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Synthetic method and application of water-soluble fluorescent dendrimers

A synthetic method and macromolecular technology, which is applied in the field of gene carriers of non-viral systems, can solve the problems of structural defects of dendritic macromolecules, cumbersome synthesis steps, and side reactions, and achieve reduced synthesis and purification steps and low cytotoxicity , Excellent biocompatibility effect

Active Publication Date: 2014-12-31
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the synthesis steps of these macromolecules are cumbersome, requiring the protection and deprotection of intermediate products, and the protection / deprotection process is often incomplete and accompanied by side reactions, which leads to defects in the structure of dendritic macromolecules; at the same time, these syntheses The perylene derivative dendrimers are electrically neutral, and there is no report on their application in drug carriers and gene carriers.

Method used

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  • Synthetic method and application of water-soluble fluorescent dendrimers
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1 Synthesis of Fluorescent Dendrimers Using Click Chemistry

[0043] (1) Synthesis of the first-generation fluorescent dendrimers with terminal methacrylates (A1)

[0044] Add 0.16g (0.16mmol) perylene compound A0 carrying four primary amino groups and 0.2g (3.15mmol) MAEA into a 10mL two-port reaction tube, stir overnight at room temperature under a nitrogen atmosphere, then react at 50°C for 48h, etc. After the reaction temperature dropped to room temperature, the reaction liquid was washed with n-hexane 3 times, each time with 30 mL of n-hexane, and vacuum-dried to obtain the red oily product A1 with a yield of 98%.

[0045] 1 H-NMR (400Hz, CDCl 3 ):δppm:8.20(s,4H),7.09(d,8H),6.91(d,8H),6.11(s,8H),5.56(d,8H),4.32(br,32H),4.12(t, 4H),2.87(t,16H),2.69(m,16H),2.51(t,16H),1.9(s,24H),1.59(m,4H),1.36(m,4H),0.90(t,6H ).MS(MALDI-TOF,m / z)Calc.for C 136 h 158 N 6 o 40 ,2516.73;found:2515.8.

[0046] (2) Synthesis of amino-functionalized first-generation fluore...

Embodiment 2

[0059] Except that in step (1), propyl methacryloxyacrylate is used instead of ethyl methacryloxyacrylate to react with the perylene compound A0 carrying four primary amino groups, other operations are the same as in Example 1 , to prepare the first to third generation perylene fluorescent dendrimers.

Embodiment 3

[0061] In addition to using ethyl methacryloxyethoxyethoxy acrylate in step (1) instead of ethyl methacryloxy acrylate to react with the perylene compound A0 carrying four primary amine groups, other operations Same as in Example 1, the first to third generation perylene fluorescent dendrimers were prepared.

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Abstract

The invention discloses a synthetic method and application of water-soluble fluorescent dendrimers. Fluorescent dendrimers different in generation and carrying different functional groups are prepared from the kind of water-soluble fluorescent dendrimers by the aid of a 'divergent method' or 'convergence method'. The fluorescent dendrimers peripherally carrying ammonium salt cations have excellent water solubility and biocompatibility, are capable of entering living cells, can be combined with electronegative DNA (deoxyribonucleic acid), and can serve as genetic vectors to bring exogenous nucleic acid members DNA or RNA (ribonucleic acid) into the cells. Cellular uptake experiments show that along with increase of the generation, capabilities of penetrating cell membranes and carrying genes of the dendrimers are enhanced. The synthetic method and the application have the advantages of convenience in synthesis, high efficiency, product purification and simplicity and the like, and the synthetic dendrimers are safe, low in toxicity, excellent in water solubility and good in light stability, can serve as multifunctional cell fluorescent labeled molecules and gene vectors, and are applied to scientific researches and genetic diagnosis in the field of biological medicine.

Description

technical field [0001] The invention belongs to the fields of dendritic macromolecule synthesis, gene carrier and biological cell labeling, and particularly relates to a class of synthetic and biodegradable perylene fluorescent dendritic macromolecule applied to gene carriers in non-viral systems. Background technique [0002] With the development of advanced biotechnology therapies, gene transfer systems have become more important. At present, the commonly used gene vectors mainly include viral and non-viral types. Viral gene transfection vectors have safety issues and limitations of low gene transfection efficiency, which limit their application range. The development of safe non-viral gene vectors has always been a hot research topic in the field of biomaterials. At present, the non-viral gene carrier systems that have been studied more mainly include cationic multi-polymer carriers, biodegradable polymer systems, multi-complex liposome systems, and thermosensitive polym...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12N15/87C08G83/00C09K11/06
Inventor 尹梅贞许泽军何碧程沈杰
Owner BEIJING UNIV OF CHEM TECH
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