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Dithiopyridine modified zinc phthalocyanine as well as preparation method and application thereof

A technology of dithiobipyridine and dithiobipyridine, which is applied in the field of biopharmaceuticals, can solve the problems of reducing the effect of PDT on tumor treatment, limiting the wide application of PDT therapy, and insufficient tumor targeting selectivity, so as to increase the selective retention capacity, Reduced antioxidant capacity, effect of highly effective antitumor therapy

Active Publication Date: 2018-10-16
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Studies have shown that the GSH content in tumor cells is significantly higher than that in normal cells, which will cause a large amount of reactive oxygen species generated during PDT to be reduced by glutathione, seriously reducing the tumor therapeutic effect of PDT
In addition, the existing photosensitizers also have problems such as insufficient tumor targeting selectivity.
These problems limit the wide application of PDT therapy in tumor treatment

Method used

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  • Dithiopyridine modified zinc phthalocyanine as well as preparation method and application thereof
  • Dithiopyridine modified zinc phthalocyanine as well as preparation method and application thereof
  • Dithiopyridine modified zinc phthalocyanine as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] After 3-mercaptopropionic acid (0.53g) and 2,2'-dithiodipyridine (2.2g) are uniformly mixed in ethanol (5mL), glacial acetic acid (300uL) is added, and the reaction is stirred at room temperature for 8h to obtain Intermediate 1;

[0040] Intermediate 1 (121mg) was dissolved in dichloromethane (0.5mL), EDC (87.67mg) and HOBt (87.67mg) were added to catalyze 2h, ZnPc-NH 2 (50mg) dissolved in N,N-dimethylformamide (4mL) was added to the reaction system, then 39mg potassium carbonate was added, and the coupling reaction was carried out in an ice-water bath for 24h to obtain ZnPc-DTP, which was used to prepare dithiobipyridine modified phthalocyanine derivatives Flow chart as figure 2 Shown.

Embodiment 2

[0042] After 3-mercaptopropionic acid (0.53g) and 2,2'-dithiopyridine (1.65g) are uniformly mixed in ethanol (10mL), glacial acetic acid (300uL) is added, and the reaction is stirred at room temperature for 8 hours to obtain Intermediate 1;

[0043] Intermediate 1 (101.3mg) was dissolved in dichloromethane (0.5mL), EDC (73.06mg) and HOBt (63.59mg) were added to catalyze 4h, ZnPc-NH 2 (50mg) dissolved in N,N-dimethylformamide (4mL) was added to the reaction system, then 52mg of potassium carbonate was added, and the coupling reaction was carried out in an ice-water bath for 48h to obtain ZnPc-DTP.

Embodiment 3

[0045] Monitoring the reaction of ZnPc-DTP and GSH under physiological conditions

[0046] The ZnPc-DTP prepared in Example 1 was reacted with GSH under physiological conditions, and the product ZnPc-SH was verified by high-resolution mass spectrometry. The molar ratio of the reaction between ZnPc-DTP and GSH is 1:80, and triethylamine is added to make the solution weakly alkaline (pH=7.4), and react for 24 hours at room temperature. After the product is separated and purified, it is determined to be ZnPc-SH by high resolution mass spectrometry.

[0047] Such as image 3 As shown, the theoretically calculated molecular weight of ZnPc-DTP is 1411.68, and the actual measured value is 1412.28, indicating that the product is ZnPc-SH.

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Abstract

The invention discloses dithiopyridine modified zinc phthalocyanine as well as a preparation method and the application thereof. The dithiopyridine modified zinc phthalocyanine has a structural formula as shown in the specification. The novel zinc phthalocyanine disclosed by the invention is simple and convenient in preparation method, wide in raw material source and high in bioavailability; the prepared novel zinc phthalocyanine can be used as a photosensitizer in a photodynamic medicine; the zinc phthalocyanine disclosed by the invention has a natural tumor tissue targeting capability and iscapable of damaging highly expressed anti-oxidation glutathione in tumor cells after being taken by the tumor cells, furthermore light-sensitive antineoplastic activity of photodynamic therapy can beremarkably improved, and the novel zinc phthalocyanine is applicable to light-sensitive anti-tumor treatment with the photodynamic therapy.

Description

Technical field [0001] The invention belongs to biological medicine, and specifically relates to a dithiobipyridine modified zinc phthalocyanine and a preparation method and application thereof. Background technique [0002] Photodynamic therapy (PDT) is a new type of tumor treatment method. The photosensitizer is intravenously injected into the body, and the appropriate wavelength of light is selected to irradiate the photosensitizer enriched in the tumor tissue. After the light is illuminated, the photosensitizer is excited and reacts with the surrounding oxygen to generate active oxygen. The active oxygen has a strong oxidizing ability and can be oxidized. Biological macromolecules (proteins or nucleic acids, etc.), and then kill tumor tissues. Therefore, PDT treatment is based on damage caused by oxidation. PDT has the advantages of small side effects, reusability, and low drug resistance. Traditional methods for improving PDT mainly focus on improving the active oxygen ge...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61K41/00A61K47/54A61P35/00
CPCA61K41/0071A61K47/545A61P35/00C07D487/22
Inventor 魏少华周林徐锴楷姚海周家宏
Owner NANJING NORMAL UNIVERSITY
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