Guanidinoneomycin-maleimide molecular transporter: synthesis, chemistry and cellular uptake
| Autor: | Sergio Dall'Angelo, Maria Cristina Bellucci, Alessandro Volonterio, Alasdair Leeson-Payne, Justin J. Rochford, Yitzhak Tor, Jeffery D Esko, Kaivin Hadidi |
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| Rok vydání: | 2021 |
| Předmět: |
aminoglycosides
Bioconjugation 010405 organic chemistry Organic Chemistry guanidinoneomycin Settore CHIM/06 - Chimica Organica 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Chemical synthesis 0104 chemical sciences Maleimides chemistry.chemical_compound chemistry molecular transponder drug delivery Drug delivery Click chemistry Moiety Physical and Theoretical Chemistry Linker Maleimide Derivative (chemistry) |
| Zdroj: | Organic & Biomolecular Chemistry. 19:6513-6520 |
| ISSN: | 1477-0539 1477-0520 |
| Popis: | Guanidinoglycosides are a class of non-cytotoxic molecular transporters capable of delivering high molecular weight bioactive cargos into cells at low nanomolar concentrations. Efficient bioconjugation with guanidinoglycosides has been previously demonstrated by utilizing a guanidinoneomycin decorated with a reactive but also unstable N-hydroxysuccinimmide ester-containing linker. Herein we report the synthesis, chemistry, and application of a new, stable guanidinoneomycin derivative armed with a highly specific maleimide moiety which allows for thiol-maleimide click chemistry, a highly popular bioconjugation strategy, widening the field of application of these intriguing and useful delivery vehicles. |
| Databáze: | OpenAIRE |
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