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

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

doi:10.1016/S0005-2760(98)00114-3

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

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

Research output: Contribution to journal › Article

12 Scopus citations

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. Copyright (C) 1998.

Original language	English (US)
Pages (from-to)	219-223
Number of pages	5
Journal	Biochimica et Biophysica Acta - Lipids and Lipid Metabolism
Volume	1394
Issue number	2-3
DOIs	https://doi.org/10.1016/S0005-2760(98)00114-3
State	Published - Nov 2 1998

Keywords

Amine quaternization
Cationic lipid
Counterion
DNA
Gene transfer
Lipoplex
Nuclear magnetic resonance
Transfection

ASJC Scopus subject areas

Biochemistry
Endocrinology
Biophysics

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Nantz, M. H., Li, L., Zhu, J., Aho-Sharon, K. L., Lim, D., & Erickson, K. L. (1998). Inductive electron-withdrawal from ammonium ion headgroups of cationic lipids and the influence on DNA transfection. Biochimica et Biophysica Acta - Lipids and Lipid Metabolism, 1394(2-3), 219-223. https://doi.org/10.1016/S0005-2760(98)00114-3

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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. Copyright (C) 1998.",

keywords = "Amine quaternization, Cationic lipid, Counterion, DNA, Gene transfer, Lipoplex, Nuclear magnetic resonance, Transfection",

author = "Nantz, {Michael H.} and Ling Li and Ji Zhu and Aho-Sharon, {Kim L.} and Debora Lim and Erickson, {Kent L}",

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AU - Nantz, Michael H.

AU - Li, Ling

AU - Zhu, Ji

AU - Aho-Sharon, Kim L.

AU - Lim, Debora

AU - Erickson, Kent L

PY - 1998/11/2

Y1 - 1998/11/2

N2 - 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. Copyright (C) 1998.

AB - 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. Copyright (C) 1998.

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KW - Cationic lipid

KW - Counterion

KW - DNA

KW - Gene transfer

KW - Lipoplex

KW - Nuclear magnetic resonance

KW - Transfection

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