Peptide nucleic acid containing a meta-substituted phenylpyrrolocytosine exhibits a fluorescence response and increased binding affinity toward RNA

Org Lett. 2009 Nov 5;11(21):4878-81. doi: 10.1021/ol9019474.

Abstract

Peptide nucleic acids (PNA) containing meta-substituted 6-phenylpyrrolocytosine (PhpC), [mono-m-(aminoethoxy)phenyl]pyrrolocytosine (mmePhpC), [mono-m-(aminopropoxy)phenyl]pyrrolocytosine (mmpPhpC), and [mono-m-(guanidinoethoxy)phenyl]pyrrolocytosine (mmguaPhpC), have been synthesized. Meta-substituted PhpCs have been hybridized with overall higher binding affinity toward DNA and RNA than previously synthesized moePhpC or newly synthesized mopPhpC. The guanidinium-containing nucleobase, mmguaPhpC, exhibited the highest increase in binding affinity toward RNA while fluorometrically responding on the state of hybridization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cytosine / analogs & derivatives*
  • Cytosine / chemical synthesis*
  • Cytosine / chemistry
  • DNA / metabolism
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Molecular Structure
  • Oligonucleotides, Antisense / chemical synthesis*
  • Oligonucleotides, Antisense / chemistry
  • Peptide Nucleic Acids / chemical synthesis*
  • Peptide Nucleic Acids / chemistry*
  • RNA / metabolism
  • Stereoisomerism

Substances

  • Fluorescent Dyes
  • Oligonucleotides, Antisense
  • Peptide Nucleic Acids
  • RNA
  • Cytosine
  • DNA