ArticleChemical science2015
Azidophenyl as a click-transformable redox label of DNA suitable for electrochemical detection of DNA-protein interactions.
Article in Chemical science, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 59 citations in OpenAlex.
- Nitrogen-Centered Radicals Derived from Azidonucleosides.Molecules (Basel, Switzerland) · 2024Review
- Normalized Multipotential Redox Coding of DNA Bases for Determination of Total Nucleotide Composition.Analytical chemistry · 2023Article
- Advanced preparation of fragment libraries enabled by oligonucleotide-modified 2',3'-dideoxynucleotides.Communications chemistry · 2022Article
- Tuning of Oxidation Potential of Ferrocene for Ratiometric Redox Labeling and Coding of Nucleotides and DNA.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Determination of hypoxia-inducible factor-1 by using a ratiometric colorimetric test based on click-mediated growth of gold nanoparticles.Mikrochimica acta · 2018Article
- Article
- 2-Substituted dATP Derivatives as Building Blocks for Polymerase-Catalyzed Synthesis of DNA Modified in the Minor Groove.Angewandte Chemie (International ed. in English) · 2016Article
- Efficient enzymatic synthesis and dual-colour fluorescent labelling of DNA probes using long chain azido-dUTP and BCN dyes.Nucleic acids research · 2016Article
Corrections and comments
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Authors and funding
7 authors at 4 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
New redox labelling of DNA by an azido group which can be chemically transformed to nitrophenyltriazole or silenced to phenyltriazole was developed and applied to the electrochemical detection of DNA-protein interactions. 5-(4-Azidophenyl)-2'-deoxycytidine and 7-(4-azidophenyl)-7-deaza-2'-deoxyadenosine nucleosides were prepared by aqueous-phase Suzuki cross-coupling and converted to nucleoside triphosphates (dNTPs) which served as substrates for incorporation into DNA by DNA polymerase. The azidophenyl-modified nucleotides and azidophenyl-modified DNA gave a strong signal in voltammetric studies, at -0.9 V, due to reduction of the azido function. The Cu-catalyzed click reaction of azidophenyl-modified nucleosides or azidophenyl-modified DNA with 4-nitrophenylacetylene gave nitrophenyl-substituted triazoles, exerting a reduction peak at -0.4 V under voltammetry, whereas the click reaction with phenylacetylene gave electrochemically silent phenyltriazoles. The transformation of the azidophenyl label to nitrophenyltriazole was used for electrochemical detection of DNA-protein interactions (p53 protein) since only those azidophenyl groups in the parts of the DNA not shielded by the bound p53 protein were transformed to nitrophenyltriazoles, whereas those covered by the protein were not.
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Registered trials
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