ArticleChemistry (Weinheim an der Bergstrasse, Germany)2016
A Water-Soluble Tetraazaperopyrene Dye as Strong G-Quadruplex DNA Binder.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 40 citations in OpenAlex.
- DNA-Binding Properties of Iridium(III) Complexes Encompassing Design, Function and Biophysical Assessments.Chemphyschem : a European journal of chemical physics and physical chemistry · 2026Review
- Twisted 1- and 2-Azaperopyrenes: Synthesis, Structure, and Properties.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Bridged Azobenzene Exhibits Fully Reversible Photocontrolled Binding to a G‑Quadruplex DNA/Duplex Junction.JACS Au · 2025Article
- DNA-Binding Properties of Non-Intercalating Water-Soluble Organometallic Ir(III) Luminophores.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Peri-Functionalized Tetraazaperylenes: Strong Emitters for Molecular Polaritonics.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Piperine analogs arrest c-myc gene leading to downregulation of transcription for targeting cancer.Scientific reports · 2021Article
- Stiff-Stilbene Ligands Target G-Quadruplex DNA and Exhibit Selective Anticancer and Antiparasitic Activity.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Small Sequence-Sensitive Compounds for Specific Recognition of the G⋅C Base Pair in DNA Minor Groove.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Targeted cell imaging properties of a deep red luminescent iridium(iii) complex conjugated with a c-Myc signal peptide.Chemical science · 2020Article
- Importance of Chiral Recognition in Designing Metal-Free Ligands for G-Quadruplex DNA.Molecules (Basel, Switzerland) · 2019Article
- The Thiophene "Sigma-Hole" as a Concept for Preorganized, Specific Recognition of G⋅C Base Pairs in the DNA Minor Groove.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
- A Water-Soluble Tetraazaperopyrene Dye as Strong G-Quadruplex DNA Binder.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
Corrections and comments
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Authors and funding
3 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The interactions of the water-soluble tetraazaperopyrene dye 1 with ct-DNA, duplex-[(dAdT)12 ⋅(dAdT)12 ], duplex-[(dGdC)12 ⋅(dGdC)12 ] as well as with two G-quadruplex-forming sequences, namely the human telomeric 22AG and the promotor sequence c-myc, were investigated by means of UV/visible and fluorescence spectroscopy, isothermal titration calorimetry (ITC) and molecular docking studies. Dye 1 exhibits a high affinity for G-quadruplex structures over duplex DNA structures. Furthermore, the ligand shows promising G-quadruplex discrimination, with an affinity towards c-myc of 2×10(7) m(-1) (i.e., Kd =50 nm), which is higher than for 22AG (4×10(6) m(-1) ). The ITC data reveal that compound 1 interacts with c-myc in a stoichiometric ratio of 1:1 but also indicate the presence of two identical lower affinity secondary binding sites per quadruplex. In 22AG, there are two high affinity binding sites per quadruplex, that is, one on each side, with a further four weaker binding sites. For both quadruplex structures, the high affinity interactions between compound 1 and the quadruplex-forming nucleic acid structures are weakly endothermic. Molecular docking studies suggest an end-stacking binding mode for compound 1 interacting with quadruplex structures, and a higher affinity for the parallel conformation of c-myc than for the mixed-hybrid conformation of 22AG. In addition, docking studies also suggest that the reduced affinity for duplex DNA structures is due to the non-viability of an intercalative binding mode.
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Registered trials
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.