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Preparation and application of 5-aminolevulinic acid-camptothecin micromolecular prodrug

A technology of aminolevulinic acid and camptothecin, which is applied in the directions of non-active ingredients medical preparations, active ingredients-containing medical preparations, pharmaceutical formulas, etc., can solve the problem of poor selectivity, low efficacy of single chemotherapy, and low drug load. And other issues

Inactive Publication Date: 2020-10-30
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In view of the disadvantages of the existing monomolecular polymeric prodrugs, such as poor selectivity, low drug loading capacity, and difficulty in ensuring the selective and controllable release of drugs, and the curative effect of single chemotherapy is low

Method used

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  • Preparation and application of 5-aminolevulinic acid-camptothecin micromolecular prodrug
  • Preparation and application of 5-aminolevulinic acid-camptothecin micromolecular prodrug
  • Preparation and application of 5-aminolevulinic acid-camptothecin micromolecular prodrug

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Embodiment 1

[0027] Example 1 Preparation of a 5-aminolevulinic acid-camptothecin small molecule prodrug

[0028] A kind of total synthetic schematic diagram of 5-aminolevulinic acid-camptothecin small molecule prodrug as figure 1 As shown, it mainly includes the following steps:

[0029] (1) Preparation of camptothecin CPT precursor BHD-CPT with disulfide bonds, the synthesis route is shown below, including the following steps: under the conditions of 25°C and 2-10Pa argon atmosphere, camptothecin CPT ( 376.2mg, 1.08mmol) and 4-lutidine DMAP (420.6mg, 3.42mmol) were dissolved in anhydrous dichloromethane DCM (15mL); triphosgene BTC (123mg, 0.396mmol) was dissolved in anhydrous DCM ( 15mL), then the BTC solution dissolved in anhydrous DCM was added dropwise to the reaction system, and the reaction was protected from light for 0.5-1h; 2-hydroxyethyl disulfide BHD (830mg, 5.4mmol) was dissolved in anhydrous tetrahydrofuran THF (4mL), then slowly drop the BHD solution dissolved in anhydrous...

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Abstract

The invention discloses preparation and application of a 5-aminolevulinic acid-camptothecin micromolecular prodrug. A preparation method comprises the following steps: (1) preparing a disulfide bond-containing camptothecin monomer BHD-CPT; (2) preparing CPT-SS-NPC; and (3) reacting a photosensitizer ALA with CPT-SS-NPC to prepare CPT-SS-ALA. Benefited from the amphiphilic structure of the drug conjugate, the drug conjugate can be self-assembled in water to form nanoparticles, and has the advantages of high micelle stability, controllable micelle shape, high drug loading capacity, low toxic andside effects, good drug controlled release and the like. In a reductive tumor microenvironment, disulfide bonds in the drug nanoparticles are broken, a chemotherapeutic drug CPT is released, meanwhile, the photosensitizer ALA continues to generate singlet oxygen under laser irradiation to kill cancer cells, and multi-modal synergistic treatment of tumors is achieved.

Description

technical field [0001] The invention relates to the field of macromolecular chemical drugs, in particular to a preparation method and application of a 5-aminolevulinic acid-camptothecin small-molecule prodrug nano-micelle. Background technique [0002] Camptothecin (CPT, chemical structure: C 20 h 16 N 2 o 4 , CAS No.: 7689-03-4, relative molecular weight: 348.43) is a plant anticancer drug extracted from camphor trees distributed in south-central and southwest China. It has a good curative effect on gastrointestinal tract and head and neck cancer. Camptothecin is a cytotoxic quinoline alkaloid that inhibits DNA topoisomerase (TOPOI). [0003] 5-Aminolevulinic acid (ALA, CAS number: 5451-09-6), is a second-generation photosensitizer and a photodynamic therapy (PDT) drug. ALA is an endogenous biochemical substance, through ALA dehydratase and a series of enzymatic actions to generate protoporphyrin IX (PPIX) with strong photosensitivity. The cancer tissue containing PP...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/69A61K47/55A61K31/4745A61K41/00A61P35/00
CPCA61K31/4745A61K41/0061A61K47/55A61K47/6907A61P35/00A61K2300/00
Inventor 许志刚高原卢奕贾蝶马宪彬康跃军
Owner SOUTHWEST UNIV
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