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.

Guanidinoneomycin-maleimide molecular transporter: synthesis, chemistry and cellular uptake / K. Hadidi, M.C. Bellucci, S. Dall'Angelo, A. Leeson-Payne, J.J. Rochford, J.D. Esko, Y. Tor, A. Volonterio. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - 19:29(2021), pp. 6513-6520. [10.1039/d1ob01101d]

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

M.C. Bellucci
Secondo
;
S. Dall'Angelo;
2021

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.
Maleimides
Settore CHIM/06 - Chimica Organica
Article (author)
File in questo prodotto:
File Dimensione Formato  
OBC_2021.pdf

accesso aperto

Tipologia: Publisher's version/PDF
Dimensione 1.51 MB
Formato Adobe PDF
1.51 MB Adobe PDF Visualizza/Apri
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/929926
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 0
  • ???jsp.display-item.citation.isi??? 0
social impact