Synthesis of Novel bis-Triazolinedione Crosslinked Amphiphilic Polypept(o)ide Nanostructures

Ruairí P. Brannigan, Scott D. Kimmins, Elena Bobbi, Séamus Caulfield, Andreas Heise

Research output: Contribution to journalArticlepeer-review

6 Scopus citations


Owing to their wide range of inherent functionality, hydrolytic stability, biodegradability, and low toxicity, polypeptide-based materials have been increasingly exploited for controlled drug release applications. More recently, the incorporation of poly(α-peptoid)s such as poly(sarcosine) into polypeptide-based materials has been investigated owing to their potential as naturally derived “stealth polymers.” Here the synthesis of novel amphiphilic polypept(o)ide nanoparticles is described utilizing silica templates as a macroinitiator for the ring-opening copolymerization of l-tryptophan and d/l-phenylalanine NCAs and subsequent chain extension with sarcosine NCA. These particles are subsequently crosslinked utilizing the TAD-indole “click” chemistry and the silica templates are eroded via treatment with HF yielding core crosslinked amphiphilic polypept(o)ide nanostructures. This synthetic strategy offers a unique platform to yield naturally-derived degradable core-crosslinked nanostructures, which may have the potential to be utilized in the future as delivery vehicles for hydrophobic small molecules.

Original languageEnglish
Article number1900067
JournalMacromolecular Chemistry and Physics
Issue number11
StatePublished - Jun 2019
Externally publishedYes


  • amphiphiles
  • crosslinking
  • nanoparticles
  • peptides
  • ring-opening polymerization


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