电荷反转两亲物的合成、表征及其用于 DNA 递送的体外转染活性。
Synthesis, characterization, and in vitro transfection activity of charge-reversal amphiphiles for DNA delivery.
机构信息
Departments of Biomedical Engineering and Chemistry, Boston University , Boston, Massachusetts 02215, United States.
出版信息
Bioconjug Chem. 2011 Apr 20;22(4):690-9. doi: 10.1021/bc1004526. Epub 2011 Apr 1.
Abstract
A series of charge-reversal lipids were synthesized that possess varying chain lengths and end functionalities. These lipids were designed to bind and then release DNA based on a change in electrostatic interaction with DNA. Specifically, a cleavable ester linkage is located at the ends of the hydrocarbon chains. The DNA release from the amphiphile was tuned by altering the length and position of the ester linkage in the hydrophobic chains of the lipids through the preparation of five new amphiphiles. The amphiphiles and corresponding lipoplexes were characterized by DSC, TEM, and X-ray, as well as evaluated for DNA binding and DNA transfection. For one specific charge-reversal lipid, stable lipoplexes of approximately 550 nm were formed, and with this amphiphile, effective in vitro DNA transfection activities was observed.
摘要
合成了一系列带有不同链长和端基官能团的电荷反转脂质。这些脂质的设计目的是基于与 DNA 的静电相互作用的变化来结合和释放 DNA。具体而言，可裂解的酯键位于烃链的末端。通过制备五种新的两亲分子，通过改变脂质疏水链中酯键的长度和位置来调节 DNA 从两亲分子中的释放。通过 DSC、TEM 和 X 射线对两亲分子和相应的脂质体进行了表征，并评估了它们与 DNA 的结合和 DNA 转染。对于一种特定的电荷反转脂质，形成了约 550nm 的稳定脂质体，并且使用这种两亲分子观察到有效的体外 DNA 转染活性。
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本文引用的文献
1
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Bioconjug Chem. 2010 Jun 16;21(6):1062-9. doi: 10.1021/bc100005k.
2
The effect of charge-reversal amphiphile spacer composition on DNA and siRNA delivery.电荷反转两亲体间隔物组成对 DNA 和 siRNA 递送的影响。
Bioconjug Chem. 2010 May 19;21(5):988-93. doi: 10.1021/bc9005464.
3
Chemical vectors for gene delivery: a current review on polymers, peptides and lipids containing histidine or imidazole as nucleic acids carriers.用于基因递送的化学载体：关于含组氨酸或咪唑的聚合物、肽和脂质作为核酸载体的当前综述。
Br J Pharmacol. 2009 May;157(2):166-78. doi: 10.1111/j.1476-5381.2009.00288.x.
4
Nonviral vectors for gene delivery.用于基因递送的非病毒载体。
Chem Rev. 2009 Feb;109(2):259-302. doi: 10.1021/cr800409e.
5
Progress in cationic lipid-mediated gene transfection: a series of bio-inspired lipids as an example.阳离子脂质介导的基因转染研究进展：以一系列仿生脂质为例。
Curr Gene Ther. 2008 Oct;8(5):296-312. doi: 10.2174/156652308786070989.
6
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7
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