Nitroxide-labeled pyrimidines for non-covalent spin-labeling of abasic sites in DNA and RNA duplexes

Sandip Shelke, Gunnar Birgir Sandholt, Snorri Sigurdsson

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)


Non-covalent and site-directed spin labeling gives easy access to spin-labeled nucleic acids for the study of their structure and dynamics by electron paramagnetic resonance (EPR) spectroscopy. In a search for improved spin labels for non-covalent binding to abasic sites in duplex DNA and RNA, ten pyrimidine-derived spin labels were prepared in good yields and their binding was evaluated by continuous wave (CW)-EPR spectroscopy. Most of the spin labels showed lower binding affinity than the previously reported label c towards abasic sites in DNA and RNA. The most promising labels were triazole-linked spin labels and a pyrrolocytosine label. In particular, the N1-ethylamino derivative of a triazole-linked uracil spin label binds fully to both DNA and RNA containing an abasic site. This is the first example of a spin label that binds fully through non-covalent interactions with an abasic site in RNA.
Original languageEnglish
Pages (from-to)7366-7374
JournalOrganic and Biomolecular Chemistry
Issue number37
Publication statusPublished - 2014

Other keywords

  • Cleave apurinic sites
  • Distance measurement
  • Nucleic acid
  • EPR Spectroscopy
  • Click chemistry
  • Fluorescence
  • Nucleoside
  • Ligand
  • Kjarnsýrur
  • Litrófsgreining
  • Sameindaerfðafræði


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