Synthesis and photophysical characterisation of new fluorescent triazole adenine analogues
Artikel i vetenskaplig tidskrift, 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

Författare

Christopher Lawson

Göteborgs universitet

Anke Dierckx

Chalmers, Kemi- och bioteknik, Fysikalisk kemi

Francois-Alexandre Miannay

Chalmers, Kemi- och bioteknik, Fysikalisk kemi

E. Wellner

AstraZeneca AB

Marcus Wilhelmsson

Chalmers, Kemi- och bioteknik, Fysikalisk kemi

Morten Grötli

Göteborgs universitet

Organic and Biomolecular Chemistry

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

Vol. 12 28 5158-5167

Styrkeområden

Nanovetenskap och nanoteknik

Livsvetenskaper och teknik

Ämneskategorier

Fysikalisk kemi

Organisk kemi

DOI

10.1039/c4ob00904e

Mer information

Senast uppdaterat

2018-04-18