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

2 Citations (Scopus)
3 Downloads (Pure)


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
Pages (from-to)6513-6520
Number of pages8
JournalOrganic & Biomolecular Chemistry
Issue number29
Early online date6 Jul 2021
Publication statusE-pub ahead of print - 6 Jul 2021

Bibliographical note

We thank the Fulbright Program for a Research Scholar Fellowship (A.V.) and the National Science Foundation for support (via grant number CHE-1303554), the Biotechnology and Biological Sciences Research Council [BB/K017772/1] (J.J.R.) as well as the Chemistry and Biochemistry MS and NMR Facilities.


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