ArticleChemistry (Weinheim an der Bergstrasse, Germany)2016
Trianguleniums as Optical Probes for G-Quadruplexes: A Photophysical, Electrochemical, and Computational Study.
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 17 papers.
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17 citing papers in PubMed, 35 citations in OpenAlex.
- Breaking the limit - synthesis and properties ofChemical science · 2026Article
- Lifetime chemical sensor arrays of organic fluorophores for bacterial fingerprinting.Nature communications · 2026Article
- Chemical fluorophores for fluorescence lifetime imaging.Chemical Society reviews · 2026Review
- Microwave-assisted synthesis of new triangulenium dyes for lifetime imaging microscopy (FLIM).Scientific reports · 2025Article
- Molecular Rotors: Fluorescent Sensors for Microviscosity and Conformation of Biomolecules.Angewandte Chemie (International ed. in English) · 2024Review
- Anion-dependent ion-pairing assemblies of triazatriangulenium cation that interferes with stacking structures.Beilstein journal of organic chemistry · 2024Article
- Selective, Disruptive Luminescent Ru(II) Polypyridyl Probes of G-Quadruplex.Inorganic chemistry · 2023Article
- Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds.Chemical reviews · 2022Review
- Cationic helicenes as selective G4 DNA binders and optical probes for cellular imaging.Chemical science · 2021Article
- DNA Binding Mode Analysis of a Core-Extended Naphthalene Diimide as a Conformation-Sensitive Fluorescent Probe of G-Quadruplex Structures.International journal of molecular sciences · 2021Article
- Trioxatriangulenium (TOTAChemical science · 2021Article
- Visualising G-quadruplex DNA dynamics in live cells by fluorescence lifetime imaging microscopy.Nature communications · 2021Article
- The cytotoxic potential of cationic triangulenes against tumour cells.MedChemComm · 2019Article
- Selectivity of Terpyridine Platinum Anticancer Drugs for G-quadruplex DNA.Molecules (Basel, Switzerland) · 2019Article
- C-Functionalized Cationic Diazaoxatriangulenes: Late-Stage Synthesis and Tuning of Physicochemical Properties.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
- Azadioxatriangulenium and Diazaoxatriangulenium: Quantum Yields and Fundamental Photophysical Properties.ACS omega · 2017Article
- Trianguleniums as Optical Probes for G-Quadruplexes: A Photophysical, Electrochemical, and Computational Study.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
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Authors and funding
6 authors at 1 institution in 1 country.
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No grant is acknowledged in the PubMed record.
Abstract
Nucleic acids can adopt non-duplex topologies, such as G-quadruplexes in vitro. Yet it has been challenging to establish their existence and function in vivo due to a lack of suitable tools. Recently, we identified the triangulenium compound DAOTA-M2 as a unique fluorescence probe for such studies. This probe's emission lifetime is highly dependent on the topology of the DNA it interacts with opening up the possibility of carrying out live-cell imaging studies. Herein, we describe the origin of its fluorescence selectivity for G-quadruplexes. Cyclic voltammetry predicts that the appended morpholino groups can act as intra- molecular photo-induced electron transfer (PET) quenchers. Photophysical studies show that a delicate balance between this effect and inter-molecular PET with nucleobases is key to the overall fluorescence enhancement observed upon nucleic acid binding. We utilised computational modelling to demonstrate a conformational dependence of intra-molecular PET. Finally, we performed orthogonal studies with a triangulenium compound, in which the morpholino groups were removed, and demonstrated that this change inverts triangulenium fluorescence selectivity from G-quadruplex to duplex DNA, thus highlighting the importance of fine tuning the molecular structure not only for target affinity, but also for fluorescence response.
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