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Issue 37, 2014
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Nitroxide-labeled pyrimidines for non-covalent spin-labeling of abasic sites in DNA and RNA duplexes

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Abstract

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 ç 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.

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

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Publication details

The article was received on 28 May 2014, accepted on 29 Jul 2014 and first published on 14 Aug 2014


Article type: Paper
DOI: 10.1039/C4OB01095G
Citation: Org. Biomol. Chem., 2014,12, 7366-7374
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    Nitroxide-labeled pyrimidines for non-covalent spin-labeling of abasic sites in DNA and RNA duplexes

    S. A. Shelke, G. B. Sandholt and S. Th. Sigurdsson, Org. Biomol. Chem., 2014, 12, 7366
    DOI: 10.1039/C4OB01095G

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