ArticleNucleic acids research2015
Xanthine and 8-oxoguanine in G-quadruplexes: formation of a G·G·X·O tetrad.
Article in Nucleic acids research, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed.
- Function-preserving photooxidation of AS1411 aptamer by a G-quadruplex-guided photosensitizer.Chemical science · 2026Article
- G-quadruplex DNA reprograms the photochemistry of CX-5461 toward radical-driven anticancer activity.Nucleic acids research · 2026Article
- 8-Oxoguanine Forms Quartets with a Large Central Cavity.Biochemistry · 2022Article
- Epigenomic features of DNA G-quadruplexes and their roles in regulating rice gene transcription.Plant physiology · 2022Article
- Essential Roles and Risks of G-Quadruplex Regulation: Recognition Targets of ALS-Linked TDP-43 and FUS.Frontiers in molecular biosciences · 2022Review
- Interrogating accessibility of telomeric sequences with FRET-PAINT: evidence for length-dependent telomere compaction.Nucleic acids research · 2021Article
- Roles for the 8-Oxoguanine DNA Repair System in Protecting Telomeres From Oxidative Stress.Frontiers in cell and developmental biology · 2021Review
- Position-Dependent Effect of Guanine Base Damage and Mutations on Telomeric G-Quadruplex and Telomerase Extension.Biochemistry · 2020Article
- Analytical and Structural Studies for the Investigation of Oxidative Stress in Guanine Oligonucleotides.International journal of molecular sciences · 2020Review
- Self-assembling purine and pteridine quartets: how do π-conjugation patterns affect resonance-assisted hydrogen bonding?Organic & biomolecular chemistry · 2020Article
- The Structure and Function of DNA G-Quadruplexes.Trends in chemistry · 2020Review
- Fundamentals of G-quadruplex biology.Annual reports in medicinal chemistry · 2020Article
- Impact of Oxidative Lesions on the Human Telomeric G-Quadruplex.Journal of the American Chemical Society · 2019Article
- Promise of G-Quadruplex Structure Binding Ligands as Epigenetic Modifiers with Anti-Cancer Effects.Molecules (Basel, Switzerland) · 2019Review
- Non-duplex G-Quadruplex Structures Emerge as Mediators of Epigenetic Modifications.Trends in genetics : TIG · 2019Review
- Mixed guanine, adenine base quartets: possible roles of protons and metal ions in their stabilization.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2018Article
- Molecular mechanisms by which oxidative DNA damage promotes telomerase activity.Nucleic acids research · 2017Article
- Ball with hair: modular functionalization of highly stable G-quadruplex DNA nano-scaffolds through N2-guanine modification.Nucleic acids research · 2017Article
- Clustered abasic lesions profoundly change the structure and stability of human telomeric G-quadruplexes.Nucleic acids research · 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
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Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
G-quadruplexes are four-stranded structures built from stacked G-tetrads (G·G·G·G), which are planar cyclical assemblies of four guanine bases interacting through Hoogsteen hydrogen bonds. A G-quadruplex containing a single guanine analog substitution, such as 8-oxoguanine (O) or xanthine (X), would suffer from a loss of a Hoogsteen hydrogen bond within a G-tetrad and/or potential steric hindrance. We show that a proper arrangement of O and X bases can reestablish the hydrogen-bond pattern within a G·G·X·O tetrad. Rational incorporation of G·G·X·O tetrads in a (3+1) G-quadruplex demonstrated a similar folding topology and thermal stability to that of the unmodified G-quadruplex. pH titration conducted on X·O-modified G-quadruplexes indicated a protonation-deprotonation equilibrium of X with a pKa ∼6.7. The solution structure of a G-quadruplex containing a G·G·X·O tetrad was determined, displaying the same folding topology in both the protonated and deprotonated states. A G-quadruplex containing a deprotonated X·O pair was shown to exhibit a more electronegative groove compared to that of the unmodified one. These differences are likely to manifest in the electronic properties of G-quadruplexes and may have important implications for drug targeting and DNA-protein interactions.
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