Pentacyclic adenine: A versatile and exceptionally bright fluorescent DNA base analogue
Journal article, 2018

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 qA nitro , 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.

Author

Mattias Bood

University of Gothenburg

Anders Foller Füchtbauer

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry

Moa Sandberg Wranne

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Physical Chemistry

Jong Jin Ro

Pohang University of Science and Technology

Sangamesh Sarangamath

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Physical Chemistry

Afaf El-Sagheer

Suez University

Deborah Rupert

Chalmers, Physics, Biological Physics

Rachel S. Fisher

University of Edinburgh

Steven W. Magennis

University of Glasgow

Anita C. Jones

University of Edinburgh

Fredrik Höök

Chalmers, Physics, Biological Physics

T. Brown

University of Oxford

Byeang Hyean Kim

Pohang University of Science and Technology

Anders Dahlén

AstraZeneca AB

Marcus Wilhelmsson

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry

Morten Grötli

University of Gothenburg

Chemical Science

2041-6520 (ISSN) 2041-6539 (eISSN)

Vol. 9 14 3494-3502

Subject Categories

Atom and Molecular Physics and Optics

Other Physics Topics

Theoretical Chemistry

DOI

10.1039/c7sc05448c

More information

Latest update

4/18/2018