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"Clicking" trimeric peptides onto hybrid T 8 POSS nanocages and identifying synthesis limitations.

Lewis R AndersonAnn P HunterMatthew J KershawSergey Y BylikinJames BowenPeter G TaylorMartin A BirchallNazia Mehrban
Published in: Nanoscale (2024)
Macromolecule branching upon polyhedral oligomeric silsesquioxanes (POSS) via "click" chemistry has previously been reported for promoting natural biological responses in vitro , particularly when regarding their demonstrated biocompatibility and structural robustness as potential macromolecule anchoring points. However, "clicking" of large molecules around POSS structures uncovers two main challenges: (1) a synthetic challenge encompassing multi-covalent attachment of macromolecules to a single nanoscale-central position, and (2) purification and separation of fully adorned nanocages from those that are incomplete due to their similar physical characteristics. Here we present peptide decoration to a T 8 POSS nanocage through the attachment of azido-modified trimers. Triglycine- and trialanine-methyl esters "clicked" to 97% and 92% completion, respectively, resulting in 84% and 68% yields of the fully-adorned octamers. The "clicks" halt within 27-h of the reaction time, and efforts to further increase the octamer yield were of negligible benefit. Exploration of reaction conditions reveals multiple factors preventing full octa-arm modification to all available POSS nanocages, and offers insights into macromolecule attachment between both peptides and small inorganic-organic structures, all of which require consideration for future work of this nature.
Keyphrases
  • high resolution
  • physical activity
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  • liquid chromatography
  • mass spectrometry
  • atomic force microscopy
  • water soluble
  • tissue engineering