ArticleBiochemistry2021
The 2-Aminopyridine Nucleobase Improves Triple-Helical Recognition of RNA and DNA When Used Instead of Pseudoisocytosine in Peptide Nucleic Acids.
Article in Biochemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 29 citations in OpenAlex.
- Synthesis and RNA-Binding Properties of Heteroaryl Amino Pyridine Nucleobases for Triple-Helix-Forming Peptide Nucleic Acids.The Journal of organic chemistry · 2026Article
- 5-Triazolyl uracil improves nucleobase stacking, pyrimidine recognition, biological activity, and specificity of RNA-binding triplex-forming peptide nucleic acids.Nucleic acids research · 2026Article
- Nucleobase-Modified Triplex-Forming Peptide Nucleic Acids for Sequence-Specific Recognition of Double-Stranded RNA and DNA.Methods in molecular biology (Clifton, N.J.) · 2026Article
- Synthesis and Incorporation of a pH-Responsive Nucleoside Into DNA Sequences.Chembiochem : a European journal of chemical biology · 2025Article
- Recognition of Noncanonical RNA Base Pairs Using Triplex-Forming Peptide Nucleic Acids.ACS chemical biology · 2025Article
- Isoorotamide-based peptide nucleic acid nucleobases with extended linkers aimed at distal base recognition of adenosine in double helical RNA.Beilstein journal of organic chemistry · 2025Article
- Enhancing RNA inhibitory activity using clamp-G-modified nucleobases.Cell reports. Physical science · 2024Article
- Article
- Triplex-forming peptide nucleic acids as emerging ligands to modulate structure and function of complex RNAs.Chemical communications (Cambridge, England) · 2024Review
- Comparison of 2-Aminopyridine and 4-Thiopseudisocytosine PNA Nucleobases for Hoogsteen Recognition of Guanosine in RNA.ACS omega · 2024Article
- Recent Advancements in Development and Therapeutic Applications of Genome-Targeting Triplex-Forming Oligonucleotides and Peptide Nucleic Acids.Pharmaceutics · 2023Review
- TFOFinder: Python program for identifying purine-only double-stranded stretches in the predicted secondary structure(s) of RNA targets.PLoS computational biology · 2023Article
- Triplex-Forming Peptide Nucleic Acid Controls Dynamic Conformations of RNA Bulges.Journal of the American Chemical Society · 2023Article
- Cellular uptake of 2-aminopyridine-modified peptide nucleic acids conjugated with cell-penetrating peptides.Biopolymers · 2022Article
- Fluorobenzene Nucleobase Analogues for Triplex-Forming Peptide Nucleic Acids.Chembiochem : a European journal of chemical biology · 2022Article
- Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications.Beilstein journal of organic chemistry · 2021Review
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Pseudoisocytosine (J), a neutral analogue of protonated cytosine, is currently the gold standard modified nucleobase in peptide nucleic acids (PNAs) for the formation of J·G-C triplets that are stable at physiological pH. This study shows that triple-helical recognition of RNA and DNA is significantly improved by using 2-aminopyridine (M) instead of J. The positively charged M forms 3-fold stronger M+·G-C triplets than J with uncompromised sequence selectivity. Replacement of six Js with Ms in a PNA 9-mer increased its binding affinity by ∼2 orders of magnitude. M-modified PNAs prefer binding double-stranded RNA over DNA and disfavor off-target binding to single-stranded nucleic acids. Taken together, the results show that M is a promising modified nucleobase that significantly improves triplex-forming PNAs and may provide breakthrough developments for therapeutic and biotechnology applications.
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Registered trials
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