ArticleJournal of the American Chemical Society2015
Conquering 2-aminopurine's deficiencies: highly emissive isomorphic guanosine surrogate faithfully monitors guanosine conformation and dynamics in DNA.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed, 76 citations in OpenAlex.
- New insights into the structure and dynamics of the epigenetic modifications on DNA.RSC chemical biology · 2025Article
- Decoding the base flipping mechanism of the SET- and RING-associated (SRA) domain of the epigenetic UHRF1 protein.Nucleic acids research · 2025Article
- Impacts of sequence and structure on pyrrolocytosine fluorescence in RNA.Nucleic acids research · 2025Article
- Template-independent enzymatic functionalization of DNA oligonucleotides with environment-sensitive nucleotide probes using terminal deoxynucleotidyl transferase.Nucleic acids research · 2025Article
- Isomorphic Fluorescent Nucleosides.Accounts of chemical research · 2024Article
- Thieno[3,4-Chemical science · 2023Article
- CRISPR-Cas9 recognition of enzymatically synthesized base-modified nucleic acids.Nucleic acids research · 2023Article
- Single-molecule fluorescence detection of a tricyclic nucleoside analogue.Chemical science · 2020Article
- What Makes Thienoguanosine an Outstanding Fluorescent DNA Probe?Journal of the American Chemical Society · 2020Article
- Deciphering the pH-dependence of ground- and excited-state equilibria of thienoguanine.Physical chemistry chemical physics : PCCP · 2020Article
- Probing of Nucleic Acid Structures, Dynamics, and Interactions With Environment-Sensitive Fluorescent Labels.Frontiers in chemistry · 2020Review
- 4-Cyanoindole-2'-deoxyribonucleoside (4CIN): A Universal Fluorescent Nucleoside Analogue.Organic letters · 2018Article
- Fluorescent RNA cytosine analogue - an internal probe for detailed structure and dynamics investigations.Scientific reports · 2017Article
- Expanding a fluorescent RNA alphabet: synthesis, photophysics and utility of isothiazole-derived purine nucleoside surrogates.Chemical science · 2017Article
- Dynamics of Methylated Cytosine Flipping by UHRF1.Journal of the American Chemical Society · 2017Article
- Polymerase-Mediated Site-Specific Incorporation of a Synthetic Fluorescent Isomorphic G Surrogate into RNA.Angewandte Chemie (International ed. in English) · 2017Article
- Solvatochromic fluorene-linked nucleoside and DNA as color-changing fluorescent probes for sensing interactions.Chemical science · 2016Article
- Tautomers of a Fluorescent G Surrogate and Their Distinct Photophysics Provide Additional Information Channels.Angewandte Chemie (International ed. in English) · 2016Article
- Chromophoric Nucleoside Analogues: Synthesis and Characterization of 6-Aminouracil-Based Nucleodyes.The Journal of organic chemistry · 2016Article
- Quantitative sampling of conformational heterogeneity of a DNA hairpin using molecular dynamics simulations and ultrafast fluorescence spectroscopy.Nucleic acids research · 2016Article
Corrections and comments
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Authors and funding
7 authors at 6 institutions in 4 countries.
Funding
Abstract
The archetypical fluorescent nucleoside analog, 2-aminopurine (2Ap), has been used in countless assays, though it suffers from very low quantum yield, especially when included in double strands, and from the fact that its residual emission frequently does not represent biologically relevant conformations. To conquer 2Ap's deficiencies, deoxythienoguanosine (d(th)G) was recently developed. Here, steady-state and time-resolved fluorescence spectroscopy was used to compare the ability of 2Ap and d(th)G, to substitute and provide relevant structural and dynamical information on a key G residue in the (-) DNA copy of the HIV-1 primer binding site, (-)PBS, both in its stem loop conformation and in the corresponding (-)/(+)PBS duplex. In contrast to 2Ap, this fluorescent nucleoside when included in (-)PBS or (-)/(+)PBS duplex fully preserves their stability and exhibits a respectable quantum yield and a simple fluorescence decay, with marginal amounts of dark species. In further contrast to 2Ap, the fluorescently detected d(th)G species reflect the predominantly populated G conformers, which allows exploring their relevant dynamics. Being able to perfectly substitute G residues, d(th)G will transform nucleic acid biophysics by allowing, for the first time, to selectively and faithfully monitor the conformations and dynamics of a given G residue in a DNA sequence.
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