ArticleBioconjugate chemistry2011
Strain-promoted "click" chemistry for terminal labeling of DNA.
Article in Bioconjugate chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed, 80 citations in OpenAlex.
- Development of a highly sensitive photometric readout platform technology using SPAAC-modified HRP liposomes.Analytical and bioanalytical chemistry · 2026Article
- Recent Advances in Conjugation Chemistry Expanding the Applications of the DNA Tetrahedron.Chemical biology & drug design · 2026Review
- Oligonucleotides Post-Synthetic Modifications: An Overview of Clickable Nucleoside Phosphoramidites Suitable for Solid-Phase Synthesis.Chembiochem : a European journal of chemical biology · 2026Review
- Bioorthogonal Chemistry in Biomolecule Quantification: A Review of Reactions and Strategies.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- Reactivity Profiling for High-Yielding Ynamine-Tagged Oligonucleotide Click Chemistry Bioconjugations.Bioconjugate chemistry · 2024Article
- Faster Surface Ligation Reactions Improve Immobilized Enzyme Structure and Activity.Journal of the American Chemical Society · 2021Article
- Enhancing MicroRNA Activity through Increased Endosomal Release Mediated by Nigericin.Molecular therapy. Nucleic acids · 2019Article
- Practical Considerations, Challenges, and Limitations of Bioconjugation via Azide-Alkyne Cycloaddition.Bioconjugate chemistry · 2018Review
- FolamiRs: Ligand-targeted, vehicle-free delivery of microRNAs for the treatment of cancer.Science translational medicine · 2017Article
- 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
- Evolution of thermophilic DNA polymerases for the recognition and amplification of C2'-modified DNA.Nature chemistry · 2016Article
- Nucleotidyl transferase assisted DNA labeling with different click chemistries.Nucleic acids research · 2015Article
- Designing Dendrimer and Miktoarm Polymer Based Multi-Tasking Nanocarriers for Efficient Medical Therapy.Molecules (Basel, Switzerland) · 2015Review
- 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.Bioconjugate chemistry · 2015Article
- Alkyne-azide "click" chemistry in designing nanocarriers for applications in biology.Molecules (Basel, Switzerland) · 2013Review
- Oligonucleotide tagging for copper-free click conjugation.Molecules (Basel, Switzerland) · 2013Article
- Post-assembly functionalization of organoplatinum(II) metallacycles via copper-free click chemistry.Journal of the American Chemical Society · 2012Article
- Covalent protein-oligonucleotide conjugates by copper-free click reaction.Bioorganic & medicinal chemistry · 2012Article
- Site-specific terminal and internal labeling of RNA by poly(A) polymerase tailing and copper-catalyzed or copper-free strain-promoted click chemistry.Nucleic acids research · 2012Article
Corrections and comments
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
Abstract
1,3-Dipolar [3 + 2] cycloaddition between azides and alkynes--an archetypal "click" chemistry--has been used increasingly for the functionalization of nucleic acids. Copper(I)-catalyzed 1,3-dipolar cycloaddition reactions between alkyne-tagged DNA molecules and azides work well, but they require optimization of multiple reagents, and Cu ions are known to mediate DNA cleavage. For many applications, it would be preferable to eliminate the Cu(I) catalyst from these reactions. Here, we describe the solid-phase synthesis and characterization of 5'-dibenzocyclooctyne (DIBO)-modified oligonucleotides, using a new DIBO phosphoramidite, which react with azides via copper-free, strain-promoted alkyne-azide cycloaddition (SPAAC). We found that the DIBO group not only survived the standard acidic and oxidative reactions of solid-phase oligonucleotide synthesis (SPOS), but that it also survived the thermal cycling and standard conditions of the polymerase chain reaction (PCR). As a result, PCR with DIBO-modified primers yielded "clickable" amplicons that could be tagged with azide-modified fluorophores or immobilized on azide-modified surfaces. Given its simplicity, SPAAC on DNA could streamline the bioconjugate chemistry of nucleic acids in a number of modern biotechnologies.
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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.