ReviewChemical reviews2017
Oximes and Hydrazones in Bioconjugation: Mechanism and Catalysis.
Review in Chemical reviews, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 221 papers.
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Who cites it
221 citing papers in PubMed.
- Post-fabrication reconfiguration of hydrogels through thermodynamic asymmetry in dynamic chemistry.Nature communications · 2026Article
- Synthesis and molecular characterization of a novel FA-ADH-GMS conjugated pH-responsive lipid for targeted drug delivery.Molecular diversity · 2026Article
- Harnessing Vinyl Cation Reactivity Enables Oxime Ether Formation and an Unusual Base-Promoted Rearrangement to Esters.JACS Au · 2026Article
- Organocatalytically-Tuned In Situ Formed Alginate Hydrogel Enables Sustained Therapeutic Release.Chemistry, an Asian journal · 2026Article
- A Chemical Framework for Engineering Extracellular Vesicles' Biointerface to Advance Precision Therapeutics.Advanced materials (Deerfield Beach, Fla.) · 2026Review
- Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides by a Covalent Catch-and-Release Approach.Angewandte Chemie (International ed. in English) · 2026Article
- Dynamic Covalent Functionalization of DNA Origami via Iminoboronate Chemistry.Journal of the American Chemical Society · 2026Article
- Fluorescent Probes for Aldehyde Detection in Biological Systems: Design Principles, Spectroscopy, and Emerging Applications.Sensors (Basel, Switzerland) · 2026Review
- Multivalent antibody-based conjugates as new tools for tailored modulation of G protein-coupled receptors.British journal of pharmacology · 2026Review
- Bioorthogonal Activation of Protein Function through a retro-Cope/Cope Elimination Cascade.Journal of the American Chemical Society · 2026Article
- Aliphatic Poly(Carbonate)s with Acid Responsive Release Mechanisms for Micellar Anti-Tumor Drug Delivery.Macromolecular rapid communications · 2026Review
- Spontaneous Non-Catalyzed Molecular Reactions and Interactions in the Human Body: Biomedical Implications.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Review
- Smart responsive hydrogels combined with AI design for tumor therapy.Acta pharmaceutica Sinica. B · 2026Review
- Synthesis of Click-Ready Aminooxy-Terminated Poly(ε-caprolactone) Oligomers for Oxime Ligation.Bioconjugate chemistry · 2026Article
- Going full circle: dynamic covalent enzyme immobilisationChemical science · 2026Article
- It's a Gas: Bioconjugation With Vapor-Phase Reagents.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- The Role of Cyclodextrins in Modulating Stimuli-Responsiveness for Anticancer Drug Delivery.Pharmaceutical research · 2026Review
- Scalable Flow Synthesis of Genetically Encodable Tetrazine Amino Acids.Organic process research & development · 2026Article
- Polymer Drug Conjugate: A Revolution in Drug Delivery.AAPS PharmSciTech · 2026Review
- On-Demand Chemically Degradable Hydrogels for Biological Applications.Chembiochem : a European journal of chemical biology · 2026Review
161 more citing papers are in PubMed but not listed here.
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Authors and funding
2 authors.
Funding
Abstract
The formation of oximes and hydrazones is employed in numerous scientific fields as a simple and versatile conjugation strategy. This imine-forming reaction is applied in fields as diverse as polymer chemistry, biomaterials and hydrogels, dynamic combinatorial chemistry, organic synthesis, and chemical biology. Here we outline chemical developments in this field, with special focus on the past ∼10 years of developments. Recent strategies for installing reactive carbonyl groups and α-nucleophiles into biomolecules are described. The basic chemical properties of reactants and products in this reaction are then reviewed, with an eye to understanding the reaction's mechanism and how reactant structure controls rates and equilibria in the process. Recent work that has uncovered structural features and new mechanisms for speeding the reaction, sometimes by orders of magnitude, is discussed. We describe recent studies that have identified especially fast reacting aldehyde/ketone substrates and structural effects that lead to rapid-reacting α-nucleophiles as well. Among the most effective new strategies has been the development of substituents near the reactive aldehyde group that either transfer protons at the transition state or trap the initially formed tetrahedral intermediates. In addition, the recent development of efficient nucleophilic catalysts for the reaction is outlined, improving greatly upon aniline, the classical catalyst for imine formation. A number of uses of such second- and third-generation catalysts in bioconjugation and in cellular applications are highlighted. While formation of hydrazone and oxime has been traditionally regarded as being limited by slow rates, developments in the past 5 years have resulted in completely overturning this limitation; indeed, the reaction is now one of the fastest and most versatile reactions available for conjugations of biomolecules and biomaterials.
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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.