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Lighting Up DNA with the Environment-Sensitive Bright Adenine Analogue qAN4

Füchtbauer, Anders Foller, 1984 (author)
Göteborgs universitet,University of Gothenburg
Sandberg Wranne, Moa, 1986 (author)
Chalmers tekniska högskola,Chalmers University of Technology
Sarangamath, Sangamesh, 1992 (author)
Chalmers tekniska högskola,Chalmers University of Technology
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Bood, Mattias (author)
Gothenburg University,Göteborgs universitet,Institutionen för kemi och molekylärbiologi,Department of Chemistry and Molecular Biology,AstraZeneca AB,University of Gothenburg
El-Sagheer, A. H. (author)
University Of Oxford,Suez University
Brown, T. (author)
University Of Oxford
Grad?n, H. (author)
Grötli, Morten (author)
Gothenburg University,Göteborgs universitet,Institutionen för kemi och molekylärbiologi,Department of Chemistry and Molecular Biology,University of Gothenburg
Wilhelmsson, Marcus, 1974 (author)
Chalmers tekniska högskola,Chalmers University of Technology
Gradén, Henrik, 1968 (author)
AstraZeneca AB
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 (creator_code:org_t)
2020-02-11
2020
English.
In: Chempluschem. - : Wiley. - 2192-6506. ; 85:2, s. 319-326
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  • Journal article (peer-reviewed)
Abstract Subject headings
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  • The fluorescent adenine analogue qAN4 was recently shown to possess promising photophysical properties, including a high brightness as a monomer. Here we report the synthesis of the phosphoramidite of qAN4 and its successful incorporation into DNA oligonucleotides using standard solid-phase synthesis. Circular dichroism and thermal melting studies indicate that the qAN4-modification has a stabilizing effect on the B-form of DNA. Moreover, qAN4 base-pairs selectively with thymine with mismatch penalties similar to those of mismatches of adenine. The low energy absorption band of qAN4 inside DNA has its peak around 358 nm and the emission in duplex DNA is partly quenched and blue-shifted (ca. 410 nm), compared to the monomeric form. The spectral properties of the fluorophore also show sensitivity to pH; a property that may find biological applications. Quantum yields in single-stranded DNA range from 1-29 % and in duplex DNA from 1-7 %. In combination with the absorptive properties, this gives an average brightness inside duplex DNA of 275 M-1 cm(-1), more than five times higher than the most used environment-sensitive fluorescent base analogue, 2-aminopurine. Finally, we show that qAN4 can be used to advantage as a donor for interbase FRET applications in combination with adenine analogue qA(nitro) as an acceptor.

Subject headings

NATURVETENSKAP  -- Kemi (hsv//swe)
NATURAL SCIENCES  -- Chemical Sciences (hsv//eng)
NATURVETENSKAP  -- Kemi -- Polymerkemi (hsv//swe)
NATURAL SCIENCES  -- Chemical Sciences -- Polymer Chemistry (hsv//eng)
NATURVETENSKAP  -- Kemi -- Fysikalisk kemi (hsv//swe)
NATURAL SCIENCES  -- Chemical Sciences -- Physical Chemistry (hsv//eng)
NATURVETENSKAP  -- Fysik -- Atom- och molekylfysik och optik (hsv//swe)
NATURAL SCIENCES  -- Physical Sciences -- Atom and Molecular Physics and Optics (hsv//eng)

Keyword

base pairing
DNA
FRET
nucleobase analogues
photophysics
pteridine nucleoside analogs
base analog
fluorescence properties
quadracyclic adenine
energy-transfer
nucleic-acid
fret
spectroscopy
dynamics
nmr
Chemistry
nucleobase analogues

Publication and Content Type

ref (subject category)
art (subject category)

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