Inductive electron-withdrawal from ammonium ion headgroups of cationic lipids and the influence on DNA transfection

Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism Pub Date : 1998-11-02 DOI:10.1016/S0005-2760(98)00114-3

Michael H. Nantz , Ling Li , Ji Zhu , Kim L. Aho-Sharon , Debora Lim , Kent L. Erickson

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引用次数: 10

Abstract

We have prepared a panel of lipidic ammonium tetrafluoroborate salts that contain trifluoromethyl, trichloromethyl, and methyl groups attached to the headgroup. ¹⁹F-NMR analyses of the cationic lipid panel revealed that the differences in electron-withdrawal from the ammonium ion headgroup accounted for differences in ion-pairing. Exchange of the tetrafluoroborate counterion by complexation to DNA-phosphate of a reporter gene enabled us to probe the influence of inductive electron-withdrawal in cationic lipid-mediated DNA transfection. We tested the lipid panel for transfection activity in two cell lines. The results indicate that the inductive effects of electron-withdrawing functionality diminish transfection activity in modest (2–4-fold) increments. The present study suggests that the mechanism whereby poly(alcohol)- or poly(ether)-substituted headgroups improve DNA transfection is not based on electronic activation of the ammonium ion.

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阳离子脂质铵离子头基的诱导电子抽离及其对DNA转染的影响

我们制备了一组四氟硼酸脂质铵盐，它含有附着在头基上的三氟甲基、三氯甲基和甲基。阳离子脂质板的19F-NMR分析显示，铵离子头基电子撤退的差异解释了离子配对的差异。通过与报告基因的DNA-磷酸络合交换四氟硼酸盐反离子，使我们能够探索在阳离子脂质介导的DNA转染中诱导电子退出的影响。我们在两个细胞系中测试了脂质面板的转染活性。结果表明，吸电子功能的诱导效应以适度(2 - 4倍)的增量降低转染活性。目前的研究表明，聚(醇)或聚(醚)取代的头基改善DNA转染的机制不是基于铵离子的电子活化。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism

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