ArticleACS medicinal chemistry letters2016
Site-Specific Tandem Knoevenagel Condensation-Michael Addition To Generate Antibody-Drug Conjugates.
Article in ACS medicinal chemistry letters, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Self-reporting photodynamic nanobody conjugate for precise and sustainable large-volume tumor treatment.Nature communications · 2024Article
- Introduction of Carbonyl Groups into Antibodies.Molecules (Basel, Switzerland) · 2023Review
- Review
- Galactose Oxidase Enables Modular Assembly of Conjugates from Native Antibodies with High Drug-to-Antibody Ratios.ChemSusChem · 2022Article
- Bivalent EGFR-Targeting DARPin-MMAE Conjugates.International journal of molecular sciences · 2022Article
- A Not-So-Ancient Grease History: Click Chemistry and Protein Lipid Modifications.Chemical reviews · 2021Review
- Toward Homogenous Antibody Drug Conjugates Using Enzyme-Based Conjugation Approaches.Pharmaceuticals (Basel, Switzerland) · 2021Review
- Bifunctional Reagents for Formylglycine Conjugation: Pitfalls and Breakthroughs.Chembiochem : a European journal of chemical biology · 2020Article
- Pyrazolone ligation-mediated versatile sequential bioconjugations.Chemical science · 2020Article
- Click Chemistry Conjugations.Methods in molecular biology (Clifton, N.J.) · 2020Article
- A Case Study to Identify the Drug Conjugation Site of a Site-Specific Antibody-Drug-Conjugate Using Middle-Down Mass Spectrometry.Journal of the American Society for Mass Spectrometry · 2019Article
- Site-Specific Bioconjugation and Multi-Bioorthogonal Labeling via Rapid Formation of a Boron-Nitrogen Heterocycle.Bioconjugate chemistry · 2019Article
- Recent progress in enzymatic protein labelling techniques and their applications.Chemical Society reviews · 2018Review
- Efficient promiscuous Knoevenagel condensation catalyzed by papain confined in CuRSC advances · 2018Article
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9 authors.
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Abstract
Expanded ligation techniques are sorely needed to generate unique linkages for the growing field of functionally enhanced proteins. To address this need, we present a unique chemical ligation that involves the double addition of a pyrazolone moiety with an aldehyde-labeled protein. This ligation occurs via a tandem Knoevenagel condensation-Michael addition. A pyrazolone reacts with an aldehyde to generate an enone, which undergoes subsequent attack by a second pyrazolone to generate a bis-pyrazolone species. This rapid and facile ligation technique is performed under mild conditions in the absence of catalyst to generate new architectures that were previously inaccessible via conventional ligation reactions. Using this unique ligation, we generated three site-specifically labeled antibody-drug conjugates (ADCs) with an average of four drugs to one antibody. The in vitro and in vivo efficacies along with pharmacokinetic data of the site-specific ADCs are reported.
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