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Sequence-specific and Selective Recognition of Double-stranded RNAs over Single-stranded RNAs by Chemically Modified Peptide Nucleic Acids

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Multiple Charged Purine (MCP) PNA as a Simple Mode for Cellular Uptake.

Salam Maree¹, Eylon Yavin¹

¹The Institute for Drug Research, The School of Pharmacy, The Faculty of Medicine, The Hebrew University of Jerusalem, Hadassah Ein-Kerem, Jerusalem 9112102, Israel.

ACS Polymers Au

|June 15, 2026

Summary

Modified peptide nucleic acids (PNAs) with positively charged purines show enhanced cellular uptake without toxicity. This breakthrough improves PNA delivery for biomedical applications.

Keywords:

CPP-PNA, N-methylation PNA cationic purines cellular uptake

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Area of Science:

Biochemistry
Molecular Biology
Biotechnology

Background:

Peptide nucleic acid (PNA) is a synthetic DNA analog with high stability and binding affinity.
Low membrane permeability limits PNA's biomedical use.
Modifying PNA monomers with N-methylation creates positively charged bases, enhancing DNA affinity and preventing self-duplex formation.

Purpose of the Study:

To develop inherently cell-permeable PNAs by incorporating positively charged purines.
To evaluate the cellular uptake, toxicity, and binding characteristics of these modified PNAs.
To compare the performance of modified PNAs with PNA-cell-penetrating peptide conjugates.

Main Methods:

Synthesized 16-mer PNAs with 4, 6, or 8 positively charged purines (MCP-PNAs).
Prepared control PNAs conjugated to cell-penetrating peptides (CPP-PNAs) with varying d-lysine residues.
Quantified cellular uptake using Rhodamine B labeling, flow cytometry, and confocal microscopy in OVCAR-8 cells.

Main Results:

The PNA with six positively charged purines (MCP6) demonstrated significantly higher cellular internalization than other MCP-PNAs and CPP-PNA controls.
MCP-PNAs exhibited no significant cytotoxicity.
MCP-PNAs showed comparable binding affinities and RNA mismatch discrimination to CPP-PNAs.

Conclusions:

Incorporating positively charged purines is an effective strategy to enhance PNA cellular permeability.
This approach offers a simple and efficient method for creating cell-permeable PNAs for potential biomedical applications.
MCP-PNAs represent a promising class of molecules for therapeutic and diagnostic development.