ArticleScientific reports2015
Development of bright fluorescent quadracyclic adenine analogues: TDDFT-calculation supported rational design.
Article in Scientific reports, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Increased brightness of fluorescent uridine, qU, inside single- and double-stranded RNA.Scientific reports · 2026Article
- Fluorescent base analogues in gapmers enable stealth labeling of antisense oligonucleotide therapeutics.Scientific reports · 2021Article
- Getting DNA and RNA out of the dark with 2CNqA: a bright adenine analogue and interbase FRET donor.Nucleic acids research · 2020Article
- Flexibility and Preorganization of Fluorescent Nucleobase-Pyrene Conjugates Control DNA and RNA Recognition.Molecules (Basel, Switzerland) · 2020Article
- Electronic Modifications of Fluorescent Cytidine Analogues Control Photophysics and Fluorescent Responses to Base Stacking and Pairing.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
- Fluorescent nucleobase analogues for base-base FRET in nucleic acids: synthesis, photophysics and applications.Beilstein journal of organic chemistry · 2018Review
- Revealing Nucleic Acid Mutations Using Förster Resonance Energy Transfer-Based Probes.Sensors (Basel, Switzerland) · 2016Review
- Chromophoric Nucleoside Analogues: Synthesis and Characterization of 6-Aminouracil-Based Nucleodyes.The Journal of organic chemistry · 2016Article
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Authors and funding
9 authors.
Funding
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Abstract
Fluorescent base analogues (FBAs) comprise a family of increasingly important molecules for the investigation of nucleic acid structure and dynamics. We recently reported the quantum chemical calculation supported development of four microenvironment sensitive analogues of the quadracyclic adenine (qA) scaffold, the qANs, with highly promising absorptive and fluorescence properties that were very well predicted by TDDFT calculations. Herein, we report on the efficient synthesis, experimental and theoretical characterization of nine novel quadracyclic adenine derivatives. The brightest derivative, 2-CNqA, displays a 13-fold increased brightness (εΦF = 4500) compared with the parent compound qA and has the additional benefit of being a virtually microenvironment-insensitive fluorophore, making it a suitable candidate for nucleic acid incorporation and use in quantitative FRET and anisotropy experiments. TDDFT calculations, conducted on the nine novel qAs a posteriori, successfully describe the relative fluorescence quantum yield and brightness of all qA derivatives. This observation suggests that the TDDFT-based rational design strategy may be employed for the development of bright fluorophores built up from a common scaffold to reduce the otherwise costly and time-consuming screening process usually required to obtain useful and bright FBAs.
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