ArticleNucleic acids research2011
Highly fluorescent guanosine mimics for folding and energy transfer studies.
Article in Nucleic acids research, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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15 citing papers in PubMed, 64 citations in OpenAlex.
- Synthesis and Characterization of Fluorescence Active GChinese chemical letters = Zhongguo hua xue kuai bao · 2022Article
- Heterocycle-modified 2'-Deoxyguanosine Nucleolipid Analogs Stabilize Guanosine Gels and Self-assemble to Form Green Fluorescent Gels.Chemistry, an Asian journal · 2022Article
- Non-Canonical Helical Structure of Nucleic Acids Containing Base-Modified Nucleotides.International journal of molecular sciences · 2021Review
- Nucleic Acid Conformation Influences Postsynthetic Suzuki-Miyaura Labeling of Oligonucleotides.Bioconjugate chemistry · 2020Article
- Probing G-quadruplex topologies and recognition concurrently in real time and 3D using a dual-app nucleoside probe.Nucleic acids research · 2019Article
- A 5'-BODIPY End-label for Monitoring DNA Duplex-Quadruplex Exchange.Scientific reports · 2018Article
- Probing the competition between duplex and G-quadruplex/i-motif structures using a conformation-sensitive fluorescent nucleoside probe.Organic & biomolecular chemistry · 2018Article
- DNA as UV light-harvesting antenna.Nucleic acids research · 2018Article
- Fluorescent nucleobase analogues for base-base FRET in nucleic acids: synthesis, photophysics and applications.Beilstein journal of organic chemistry · 2018Review
- Fluorescence-based tools to probe G-quadruplexes in cell-free and cellular environments.RSC advances · 2018Article
- DNA Aptamer-Target Binding Motif Revealed Using a Fluorescent Guanine Probe: Implications for Food Toxin Detection.ACS omega · 2017Article
- In What Ways Do Synthetic Nucleotides and Natural Base Lesions Alter the Structural Stability of G-Quadruplex Nucleic Acids?Journal of nucleic acids · 2017Review
- C-Linked 8-aryl guanine nucleobase adducts: biological outcomes and utility as fluorescent probes.Chemical science · 2016Review
- The exception that confirms the rule: a higher-order telomeric G-quadruplex structure more stable in sodium than in potassium.Nucleic acids research · 2016Article
- Conformation-sensitive nucleoside analogues as topology-specific fluorescence turn-on probes for DNA and RNA G-quadruplexes.Nucleic acids research · 2015Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Guanosines with substituents at the 8-position can provide useful fluorescent probes that effectively mimic guanine residues even in highly demanding model systems such as polymorphic G-quadruplexes and duplex DNA. Here, we report the synthesis and photophysical properties of a small family of 8-substituted-2'-deoxyguanosines that have been incorporated into the human telomeric repeat sequence using phosphoramidite chemistry. These include 8-(2-pyridyl)-2'-deoxyguanosine (2PyG), 8-(2-phenylethenyl)-2'-deoxyguanosine (StG) and 8-[2-(pyrid-4-yl)-ethenyl]-2'-deoxyguanosine (4PVG). On DNA folding and stability, 8-substituted guanosines can exhibit context-dependent effects but were better tolerated by G-quadruplex and duplex structures than pyrimidine mismatches. In contrast to previously reported fluorescent guanine analogs, 8-substituted guanosines exhibit similar or even higher quantum yields upon their incorporation into nucleic acids (Φ = 0.02-0.45). We have used these highly emissive probes to quantify energy transfer efficiencies from unmodified DNA nucleobases to 8-substituted guanosines. The resulting DNA-to-probe energy transfer efficiencies (η(t)) are highly structure selective, with η(t)(duplex) < η(t)(single-strand) < η(t)(G-quadruplex). These trends were independent of the exact structural features and thermal stabilities of the G-quadruplexes or duplexes containing them. The combination of efficient energy transfer, high probe quantum yield, and high molar extinction coefficient of the DNA provides a highly sensitive and reliable readout of G-quadruplex formation even in highly diluted sample solutions of 0.25 nM.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.