ArticleNature protocols2011
Preparation of 18F-labeled peptides using the copper(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition.
Article in Nature protocols, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed, 46 citations in OpenAlex.
- Synthesis and preclinical evaluation of gastrin releasing peptide receptor antagonist [EJNMMI radiopharmacy and chemistry · 2025Article
- Hetero-Diels-Alder and CuAAC Click Reactions for Fluorine-18 Labeling of Peptides: Automation and Comparative Study of the Two Methods.Molecules (Basel, Switzerland) · 2024Article
- A proof-of-concept study on the use of a fluorescein-basedEJNMMI radiopharmacy and chemistry · 2022Article
- Lipophilicity and Click Reactivity Determine the Performance of Bioorthogonal Tetrazine Tools in PretargetedACS pharmacology & translational science · 2021Article
- Convenient Entry toEuropean journal of organic chemistry · 2019Article
- Review
- Polyglucose nanoparticles with renal elimination and macrophage avidity facilitate PET imaging in ischaemic heart disease.Nature communications · 2017Article
- Rapid, high efficiency isolation of pancreatic ß-cells.Scientific reports · 2015Article
- Fluorine-18 radiochemistry, labeling strategies and synthetic routes.Bioconjugate chemistry · 2015Review
- Fluorescent exendin-4 derivatives for pancreatic β-cell analysis.Bioconjugate chemistry · 2014Article
- Using 5-deoxy-5-[18F]fluororibose to glycosylate peptides for positron emission tomography.Nature protocols · 2014Article
- 18F-labeling using click cycloadditions.BioMed research international · 2014Review
- Pretargeted imaging and radioimmunotherapy of cancer using antibodies and bioorthogonal chemistry.Frontiers in medicine · 2014Review
- Peptide conjugation via CuAAC 'click' chemistry.Molecules (Basel, Switzerland) · 2013Article
- Positron emission tomography imaging of drug-induced tumor apoptosis with a caspase-triggered nanoaggregation probe.Angewandte Chemie (International ed. in English) · 2013Article
- Enhanced aqueous Suzuki-Miyaura coupling allows site-specific polypeptide 18F-labeling.Journal of the American Chemical Society · 2013Article
- Recent trends in bioorthogonal click-radiolabeling reactions using fluorine-18.Molecules (Basel, Switzerland) · 2013Review
- Chelator-accelerated one-pot 'click' labeling of small molecule tracers with 2-[¹⁸F]fluoroethyl azide.Molecules (Basel, Switzerland) · 2013Article
- One-step (18)F-labeling of peptides for positron emission tomography imaging using the SiFA methodology.Nature protocols · 2012Article
- Efficient method for site-specific 18F-labeling of biomolecules using the rapid condensation reaction between 2-cyanobenzothiazole and cysteine.Bioconjugate chemistry · 2012Article
Corrections and comments
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Authors and funding
2 authors at 1 institution.
Funding
No grant is acknowledged in the PubMed record.
Abstract
An optimized procedure for preparing fluorine-18 ((18)F)-labeled peptides by the copper-catalyzed azide-alkyne 1,3-dipolar cyloaddition (CuAAC) is presented here. The two-step radiosynthesis begins with the microwave-assisted nucleophilic (18)F-fluorination of a precursor containing a terminal p-toluenesulfonyl, terminal azide and polyethylene glycol backbone. The resulting (18)F-fluorinated azide-containing building block is coupled to an alkyne-decorated peptide by the CuAAC. The reaction is accelerated by the copper(I)-stabilizing ligand bathophenanthroline disulfonate and can be performed in either reducing or nonreducing conditions (e.g., to preserve disulfide bonds). After an HPLC purification, (18)F-labeled peptide can be obtained with a 31 ± 6% radiochemical yield (n = 4, decay-corrected from (18)F-fluoride elution) and a specific activity of 39.0 ± 12.4 Ci μmol(-1) within 77 ± 4 min.
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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.