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Pentacyclic adenine: a versatile and exceptionally bright fluorescent DNA base analogue

Journal article
Authors Mattias Bood
A. F. Fuchtbauer
M. S. Wranne
J. J. Ro
S. Sarangamath
A. H. El-Sagheer
D. L. M. Rupert
R. S. Fisher
S. W. Magennis
A. C. Jones
F. Hook
T. Brown
B. H. Kim
A. Dahlen
L. M. Wilhelmsson
Morten Grötli
Published in Chemical Science
Volume 9
Issue 14
Pages 3494-3502
ISSN 2041-6520
Publication year 2018
Published at Department of Chemistry and Molecular Biology
Pages 3494-3502
Language en
Links doi.org/10.1039/c7sc05448c
Keywords pteridine nucleoside analogs, emissive rna alphabet, 2-photon, excitation, nucleic-acid, quadracyclic adenine, nucleobase analogs, tc, 2-aminopurine, nucleotides, environment
Subject categories Chemical Sciences

Abstract

Emissive base analogs are powerful tools for probing nucleic acids at the molecular level. Herein we describe the development and thorough characterization of pentacyclic adenine (pA), a versatile base analog with exceptional fluorescence properties. When incorporated into DNA, pA pairs selectively with thymine without perturbing the B-form structure and is among the brightest nucleobase analogs reported so far. Together with the recently established base analog acceptor qAnitro, pA allows accurate distance and orientation determination via Forster resonance energy transfer (FRET) measurements. The high brightness at emission wavelengths above 400 nm also makes it suitable for fluorescence microscopy, as demonstrated by imaging of single liposomal constructs coated with cholesterolanchored pA-dsDNA, using total internal reflection fluorescence microscopy. Finally, pA is also highly promising for two-photon excitation at 780 nm, with a brightness (5.3 GM) that is unprecedented for a base analog.

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