Cross-linker for Formyl Groups of Abasic Sites in Double-stranded Oligonucleotides

　N,N'-(Naphthalene-1,5-diyl)bis[2-(aminooxy)acetamide] (aoNao, 1) can recognize a pair of abasic sites in double-stranded oligonucleotides and covalently cross-link their formyl groups.¹⁾ The cross-linked duplex is thermally stable, has a rigid conformation and shows high nuclease resistance.²⁾ Due to these properties, the cross-linked duplex is applicable for modification of antisense oligonucleotides.^3,4) Needless to say, 1 can be used as a typical diamine cross-linker.

References

• 1) Interstrand cross-link of DNA by covalently linking a pair of abasic sites
  • K. Ichikawa, N. Kojima, Y. Hirano, T. Takebayashi, K. Kowata, Y. Komatsu, Chem. Commun. 2012, 48, 2143.
• 2) Electrochemical properties of interstrand cross-linked DNA duplexes labeled with Nile blue
  • Y. Mie, K. Kowata, N. Kojima, Y. Komatsu, Langmuir 2012, 28, 17211.
• 3) Function Control of Anti-microRNA Oligonucleotides Using Interstrand Cross-Linked Duplexes
  • Y. Mie, Y. Hirano, K. Kowata, A. Nakamura, M. Yasunaga, Y. Nakajima, Y. Komatsu, Mol. Ther. Nucleic. Acids 2018, 10, 64.
• 4) Inhibition of breast cancer cell proliferation with anti-microRNA oligonucleotides flanked by interstrand cross-linked duplexes
  • S. Okumura, Y. Hirano, Y. Komatsu, Nucleosides Nucleotides Nucleic Acids 2020, 39, 225.

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