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  • Guanidinoneomycin-maleimide molecular transporter: synthesis, chemistry and cellular uptake.

Guanidinoneomycin-maleimide molecular transporter: synthesis, chemistry and cellular uptake.

Organic & biomolecular chemistry (2021-07-14)
Kaivin Hadidi, Maria Cristina Bellucci, Sergio Dall'Angelo, Alasdair Leeson-Payne, Justin J Rochford, Jeffery D Esko, Yitzhak Tor, Alessandro Volonterio
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.

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