Fat-soluble photosensitizer, and preparation method and application thereof

A photosensitizer, fat-soluble technology, used in the medical and biomedical fields, can solve the problems of photosensitizer enrichment concentration and retention time limitation, poor fat solubility, and difficulty in achieving therapeutic effects, achieving significant therapeutic effects and no resistance. Medicinal properties and the effect of reducing side effects of drugs

Active Publication Date: 2018-04-13
THE THIRD XIANGYA HOSPITAL OF CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Secondly, the aggregation concentration of existing photosensitizers in skin tumor tissues needs to be improved. For example, China invented "Photosensitizer Sodium Chlorophyllin Derivatives and Its Preparation Method and Application", application number: 201210169784.1; the sodium chlorophyllin used Salt derivatives are combined with traditional photosensitizers. Although water-soluble sodium chlorophyllin enhances the penetration ability of photosensitizers, due to its poor fat solubility, the enrichment concentration and retention time of photosensitizers in tumor tissues are greatly limited. limitations, it is still difficult to achieve a good therapeutic effect

Method used

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  • Fat-soluble photosensitizer, and preparation method and application thereof
  • Fat-soluble photosensitizer, and preparation method and application thereof
  • Fat-soluble photosensitizer, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1: the synthetic route of fat-soluble photosensitizer is as follows:

[0046] (1) Combine 1-naphthylamine with chlorine-containing compounds Reaction in the ethanol solvent of 55 ℃-60 ℃, obtains intermediate product A, and its reaction formula is:

[0047]

[0048] Tetracarboxy compound Reaction with KOH or NaOH solution to obtain intermediate product B;

[0049] (2) react intermediate product A and intermediate product B in ethanol solvent by the molar ratio of 2-2.5:3-4, obtain intermediate product C, reaction formula is:

[0050]

[0051] (3) Vitamin E and intermediate product C are reacted in acetone solvent to obtain fat-soluble photosensitizer ( figure 1 ), the reaction formula is:

[0052]

[0053] The following is the hydrogen spectrum of the final product ( figure 2 ) and carbon spectrum ( image 3 ), which proves that the present invention has successfully obtained the above-mentioned target product.

Embodiment 2

[0054] Example 2: Test of inhibition of skin tumor cell activity by long-acting fat-soluble photodynamic external preparations containing vitamin E fragments

[0055] MTT method is a method to detect cell survival and growth. The detection principle is that succinate dehydrogenase in the mitochondria of living cells can reduce exogenous MTT to water-insoluble blue-purple crystalline formazan (Formazan) and deposit in the cells, while dead cells do not have this function. Dimethyl sulfoxide (DMSO) can dissolve formazan in cells, and its light absorption value is measured at a wavelength of 490nm by an enzyme-linked immunosorbent detector, which can indirectly reflect the number of living cells.

[0056] (1) Experimental method

[0057] The squamous cell carcinoma A-431 cell line was cultured in DMEM medium with 10% calf serum, added with 100IU / L penicillin and 100mg / L streptomycin, and placed in a constant temperature incubator at 37°C and 5% CO2. Cultivate, after the cells g...

Embodiment 3

[0061] Example 3: Long-acting fat-soluble photodynamic preparation containing vitamin E fragments induces apoptosis in skin tumors

[0062] Annexin V is a reagent for detecting cell apoptosis. In normal cells, phosphatidylserine is only distributed on the inner side of the lipid bilayer of the cell membrane. In the early stage of cell apoptosis, the membrane phosphatidylserine (PS) is turned from the inner side of the lipid membrane to outside. Therefore, Annexin V is a sensitive indicator for detecting early cell apoptosis. PI (propidium iodide) is a nuclear staining reagent that can stain DNA. Although PI cannot pass through the living cell membrane, it can pass through the damaged cell membrane and stain the nucleus. Therefore, the combination of Annexin V and PI can stain live and dead cells at the same time.

[0063] (1) Experimental method

[0064] The squamous cell carcinoma A-431 cell line was cultured in DMEM medium with 10% calf serum, added with 100IU / L penicilli...

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Abstract

The invention discloses a fat-soluble photosensitizer, and a preparation method and application thereof. According to the invention, vitamin E derivatives and inorganic salts of the derivatives are combined with a photosensitizer for treating skin tumors, and skin collagen fibers can be repaired with the help of the protective effect of the vitamin E on healthy skins while tumor cells can be effectively killed, so that the side effects of medicines are greatly reduced. According to the fat-soluble photosensitizer disclosed by the invention, the drug metabolism rate is slowed, so that the drugeffect is more durable. The photosensitizer containing the vitamin E derivatives can generate more free radicals, so that the tumor cells can be killed more efficiently and quickly. The required dosage is far lower than a required dosage of 5-ALA used in the market, antibiotics are not contained, drug resistance is not generated, and the photosensitizer is safe, non-toxic, economical and practical.

Description

technical field [0001] The invention relates to a fat-soluble photosensitizer and its preparation method and application, belonging to the fields of medical treatment and biomedicine. . Background technique [0002] Cutaneous squamous cell carcinoma is a type of skin tumor. Its main features are: initially it is a blemish-like raised mass, the base is hard, the surface is rough like cauliflower, telangiectasia can be seen, and spike-like cutin is common on the top. Skin squamous cell carcinoma co-infected with viscous pus, foul smell and pain. Its malignancy is high, and it is easy to transfer, and regional lymph node metastasis is more common, which seriously affects the physical and mental health of patients. [0003] The anti-cancer principle of Photodynamic Therapy (PDT) is a treatment method that mainly affects the target tissue and has dual selectivity. Its dual selectivity is based on the difference in the concentration of the photosensitizer in normal and target ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D421/12A61K41/00A61P35/00A61P17/00
CPCA61K41/0057C07D421/12
Inventor 王臻康健黄进华陈静柳岸宋相志郭克华马思祺吴梦媛向亚平丁澍郭爱元陈则夷朱宏王海蓉杨茜妍王萍
Owner THE THIRD XIANGYA HOSPITAL OF CENT SOUTH UNIV
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