Guanidinoneomycin-Maleimide Molecular Transporter: Synthesis, Chemistry and Cellular Uptake

Kaivin Hadidi, Maria Cristina Bellucci, Sergio Dall'Angelo, Alasdair Leeson-Payne, Justin J Rochford, Jeffery D. Esko, Yitzhak Tor* (Corresponding Author), Alessandro Volonterio

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

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.
Original languageEnglish
JournalOrganic & Biomolecular Chemistry
Issue number29
Early online date6 Jul 2021
DOIs
Publication statusE-pub ahead of print - 6 Jul 2021

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