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Synthesis of novel bis-triazolinedione crosslinked amphiphilic polypept(o)ide nanostructures

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journal contribution
posted on 26.04.2021, 16:36 authored by Ruairi Brannigan, Scott D Kimmins, Elena Bobbi, Séamus Caulfield, Andreas HeiseAndreas Heise
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.


European Union’s Horizon 2020 research and innovation programme under the Marie Skłodowska– Curie grant agreement No 748364 (EsterPep)

Translational Research in Nanomedical Devices (TREND) project

Science Foundation Ireland Investigators Program (Grant code 13/ IA/1840)



This is the peer reviewed version of the following article: Brannigan RP, Kimmins SD, Bobbi E, Caufield S. Heise A. Synthesis of Novel bis-Triazolinedione Crosslinked Amphiphilic Polypept(o)ide Nanostructures. Macromolecular Chemistry and Physics. 2019;220(11):1900067, which has been published in final form at https://doi.org/10.1002/macp.201900067. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.

Published Citation

Brannigan RP, Kimmins SD, Bobbi E, Caufield S. Heise A. Synthesis of novel bis-triazolinedione crosslinked amphiphilic polypept(o)ide nanostructures. Macromolecular Chemistry and Physics. 2019;220(11):1900067.

Publication Date

25 April 2019


  • Chemistry

Research Area

  • Chemistry and Pharmaceutical Sciences
  • Biomaterials and Regenerative Medicine




  • Accepted Version (Postprint)