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Issue 28, 2014
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Synthesis and photophysical characterisation of new fluorescent triazole adenine analogues

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Abstract

Fluorescent nucleic acid base analogues are powerful probes of DNA structure. Here we describe the synthesis and photo-physical characterisation of a series of 2-(4-amino-5-(1H-1,2,3-triazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl) and 2-(4-amino-3-(1H-1,2,3-triazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl) analogues via Sonogashira cross-coupling and [3 + 2]-cycloaddition reactions as the key steps in the synthesis. Compounds with a nitrogen atom in position 8 showed an approximately ten-fold increase in quantum yield and decreased Stokes shift compared to analogues with a carbon atom in position 8. Furthermore, the analogues containing nitrogen in the 8-position showed a more red-shifted and structured absorption as opposed to those which have a carbon incorporated in the same position. Compared to the previously characterised C8-triazole modified adenine, the emissive potential was significantly lower (tenfold or more) for this new family of triazoles-adenine compounds. However, three of the compounds have photophysical properties which will make them interesting to monitor inside DNA.

Graphical abstract: Synthesis and photophysical characterisation of new fluorescent triazole adenine analogues

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Publication details

The article was received on 02 May 2014, accepted on 03 Jun 2014 and first published on 03 Jun 2014


Article type: Paper
DOI: 10.1039/C4OB00904E
Citation: Org. Biomol. Chem., 2014,12, 5158-5167
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    Synthesis and photophysical characterisation of new fluorescent triazole adenine analogues

    C. P. Lawson, A. Dierckx, F. Miannay, E. Wellner, L. M. Wilhelmsson and M. Grøtli, Org. Biomol. Chem., 2014, 12, 5158
    DOI: 10.1039/C4OB00904E

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