Synthesis of Amphiphilic Block Copolypept(o)ides by Bifunctional Initiators: Making PeptoMicelles Redox Sensitive

Macromolecular Rapid Communications
Regina HolmM Barz

Abstract

In this work, the synthesis of polypeptoid-block-polypeptide copolymers (block copolypept(o)ides) based on bifunctional initiators is described, which introduces a distinct chemical entity at the connection between both blocks. With a view towards redox-sensitive block copolypept(o)ides, a cystamine-based initiator was used to synthesize polysarcosine macroinitiators with degrees of polymerization (Xn) between 100 and 200 displaying monomodal molecular weight distributions and dispersities (Đ) around 1.1 as determined by size exclusion chromatography. Block copolypept(o)ides with a poly(γ-t-butyloxycarbonyl-L-glutamate) (PGlu(O(t) Bu)) block (Xn = 25 or 50) were synthesized by controlled N-carboxyanhydride polymerization. Resulting block copolymers possess monomodal molecular weight distributions, dispersities around 1.2 and were applied to degradation studies. While block copolypept(o)ides are stable at 10 × 10(-6) M, they degrade over time at GSH concentrations of 10 × 10(-3) and 100 × 10(-3) M. Furthermore, these disulfide-containing block copolymers form PeptoMicelles, which degrade at intracellular GSH concentrations while remaining stable at extracellular GSH levels.

References

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Oct 14, 2003·Biochemical Pharmacology·Alfonso PompellaAlessandro F Casini
Feb 1, 2012·Macromolecular Rapid Communications·Gijs J M HabrakenPaul D Thornton
Nov 28, 2012·Advanced Healthcare Materials·Chaoliang HeXuesi Chen
Nov 20, 2013·Redox Biology·Davide MonteroChristian Appenzeller-Herzog
Jul 6, 2014·Journal of Controlled Release : Official Journal of the Controlled Release Society·Horacio Cabral, Kazunori Kataoka
Nov 2, 2014·Macromolecular Rapid Communications·Philipp HellerMatthias Barz

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Citations

Dec 25, 2015·Chemical Reviews·Niklas GangloffRobert Luxenhofer
Sep 24, 2015·Macromolecular Rapid Communications·Kristina Klinker, Matthias Barz
Oct 27, 2017·Biopolymers·Brandon A ChanDonghui Zhang
Feb 13, 2018·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Bradford A PaikKristi L Kiick
Aug 11, 2021·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Tobias Alexander BauerMatthias Barz

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