Guanidinoneomycin-maleimide molecular transporter: synthesis, chemistry and cellular uptake. Issue 29 (13th July 2021)

• Record Type: Journal Article
• Authors: Hadidi, Kaivin; Bellucci, Maria Cristina; Dall'Angelo, Sergio; Leeson-Payne, Alasdair; Rochford, Justin J.; Esko, Jeffery D.; Tor, Yitzhak; Volonterio, Alessandro
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 29(2021)
• Page Start: 6513
• Page End: 6520
• Publication Date: 2021-07-13
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01101d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Guanidinoneomycin-maleimide is a stable, easy to handle molecular transporter which allows for thiol-maleimide bioconjugation and promotes cellular uptake of high molecular weight cargos at low nanomolar concentrations. 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.