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

Mattias Bood, Anders F. Füchtbauer, Moa S. Wranne, Jong Jin Ro, Sangamesh Sarangamath, Afaf H. El-sagheer, Déborah L. M. Rupert, Rachel S. Fisher, Steven W. Magennis, Anita C. Jones, Fredrik Höök, Tom Brown, Byeang Hyean Kim, Anders Dahlén, L. Marcus Wilhelmsson, Morten Grøtli

Research output: Contribution to journalArticlepeer-review

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.
Original languageEnglish
Pages (from-to)3494-3502
Number of pages9
JournalChemical Science
Volume9
Issue number14
Early online date1 Mar 2018
DOIs
Publication statusPublished - 14 Apr 2018

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