ArticleBioconjugate chemistry2012
Application of strain-promoted azide-alkyne cycloaddition and tetrazine ligation to targeted Fc-drug conjugates.
Article in Bioconjugate chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Development of Essential Oil Delivery Systems by 'Click Chemistry' Methods: Possible Ways to Manage Duchenne Muscular Dystrophy.Materials (Basel, Switzerland) · 2023Review
- Functionalized Triazines and Tetrazines: Synthesis and Applications.Topics in current chemistry (Cham) · 2022Review
- Stable and Potent Selenomab-Drug Conjugates.Cell chemical biology · 2017Article
- An Umpolung Approach for the Chemoselective Arylation of Selenocysteine in Unprotected Peptides.Journal of the American Chemical Society · 2015Article
- An evolved Mxe GyrA intein for enhanced production of fusion proteins.ACS chemical biology · 2015Article
- Chemically programmed antibodies.Trends in biotechnology · 2014Review
- A general method for artificial metalloenzyme formation through strain-promoted azide-alkyne cycloaddition.Chembiochem : a European journal of chemical biology · 2014Article
- Antibody conjugation via one and two C-terminal selenocysteines.Methods (San Diego, Calif.) · 2014Article
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
We have previously described an approach whereby antibody Fc fragments harboring a single C-terminal selenocysteine residue (Fc-Sec) are directed against a variety of targets by changing the peptide or small molecule to which they are conjugated. In the present work, we describe methodology for improving the efficacy of these Fc-Sec conjugates by incorporating cytotoxic drugs. The Fc-Sec protein is first programmed to target specific tumor cell types by attachment of a bifunctional linker that contains a "clickable" handle (e.g., cyclobutane or cyclooctyne) in addition to a tumor cell-binding peptide or small molecule. Following Fc-Sec conjugation, a cytotoxic warhead is then attached by cycloaddition reactions of tetrazine or azide-containing linker. To validate this approach, we used a model system in which folic acid (FA) is the targeting moiety and a disulfide-linked biotin moiety serves as a cytotoxic drug surrogate. We demonstrated successful targeting of Fc-Sec proteins to folate-receptor expressing tumor cells. Tetrazine ligation was found to be an efficient method for biotin "arming" of the folate-targeted Fc-Sec proteins. We also report novel bioconjugation methodologies that use [4 + 2] cycloaddition reactions between tetrazines and cyclooctynes.
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Registered trials
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