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Water-Compatible Staudinger-Diels-Alder Ligation.
J Org Chem
January 2025
Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
The development of bioorthogonal reactions is expected to propel further advances in chemical biology. In this study, we demonstrate Staudinger-Diels-Alder (SDA) ligation as a candidate for a new bioorthogonal reaction. This reaction ligates two molecules via strong C-C bonds at room temperature.
View Article and Find Full Text PDFInnovative Peptide Bioconjugation Chemistry with Radionuclides: Beyond Classical Click Chemistry.
Pharmaceuticals (Basel)
September 2024
Department of Oncology, Faculty of Medicine and Dentistry, University of Alberta, Edmonton, AB T6G 1Z2, Canada.
: The incorporation of radionuclides into peptides and larger biomolecules requires efficient and sometimes biorthogonal reaction conditions, to which click chemistry provides a convenient approach. : Traditionally, click-based radiolabeling techniques have focused on classical click chemistry, such as copper(I)-catalyzed alkyne-azide [3+2] cycloaddition (CuAAC), strain-promoted azide-alkyne [3+2] cycloaddition (SPAAC), traceless Staudinger ligation, and inverse electron demand Diels-Alder (IEDDA). : However, newly emerging click-based radiolabeling techniques, including tyrosine-click, sulfo-click, sulfur(VI) fluoride exchange (SuFEx), thiol-ene click, azo coupling, hydrazone formations, oxime formations, and RIKEN click offer valuable alternatives to classical click chemistry.
View Article and Find Full Text PDFClick Chemistry Enables [Zr]Zr-DOTA Radioimmunoconjugation for Theranostic Zr-immunoPET.
Bioconjug Chem
November 2024
Isotope Science Center, The University of Tokyo, Bunkyo, Tokyo 113-0032, Japan.
There have been predictions that the use of the macrocyclic chelating agent 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) in zirconium-89 (Zr) immuno-positron emission tomography (Zr-immunoPET) could enhance the in vivo stability of Zr radioimmunoconjugates. However, conjugating [Zr]Zr-DOTA to a monoclonal antibody (mAb) remains a challenge as the heat treatment required for [Zr]Zr-DOTA chelation can lead to thermal denaturation of the mAb moieties. We developed a method for synthesizing [Zr]Zr-DOTA-mAb based on a tetrazine (Tz)-conjugated bifunctional DOTA derivative 2,2',2″-(10-(1-(4-(1,2,4,5-tetrazin-3-yl)phenyl)-3,21,26-trioxo-6,9,12,15,18-pentaoxa-29-carboxy-2,22,25-triazanonacosane-29-yl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid (DOTAGA-Tz) and the inverse electron-demand Diels-Alder (IEDDA) click chemistry reaction where -cyclooctene-modified mAbs are conjugated to [Zr]Zr-DOTAGA without being exposed to heat.
View Article and Find Full Text PDFTetrazine-trans-cyclooctene ligation: Unveiling the chemistry and applications within the human body.
Bioorg Chem
September 2024
Department of Drug and Health Sciences, University of Catania, V.le A. Doria 6, 95125 Catania, Italy.
Bioorthogonal reactions have revolutionized chemical biology by enabling selective chemical transformations within living organisms and cells. This review comprehensively explores bioorthogonal chemistry, emphasizing inverse-electron-demand Diels-Alder (IEDDA) reactions between tetrazines and strained dienophiles and their crucial role in chemical biology and various applications within the human body. This highly reactive and selective reaction finds diverse applications, including cleaving antibody-drug conjugates, prodrugs, proteins, peptide antigens, and enzyme substrates.
View Article and Find Full Text PDFTrans-cyclooctene-a Swiss army knife for bioorthogonal chemistry: exploring the synthesis, reactivity, and applications in biomedical breakthroughs.
EJNMMI Radiopharm Chem
June 2024
Molecular Imaging and Radiology, University of Antwerp, Antwerp, Belgium.
Background: Trans-cyclooctenes (TCOs) are highly strained alkenes with remarkable reactivity towards tetrazines (Tzs) in inverse electron-demand Diels-Alder reactions. Since their discovery as bioorthogonal reaction partners, novel TCO derivatives have been developed to improve their reactivity, stability, and hydrophilicity, thus expanding their utility in diverse applications.
Main Body: TCOs have garnered significant interest for their applications in biomedical settings.
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