Synthesis and DNA binding properties of dioxime–peptide nucleic acids

• Published in: Bioorganic & medicinal chemistry letters Vol. 14; no. 11; pp. 2927 - 2930
• Main Authors: Mokhir, Andriy, Krämer, Roland, Voloshin, Yan Z., Varzatskii, Oleg A.
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 07.06.2004
• Subjects: Base Sequence; Conjugate; Copper - chemistry; DNA - metabolism; Molecular Structure; Nickel - chemistry; Nucleic Acid Denaturation; Oxime; Oximes - chemical synthesis; Oximes - pharmacology; Peptide nucleic acids; Peptide Nucleic Acids - chemical synthesis; Peptide Nucleic Acids - pharmacology; Structure-Activity Relationship; Temperature; Oxime; Peptide nucleic acids; Conjugate
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2004.03.028

Peptide nucleic acids (PNAs) C- or N-modified with dioxime ligands were prepared by solid-phase synthesis using iron(II)-clathrochelates as protected dioxime building blocks. These PNA bind complementary DNA sequence specifically, though with much reduced affinity in comparison with nonmodified PNA. The dioxime–PNA conjugates bind Cu 2+ and Ni 2+ at μM concentration. Peptide nucleic acids (PNAs) C- or N-modified with dioxime ligands were prepared by solid-phase synthesis using iron(II)-clathrochelates as protected dioxime building blocks. These PNA bind complementary DNA sequence specifically, though with much reduced affinity in comparison with nonmodified PNA. The dioxime–PNA conjugates bind Cu 2+ and Ni 2+ at μM concentration.