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 journalArticle

12 Scopus citations


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 languageEnglish (US)
Pages (from-to)219-223
Number of pages5
JournalBiochimica et Biophysica Acta - Lipids and Lipid Metabolism
Issue number2-3
StatePublished - Nov 2 1998



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

ASJC Scopus subject areas

  • Biochemistry
  • Endocrinology
  • Biophysics

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