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Oxaliplatin conjugated prodrug, preparation method and uses thereof

A technology of oxaliplatin and prodrug, applied in the field of oxaliplatin conjugated prodrug, can solve problems such as T cell apoptosis

Active Publication Date: 2020-03-10
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Tryptophan is a nutrient for cytotoxic T lymphocytes, and kynurenine can induce T cell apoptosis, so high expression of IDO-1 can inhibit differentiation and proliferation, resulting in an immunosuppressive microenvironment

Method used

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  • Oxaliplatin conjugated prodrug, preparation method and uses thereof
  • Oxaliplatin conjugated prodrug, preparation method and uses thereof
  • Oxaliplatin conjugated prodrug, preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1. Preparation of oxidized oxaliplatin

[0054] Weigh 500mg of oxaliplatin, suspend it in 30ml of water, add 8ml of 30% hydrogen peroxide, put it in a 50ml round bottom flask, stir and react in the dark at 40°C for 10 hours, remove the solvent by rotary evaporation, and dry in vacuo to obtain oxaliplatin Platinum.

Embodiment 2

[0055] Example 2. Preparation of Monocarboxylated Oxaliplatin

[0056] Take 413 mg of oxidized oxaliplatin prepared in Example 1, dissolve it in 5 ml of anhydrous dimethyl sulfoxide, add 100 mg of succinic anhydride, react at room temperature for 12 hours, precipitate with ether, and dry in vacuo to obtain monocarboxylated oxaliplatin Platinum. The resulting material was characterized by proton nuclear magnetic resonance and mass spectrometry, and the results were as follows: figure 1 shown.

Embodiment 3

[0057] The preparation of the disulfide of embodiment 3.NLG919

[0058] Weigh 300mg of NLG919, 450mg of DMAP dissolved in 15ml of DCM in a 200ml round bottom flask. Weigh 140mg of triphosgene and dissolve it in 5ml of DCM, and slowly add it dropwise into the round bottom flask under stirring. After reacting for 30min, slowly add 500ml of bis(2-hydroxyethyl) disulfide into the reaction system dropwise. After reacting at room temperature for 20 h, the product was spin-dried and vacuum-dried to obtain the disulfide of NLG919. The resulting material was characterized by proton nuclear magnetic resonance and mass spectrometry, and the results were as follows: figure 2 shown.

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Abstract

The invention discloses an oxaliplatin conjugated prodrug, which has a structures represented by a formula 1 and a formula 2, wherein R is -NHR1 or -CH2CH2COR2, wherein R1 is selected from C2-C16 alkyl, and R2 is a group containing a small molecule inhibitor NLG919 containing a dithioethanol active group. The invention further discloses a preparation method and applications of the oxaliplatin conjugated prodrug, wherein the oxaliplatin-micromolecule conjugated drug constructed through chemical bonds is expected to improve the treatment of oxaliplatin and achieve drug combination.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and in particular relates to an oxaliplatin-coupled prodrug, its preparation method and application. Background technique [0002] Chemotherapy is one of the main means of current cancer treatment, among which (bivalent) platinum drugs have the characteristics of good anti-cancer effect and wide indications. At present, cisplatin and oxaliplatin are mainly used in clinical treatment for many patients. a malignant tumor. However, oxaliplatin is prone to cause severe gastrointestinal reactions, nephrotoxicity and bone marrow toxicity. At the same time, oxaliplatin can easily lead to acquired drug resistance, which seriously reduces the curative effect and limits the clinical application effect of oxaliplatin. Using a covalent coupling strategy to construct a conjugated prodrug of oxaliplatin and active molecules is expected to reduce the dosage of oxaliplatin and reduce the...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61K31/555A61P35/00
CPCA61P35/00C07F15/0093A61K31/395A61K31/555A61K31/704C07D487/04C07F15/00
Inventor 于海军李亚平牛自飞冯兵侯博
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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