Synthesis and photophysical characterisation of new fluorescent triazole adenine analogues
Journal article, 2014

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.

PROBES

OLIGONUCLEOTIDES

NUCLEOSIDE ANALOGS

DNA-BASE ANALOG

CONFORMATION

PYRROLO-DC

HYBRIDIZATION

CLICK CHEMISTRY

DUPLEX

NUCLEIC-ACID

Author

Christopher Lawson

University of Gothenburg

Anke Dierckx

Chalmers, Chemical and Biological Engineering, Physical Chemistry

Francois-Alexandre Miannay

Chalmers, Chemical and Biological Engineering, Physical Chemistry

E. Wellner

AstraZeneca AB

Marcus Wilhelmsson

Chalmers, Chemical and Biological Engineering, Physical Chemistry

Morten Grötli

University of Gothenburg

Organic and Biomolecular Chemistry

1477-0520 (ISSN) 1477-0539 (eISSN)

Vol. 12 28 5158-5167

Areas of Advance

Nanoscience and Nanotechnology (2010-2017)

Life Science Engineering (2010-2018)

Subject Categories

Physical Chemistry

Organic Chemistry

DOI

10.1039/c4ob00904e

More information

Latest update

4/18/2018