Influence of salt and pH on the hydrophobicity parameters of antisense nucleosides studied by reversed-phase thin-layer chromatography and multivariate mathematical-statistical methods

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Abstract

The lipophilicity and specific hydrophobic surface area of 12 8-substituted 2'-deoxyadenosine and 17 5-substituted-2'-deoxyuridine derivatives were determined by reversed-phase thin-layer chromatography in ion-free eluents and in eluents containing sodium chloride, sodium acetate and acetic acid. The strength and selectivity of the effect of eluent additives were separated by use of spectral mapping technique followed by two-dimensional nonlinear mapping. The relationship between the structural characteristics and hydrophobicity parameters was elucidated by stepwise regression analysis. Eluent additives exert a considerable influence on both hydrophobicity parameters. The effect of sodium chloride and acetic acid was higher than that of sodium acetate. The strength and selectivity of the sensitivity of nucleosides towards eluent additives significantly depended on the character of the ring structure and on the length of the apolar alkyl chain. The influence of the degree of unsaturation and the branching of the alkyl substituent was negligible. Copyright (C) 1999 Elsevier Science B.V.

Original languageEnglish
Pages (from-to)21-30
Number of pages10
JournalJournal of biochemical and biophysical methods
Volume41
Issue number1
DOIs
Publication statusPublished - Aug 30 1999

Keywords

  • Antisense nucleosides
  • Lipophilicity
  • Spectral mapping

ASJC Scopus subject areas

  • Biophysics
  • Biochemistry

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