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The 2-Aminopyridine Nucleobase Improves Triple-Helical Recognition of RNA and DNA When Used Instead of Pseudoisocytosine in Peptide Nucleic Acids.
Ryan, Christopher A; Brodyagin, Nikita; Lok, Justin; Rozners, Eriks.
Afiliação
  • Ryan CA; Department of Chemistry, Binghamton University, The State University of New York, Binghamton, New York 13902, United States.
  • Brodyagin N; Department of Chemistry, Binghamton University, The State University of New York, Binghamton, New York 13902, United States.
  • Lok J; Department of Chemistry, Binghamton University, The State University of New York, Binghamton, New York 13902, United States.
  • Rozners E; Department of Chemistry, Binghamton University, The State University of New York, Binghamton, New York 13902, United States.
Biochemistry ; 60(24): 1919-1925, 2021 06 22.
Article em En | MEDLINE | ID: mdl-34097400
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.
Assuntos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Ácidos Nucleicos Peptídicos / Aminopiridinas / Conformação de Ácido Nucleico Idioma: En Revista: Biochemistry Ano de publicação: 2021 Tipo de documento: Article País de afiliação: Estados Unidos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Ácidos Nucleicos Peptídicos / Aminopiridinas / Conformação de Ácido Nucleico Idioma: En Revista: Biochemistry Ano de publicação: 2021 Tipo de documento: Article País de afiliação: Estados Unidos