnose and treat cancer is a hot topic that relevant scholars have been working on. Photodynamic therapy (Photodynamic Therapy, PDT), as a new type of non-invasive treatment method, has the advantages of tumor targeting, low dark toxicity, short treatment time and high reproducibility. [0003] Photosensitizers (Photosensitizers, PS) can convert light energy into reactive oxygen species (ROS) to induce apoptosis and tissue damage. According to different photochemical reaction processes, there are two main types of PDT: type I PDT and type II PDT. Among them, the latter is the dominant mechanism of most photosensitizers at present. However, based on the generated 1 o 2 The ty...

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): A61K47/54A61K41/00A61P35/00
Inventor 宋锋玲
Owner SHANDONG UNIV
Features
  • Generate Ideas
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com