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Name Mr. Alban H. R. Charlier
Organization or Institution University of Florida
Presentation Type Poster
Topic Physical Chemistry
Title

Developing polypeptide-based drug delivery vehicles for improved cancer therapeutics

Author(s)

Alban H. R. Charlier, Ian R. Smith, Daniel A. Savin

Author Institution(s)

Department of Chemistry, University of Florida, Gainesville FL 32611-7200, USA

Abstract

Herein, we describe the facile synthesis of a peptide amphiphile (PA) derived from N- carboxy
anhydrides (NCA), and subsequent aqueous solution characterization of the self- assembled
nanostructures. Peptide amphiphiles are saturated hydrocarbon chains covalently attached to a short
polypeptide chain. The polymerization of N-carboxy anhydrides is a common technique employed for the
synthesis of polypeptides. Cyanuric chloride, or 2,4,6-trichloro-1,3,5- triazine (TCT), was employed as a
modular platform to synthesize the lipid-mimetic macroinitiator, to which was installed a nitroxide radical
for electron paramagnetic resonance (EPR) spectroscopy and a primary amine for the ring opening
polymerization of γ-t-butyl-L-glutamic acid NCA. After deprotection of the polypeptide, we studied the selfassembly
behavior of pH- responsive polyglutamate-b-octadecanethiol2 via static and dynamic light
scattering, then utilized EPR to probe the local characteristics at the surface of the membrane of the
nanostructure. This simple and modular synthetic approach allows for the design of PAs with tailor-made
chemical and physical properties, and the self-assembled nanostructures have a direct application as a drug
delivery vehicle for cancer therapeutics.