ArticleNucleic acids research2016
Efficient enzymatic synthesis and dual-colour fluorescent labelling of DNA probes using long chain azido-dUTP and BCN dyes.
Article in Nucleic acids research, 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.
- Highly efficient expression of DNA-peptide conjugates in growth-arrested cells.Nature communications · 2026Article
- Click Chemistry: Reaction Rates and Their Suitability for Biomedical Applications.Bioconjugate chemistry · 2024Review
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- Advanced preparation of fragment libraries enabled by oligonucleotide-modified 2',3'-dideoxynucleotides.Communications chemistry · 2022Article
- Internet of medical things-enabled CRISPR diagnostics for rapid detection of SARS-CoV-2 variants of concern.Frontiers in microbiology · 2022Article
- Expanding the chemical functionality of DNA nanomaterials generated by rolling circle amplification.Nucleic acids research · 2021Article
- 1,3-Diketone-Modified Nucleotides and DNA for Cross-Linking with Arginine-Containing Peptides and Proteins.Angewandte Chemie (International ed. in English) · 2021Article
- Nucleotide-Bearing Benzylidene-Tetrahydroxanthylium Near-IR Fluorophore for Sensing DNA Replication, Secondary Structures and Interactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Stable immobilization of aldehyde ketone reductase mutants containing nonstandard amino acids on an epoxy resinRSC advances · 2020Article
- Article
- dUTPs conjugated with zwitterionic Cy3 or Cy5 fluorophore analogues are effective substrates for DNA amplification and labelling by Taq polymerase.Nucleic acids research · 2018Article
- 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
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3 authors.
Funding
Abstract
A sterically undemanding azide analogue of dTTP (AHP dUTP) with an alkyl chain and ethynyl attachment to the nucleobase was designed and incorporated into DNA by primer extension, reverse transcription and polymerase chain reaction (PCR). An azide-modified 523 bp PCR amplicon with all 335 thymidines replaced by AHP dU was shown to be a perfect copy of the template from which it was amplified. Replacement of thymidine with AHP dU increases duplex stability, accounting in part for the high incorporation efficiency of the azide-modified triphosphate. Single-stranded azide-labelled DNA was conveniently prepared from PCR products by λ-exonuclease digestion and streptavidin magnetic bead isolation. Efficient fluorescent labelling of single and double-stranded DNA was carried out using dyes functionalized with bicyclo[6.1.0]non-4-yne (BCN) via the strain-promoted alkyne-azide cycloaddition (SPAAC) reaction. This revealed that the degree of labelling must be carefully controlled to achieve optimum fluorescence and avoid fluorescence quenching. Dual-coloured probes were obtained in a single tube fluorescent labelling reaction; and varying the ratios of the two dyes provides a simple method to prepare DNA probes with unique fluorescent signatures. AHP dUTP is a versatile clickable nucleotide with potentially wide applications in biology and nanotechnology including single molecule studies and synthesis of modified aptamer libraries via SELEX.
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