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Amphiphilic dendrimer, synthesis method thereof, and application of amphiphilic dendrimer as drug delivery system

A technology of compound and alkyl, which is applied in the medical field and can solve the problems that the specificity and efficiency of nucleic acid or drug release need to be further improved.

Pending Publication Date: 2021-08-06
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the currently studied amphiphilic PAMAM dendrimer, after entering the cell, the assembly formed by the amphiphilic PAMAM dendrimer and the nucleic acid or the drug destroys the structure of the assembly through the "proton sponge" effect generated in the slightly acidic environment of the endosome, and then from the endosome Escape to release nucleic acid or drug, but the molecular structure remains intact, and the release specificity and efficiency of nucleic acid or drug still need to be further improved

Method used

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  • Amphiphilic dendrimer, synthesis method thereof, and application of amphiphilic dendrimer as drug delivery system
  • Amphiphilic dendrimer, synthesis method thereof, and application of amphiphilic dendrimer as drug delivery system
  • Amphiphilic dendrimer, synthesis method thereof, and application of amphiphilic dendrimer as drug delivery system

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0096] Example 1: Compound ROS-AD C 8-10 Preparation of G3

[0097]

[0098]

[0099] 1.1 ROS-AD 1-1C 8 preparation of

[0100] Add 1,8-octanediol (585.2g, 4.0mmol), triethylamine (485.6mg, 4.8mmol) and DCM (8.0mL) in sequence in the reaction flask, slowly add TsCl (762.2mg, 4.0mmol) DCM (8.0 mL) solution was stirred at room temperature until the reaction was complete. After adding water, the liquid was separated, and then the aqueous phase was extracted with DCM, the organic phase was dried and filtered, the solvent was distilled off under reduced pressure, and the residue was separated by silica gel column chromatography to obtain a colorless oily liquid ROS-AD 1-1C 8 (895.3 mg, 75%).

[0101] 1 H NMR (300MHz, CDCl 3 ): δ7.81(d, J=8.3Hz, 2H), 7.37(d, J=7.9Hz, 2H), 4.04(t, J=6.5Hz, 2H), 3.65(t, J=6.6Hz, 2H ),2.47(s,3H),1.83–1.44(m,4H),1.43–1.16(m,9H).LC-MS(ESI,m / z):301.15[M+H] + .

[0102] 1.2 ROS-AD 1-2C 8 preparation of

[0103] Add NaHCO in turn to the re...

Embodiment 2

[0123] Example 2: Compound ROS-AD C 8-18 Preparation of G3

[0124]

[0125]

[0126] 2.1 ROS-AD 1-1C 8 preparation of

[0127] Same as 1.1 of 1 in the embodiment.

[0128] 2.2 ROS-AD 1-2C 8 preparation of

[0129] Same as 1.2 in Example 1.

[0130] 2.3 ROS-AD 1-3C 18 Preparation of Compound ROS-AD 1-3C by a similar method in Example 1.3 except that decyl bromide was replaced with 1-bromooctadecane 18 (95%).

[0131] 1 H NMR (300MHz, CDCl 3 )δ=2.86(t,J=7.5Hz,2H),2.32(s,3H),1.63–1.49(m,2H),1.40–1.18(m,30H),0.87(t,J=6.6Hz,3H ).

[0132] 2.4 ROS-AD 1-4C 18 preparation of

[0133] Except with ROS-AD 1-3C 18 Replace ROS-AD 1-3C 10 In addition, compound ROS-AD 1-4C was prepared in a similar manner in Example 1.4 18 (100%).

[0134] 1 H NMR (300MHz, CDCl 3 )δ=2.52(q,J=7.1Hz,2H),1.63–1.49(m,2H),1.44–0.97(m,30H),0.88(t,J=6.6Hz,3H).

[0135] 2.5 ROS-AD 1-5C 8-18 preparation of

[0136] Except with ROS-AD 1-4C 18 Replaces ROS-AD 1-4C 10 In addition, compoun...

Embodiment 3

[0147] Example 3: Compound ROS-AD C 8-8 Preparation of G3

[0148]

[0149]

[0150] 3.1 ROS-AD 1-1C 8 preparation of

[0151] Same as 1.1 in Example 1.

[0152] 3.2 ROS-AD 1-2C 8 preparation of

[0153] Same as 1.2 in Example 1.

[0154] 3.3 ROS-AD 1-3C 8 preparation of

[0155] Except replacing decyl bromide with n-octane bromide, compound ROS-AD1-3C was prepared in a similar manner in Example 1.3 8 (95%).

[0156] 1 H NMR (300MHz, CDCl 3 )δ=2.86(t,J=7.5Hz,2H),2.32(s,3H),1.64–1.47(m,2H),1.46–0.97(m,10H),0.87(t,J=6.6Hz,3H ).

[0157] 3.4 ROS-AD 1-4C 8 preparation of

[0158] Except with ROS-AD 1-3C 8 Replace ROS-AD 1-3C 10 In addition, compound ROS-AD 1-4C was prepared in a similar manner in Example 1.4 8 (100%).

[0159] 3.5 ROS-AD 1-5C 8-8 preparation of

[0160] Except with ROS-AD 1-4C 8 Replaces ROS-AD 1-4C 10 In addition, compound ROS-AD 1-5C was prepared according to a similar method in Example 1.5 8-8 (65%).

[0161] 1 H NMR (300MHz, CDC...

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Abstract

The invention relates to a microenvironment response type amphiphilic dendrimer, a synthesis method thereof, and application of the microenvironment response type amphiphilic dendrimer as a drug delivery system. The microenvironment response type amphiphilic dendrimer is a compound with a structure as shown in a formula (I), a formula (II) or a formula (III) or pharmaceutically acceptable salt of the compound. The compound disclosed by the invention can be used as the nano delivery system based on tumor microenvironment specific response, has good solubility in an aqueous solution, can be self-assembled with a drug in the aqueous solution to form a relatively stable nano compound, can effectively deliver the loaded drug to a tumor site; and can responsively disassembl the nano-drug delivery carrier under corresponding stimulation to achieve the purpose of accurate drug release, so that the drug can be released to the focus part to the greatest extent, and the compound is a novel nano-delivery carrier.

Description

technical field [0001] The invention belongs to the field of medical technology, and in particular relates to an active oxygen responsive amphiphilic dendrimer and its pharmaceutical application as a nanometer delivery system. Background technique [0002] Malignant tumors have always been the number one killer threatening human health. The morbidity and mortality of cancer in my country ranks first in the world, and the treatment of cancer is urgent (Siegel R.L., Miller K.D., Jemal A. Cancer Satistics, 2018. CA Cancer J. Clin. 2018 , 68:7-30). Current main strategies for cancer treatment include surgical resection, chemotherapeutics (chemotherapy), radiotherapy, and gene therapy. Chemotherapy is the most widely used treatment in clinical practice. However, chemotherapeutic drugs have fast metabolism, high dosage, large toxic and side effects, poor specificity and selectivity, and some drugs have poor water solubility and are prone to drug resistance in patients (Petros R.A....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/04C07D403/14A61K9/107A61K31/704A61K47/22A61P35/00
CPCC07D249/04C07D403/14A61K9/1075A61K31/704A61K47/22A61P35/00
Inventor 刘潇璇陈朋朱丹丹韩丽丽史康洁
Owner CHINA PHARM UNIV
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