Tetrazine- and trans -cyclooctene-functionalised polypept(o)ides for fast bioorthogonal tetrazine ligation
| Autor: | Lydia Braun, Kaloian Koynov, Silvia Rizzelli, Hannes Mikula, Christine Seidl, Matthias Barz, Tobias Bauer, Kerstin Johann, Dennis Svatunek |
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| Rok vydání: | 2020 |
| Předmět: |
Polymers and Plastics
Chemistry Organic Chemistry Bioengineering 02 engineering and technology 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Gel permeation chromatography Miniemulsion End-group chemistry.chemical_compound Tetrazine Cyclooctene Click chemistry Reactivity (chemistry) Bioorthogonal chemistry 0210 nano-technology |
| Zdroj: | Polymer Chemistry Polymer Chemistry, 11(27), 4396-4407. ROYAL SOC CHEMISTRY |
| ISSN: | 1759-9954 |
| DOI: | 10.1039/d0py00375a |
| Popis: | The inverse electron demand Diets-Alder (IEDDA) reaction-initiated ligation between 1,2,4,5-tetra-zines (Tz) and trans-cyclooctenes (TCO) is one of the fastest bioorthogonal reactions known today and is therefore increasingly used for in vivo click chemistry. Described herein is the synthesis of Tz- and TCO-functionalised polypeptides, polypeptoids and polypeptide-block-polypeptoids (polypept(o) ides) by ring-opening polymerisation of the corresponding N-carboxyanhydrides using Tz- or TCO-functional amine initiators. Despite the reactivity of tetrazines, polymers with low dispersity and high end group integrity can be obtained as observed by gel permeation chromatography (GPC), nuclear magnetic resonance (NMR) spectroscopy and matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry. Amphiphilic Tz-functionalised block copolypept(o)ides were used to prepare polymeric micelles and organic colloids by miniemulsion techniques, which may find an application as clearing agents in pretargeted nuclear imaging and therapy using efficient in vivo click chemistry. The reaction kinetics of the tetrazine ligation using the synthesised polymers and the accessibility of the Tz groups on the polymeric nanoparticles were evaluated using UV Vis and fluorescence correlation spectroscopy (FCS), and second-order rate constants were determined by stopped-flow spectrophotometry ensuring quantitative conversions in seconds at sub-millimolar concentrations (10-30 s). |
| Databáze: | OpenAIRE |
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