β,γ-Bis-substituted PNA with configurational and conformational switch: preferred binding to cDNA/RNA and cell-uptake studies

Chem Commun (Camb). 2015 May 4;51(36):7693-6. doi: 10.1039/c5cc00891c.

Abstract

(S,S)- and (R,R)-β,γ-Bis-substituted PNAs were synthesized from the C-2 symmetric vicinal diamine system embedded in 1,4 dihydroxybutane and 1,4-dimethoxybutane scaffolds. (R,R)-β,γ-Bis-methoxymethyl-PNA derived from d-tartaric acid was found to be in the right configuration and conformation to be an excellent mimic of PNA, endowed with superior ability to enter into cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Binding Sites
  • Cells / metabolism*
  • DNA, Complementary / chemistry*
  • HCT116 Cells
  • Humans
  • Nucleic Acid Conformation
  • Peptide Nucleic Acids / chemical synthesis
  • Peptide Nucleic Acids / chemistry
  • Peptide Nucleic Acids / metabolism*
  • RNA / chemistry*

Substances

  • DNA, Complementary
  • Peptide Nucleic Acids
  • RNA