Novel binding and efficient cellular uptake of guanidine-based peptide nucleic acids (GPNA)

Peng Zhou; Miaomiao Wang; Lei Du; Gregory W Fisher; Alan Waggoner; Danith H Ly

doi:10.1021/ja029665m

Novel binding and efficient cellular uptake of guanidine-based peptide nucleic acids (GPNA)

J Am Chem Soc. 2003 Jun 11;125(23):6878-9. doi: 10.1021/ja029665m.

Authors

Peng Zhou¹, Miaomiao Wang, Lei Du, Gregory W Fisher, Alan Waggoner, Danith H Ly

Affiliation

¹ Department of Chemistry and Center for Light Microscope Imaging and Biotechnology, Carnegie Mellon University, 4400 Fifth Avenue, Pittsburgh, Pennsylvania 15253, USA.

PMID: 12783535
DOI: 10.1021/ja029665m

Abstract

Incorporation of a guanidine functional group into the PNA backbone facilitates cellular uptake of PNA into mammalian cells with efficiency comparable to that of the TAT transduction domain. The modified PNA recognizes and binds to the complementary DNA strand in accordance with Watson-Crick recognition rules. However, unlike polypyrimidine PNA which binds to DNA in 2:1 stoichiometry, the modified PNA binds to complementary DNA in a 1:1 ratio to form a highly stable duplex.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Circular Dichroism
DNA / chemistry
DNA / metabolism*
Guanidine / chemistry
Guanidine / metabolism*
Guanidine / pharmacokinetics
Humans
Peptide Nucleic Acids / chemistry
Peptide Nucleic Acids / metabolism*
Peptide Nucleic Acids / pharmacokinetics
Spectrometry, Fluorescence
Spectrophotometry, Ultraviolet
Tumor Cells, Cultured

Substances

Peptide Nucleic Acids
DNA
Guanidine