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Issue 14, 2018

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

Author affiliations

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 Förster 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 cholesterol-anchored 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.

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

Supplementary files

Article information


Submitted
23 Dec 2017
Accepted
01 Mar 2018
First published
01 Mar 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 3494-3502
Article type
Edge Article

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

M. Bood, A. F. Füchtbauer, 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. Höök, T. Brown, B. H. Kim, A. Dahlén, L. M. Wilhelmsson and M. Grøtli, Chem. Sci., 2018, 9, 3494 DOI: 10.1039/C7SC05448C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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