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Photosensitizer phospholipid compound as well as pharmaceutical composition and application of photosensitizer phospholipid compound

A technology of photosensitizer phospholipids and phospholipid compounds, which is applied in the field of medicine, can solve the problems of high price, drug leakage, and difficulty in drug efficacy, and achieve strong phototoxicity, low dark toxicity, and overcome the effect of phototoxicity reduction

Inactive Publication Date: 2016-02-03
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, the commonly used photosensitizer Visudal in clinic is the liposome form of verteporfin, and it is expensive
However, due to the fluidity of the liposome membrane, the drug is easy to leak out, making it difficult for the encapsulated drug to exert a good drug effect, and the tissue is widely distributed, resulting in certain dark toxicity

Method used

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  • Photosensitizer phospholipid compound as well as pharmaceutical composition and application of photosensitizer phospholipid compound
  • Photosensitizer phospholipid compound as well as pharmaceutical composition and application of photosensitizer phospholipid compound
  • Photosensitizer phospholipid compound as well as pharmaceutical composition and application of photosensitizer phospholipid compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0089] The synthesis of bis(methoxycarbonyl propionyl methylene carbamate-dithiodiethylene glycol-succinate) phosphatidylcholine compound (see the synthetic route figure 1 )

[0090] Dissolve 1g of methyl aminolevulinate in 20mL of chloroform, add 0.6g of triethylamine and 0.3g of triphosgene, react at room temperature for 6h, remove the solvent by rotary evaporation, dissolve the solid in 10mL of DMSO, add 0.3g of triethylamine, add 0.6 g of dithiodiethylene glycol was reacted at room temperature for 24 hours, and the resulting reaction solution was purified by column chromatography to obtain 0.31 g of methoxycarbonylpropionylmethylenecarbamate-dithiodiethylene glycol. Methoxycarbonylpropionylmethylenecarbamate-dithiodiethylene glycol, 2g of succinic anhydride dissolved in 30mL of pyridine, reacted at 40°C for 48h; the solvent was removed by rotary evaporation, the precipitate was precipitated in cold ether, washed with dilute hydrochloric acid, 0.81 g of the intermediate pr...

Embodiment 2

[0093] Synthesis of two (verteporfin-dithiodiethylene glycol-succinate) phosphatidylcholine compounds (see the synthetic route figure 2 )

[0094] Dissolve 1 g of Verteporfin in 20 mL of chloroform, add 0.5 g of CDI, activate for 1 h, add 0.6 g of dithiodiethylene glycol, 0.5 g of DBU, react at room temperature for 24 h, and the resulting reaction solution is passed through column chromatography After purification, 0.31 g of verteporfin-dithiodiethylene glycol monoester was obtained. Verteporfin-dithiodiethylene glycol monoester, 2 g of succinic anhydride dissolved in 30 mL of pyridine, reacted at 40 ° C for 48 h; the solvent was removed by rotary evaporation, the precipitate was precipitated in cold ether, washed with dilute hydrochloric acid, and the intermediate product Vertepor was obtained Fen-dithiodiethylene glycol succinate monoester 0.81g. The intermediate product verteporfin-dithiodiethylene glycol succinic acid monoester 0.8g was dissolved in 20mLDMSO, added CDI0...

Embodiment 3

[0097] The synthesis of two (HPPH-GFLG) phosphatidylcholine compounds (the synthetic route sees image 3 )

[0098] Dissolve 1 g of photochlor (HPPH) in 20 mL of DMF, add 0.5 g of CDI and 0.5 g of TEA, activate for 1 h, then add 0.5 g of N-glycyl-phenylalanyl-leucyl-glycine (GFLG) and react at room temperature After 24 hours, the reaction solution was separated by column chromatography to obtain 0.65 g of the intermediate product HPPH-GFLG. The product was dissolved in 15 mL of dimethyl sulfoxide, added with 0.6 g of CDI, 0.3 g of GPC and 0.6 g of DBU, reacted at room temperature for 24 hours, precipitated in cold ether, and separated by column chromatography to obtain bis(HPPH-GFLG) phosphatidylcholine 0.45 g. 1 HNMR (500MHz, CD 3 OD: CDCl 3 1:1): δ8.01, 7.21, 7.12, 7.08, 4.92, 4.64, 4.53, 4.32, 4.16, 4.09, 3.97, 3.77, 3.70, 3.43, 3.37, 3.30, 3.07, 3.05, 2.24, 2.22, 2.05, 1.83 , 1.75, 1.71, 1.46, 1.33, 1.31, 1.29, 1.01, 0.96. [M+H] + m / z, 2244.71.

[0099] Bis(HPPH-GF...

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Abstract

The invention discloses a photosensitizer phospholipid compound, a preparation method of the photosensitizer phospholipid compound, a pharmaceutical composition and application of the photosensitizer phospholipid compound. The pharmaceutical composition is the photosensitizer phospholipid or a combined pharmaceutical composition of the photosensitizer phospholipid and a pharmacologically acceptable carrier, and the pharmaceutical composition is in the form of a liquid preparation, a solid preparation, a semisolid preparation, a capsule, granules, a gel or an injection. The photosensitizer phospholipid compound or a liposome of the photosensitizer phospholipid is applicable to the photodynamic therapy of tumors; the photosensitizer phospholipid compound or the liposome of the photosensitizer phospholipid compound can be rapidly taken by cells and can release a photosensitizer crude drug, and under laser action, the photosensitizer phospholipid compound or the liposome of the photosensitizer phospholipid compound can rapidly release active oxygen to take a strong anti-tumor effect. The photosensitizer phospholipid compound and a liposome nanoparticle thereof can serve as a liquid preparation, a solid preparation, a semisolid preparation, a sterilized preparation and a sterile preparation; and the photosensitizer phospholipid compound and the liposome nanoparticle are low in toxicity and are applicable to the efficient treatment of various tumors.

Description

technical field [0001] The invention relates to a photosensitizer phospholipid compound used for photodynamic therapy with antitumor effect, its pharmaceutical composition and application, and relates to the technical field of medicine. Background technique [0002] Photodynamic therapy is a new tumor treatment method developed after surgery, radiotherapy, chemotherapy and immunotherapy. The principle is that by injecting photosensitizers into tumor patients, taking advantage of the uptake and retention of photosensitizers by tumor cells, the tumor site is irradiated with laser light of a specific wavelength, and a strong photochemical reaction is induced with the participation of molecular oxygen in biological tissues. , produce active oxygen components such as very active singlet oxygen and free radicals, oxidize amino acids, unsaturated fatty acids, adenosine and other biological macromolecules, and generate a large number of chemically active photooxidative secondary int...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/48A61K41/00A61K9/127A61K9/14A61P35/00
Inventor 李新松杜亚伟
Owner SOUTHEAST UNIV
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