ArticleBioconjugate chemistry2015
Strain Promoted Click Chemistry of 2- or 8-Azidopurine and 5-Azidopyrimidine Nucleosides and 8-Azidoadenosine Triphosphate with Cyclooctynes. Application to Living Cell Fluorescent Imaging.
Article in Bioconjugate chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 60 citations in OpenAlex.
- A Water-Soluble Fluorogenic Probe to Quantify Azide Concentrations in Biologically Relevant Environments.Biomacromolecules · 2026Article
- Bioorthogonal Chemistry in Biomolecule Quantification: A Review of Reactions and Strategies.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- A Fluorogenic Hydrazino-Pictet-Spengler Reaction in Live Cells.Angewandte Chemie (International ed. in English) · 2025Article
- Microwave-assisted synthesis of base-modified fluorescent 1,4-dihydropyridine nucleosides: photophysical characterization and insights.RSC advances · 2024Article
- Nitrogen-Centered Radicals Derived from Azidonucleosides.Molecules (Basel, Switzerland) · 2024Review
- LDLR-Mediated Targeting and Productive Uptake of siRNA-Peptide Ligand Conjugates In Vitro and In Vivo.Pharmaceutics · 2024Article
- Fluorogenic Reactions in Chemical Biology: Seeing Chemistry in Cells.Chemical & biomedical imaging · 2023Review
- 4-Azidocinnoline-Cinnoline-4-amine Pair as a New Fluorogenic and Fluorochromic Environment-Sensitive Probe.Molecules (Basel, Switzerland) · 2021Article
- Traceless Click-Assisted Native Chemical Ligation Enabled by Protecting Dibenzocyclooctyne from Acid-Mediated Rearrangement with Copper(I).Bioconjugate chemistry · 2021Article
- Modified Nucleosides, Nucleotides and Nucleic Acids via Click Azide-Alkyne Cycloaddition for Pharmacological Applications.Molecules (Basel, Switzerland) · 2021Review
- 1,2,3-Triazoles as leaving groups: SBeilstein journal of organic chemistry · 2021Article
- 1,2,3-Triazoles as leaving groups in SBeilstein journal of organic chemistry · 2021Article
- Synthesis and Properties of 6-Aryl-4-azidocinnolines and 6-Aryl-4-(1,2,3-1Molecules (Basel, Switzerland) · 2019Article
- Fluorescent 5-Pyrimidine and 8-Purine Nucleosides Modified with an N-Unsubstituted 1,2,3-Triazol-4-yl Moiety.The Journal of organic chemistry · 2019Article
- Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines.Beilstein journal of organic chemistry · 2019Article
- Electron-Mediated Aminyl and Iminyl Radicals from C5 Azido-Modified Pyrimidine Nucleosides Augment Radiation Damage to Cancer Cells.Organic letters · 2018Article
- Article
- Modern Synthetic Avenues for the Preparation of Functional Fluorophores.Angewandte Chemie (International ed. in English) · 2017Review
- Synthesis of 8-(1,2,3-triazol-1-yl)-7-deazapurine nucleosides by azide-alkyne click reactions and direct C-H bond functionalization.Tetrahedron letters · 2016Article
- Non-Catalyzed Click Reactions of ADIBO Derivatives with 5-Methyluridine Azides and Conformational Study of the Resulting Triazoles.PloS one · 2015Article
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Authors and funding
9 authors at 1 institution in 1 country.
Funding
Abstract
Strain-promoted click chemistry of nucleosides and nucleotides with an azido group directly attached to the purine and pyrimidine rings with various cyclooctynes in aqueous solution at ambient temperature resulted in efficient formation (3 min to 3 h) of fluorescent, light-up, triazole products. The 2- and 8-azidoadenine nucleosides reacted with fused cyclopropyl cyclooctyne, dibenzylcyclooctyne, or monofluorocyclooctyne to produce click products functionalized with hydroxyl, amino, N-hydroxysuccinimide, or biotin moieties. The 5-azidouridine and 5-azido-2'-deoxyuridine were similarly converted to the analogous triazole products in quantitative yields in less than 5 min. The 8-azido-ATP quantitatively afforded the triazole product with fused cyclopropyl cyclooctyne in aqueous acetonitrile (3 h). The novel triazole adducts at the 2- or 8-position of adenine or 5-position of uracil rings induce fluorescence properties which were used for direct imaging in MCF-7 cancer cells without the need for traditional fluorogenic reporters. FLIM of the triazole click adducts demonstrated their potential utility for dynamic measuring and tracking of signaling events inside single living cancer cells.
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