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Synthesis of Novel bis ‐Triazolinedione Crosslinked Amphiphilic Polypept(o)ide Nanostructures
Author(s) -
Brannigan Ruairí P.,
Kimmins Scott D.,
Bobbi Elena,
Caulfield Séamus,
Heise Andreas
Publication year - 2019
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201900067
Subject(s) - amphiphile , sarcosine , copolymer , chemistry , polymer chemistry , polymer , template , micelle , nanoparticle , click chemistry , peptoid , drug delivery , combinatorial chemistry , materials science , nanotechnology , organic chemistry , peptide , aqueous solution , amino acid , glycine , biochemistry
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.