Design of pH-Degradable Polymer-Lipid Amphiphiles Using a Ketal-Functionalized RAFT Chain Transfer Agent.

Macromolecular Rapid Communications
Jana De VriezeBruno G De Geest

Abstract

Conjugation of small molecule drug to lipid-polymer amphiphiles is a powerful strategy to alter the pharmacokinetic profile of these molecules by promoting binding to albumin or other serum molecules. Incorporation of a responsive linker between the lipid anchor and the polymer chain can be of interest to avoid indefinite binding of the conjugates to hydrophobic pockets of serum proteins or phospholipid membranes when reaching a target cell or tissue. Here, the synthesis of pH-sensitive lipid-polymer conjugates by reversible addition-fragmentation chain transfer (RAFT) polymerization using a RAFT chain transfer agent that is equipped with a pH-sensitive ketal bond between a cholesterol moiety and the trithiocarbonate RAFT chain transfer group is reported. It is demonstrated that in native form these conjugates exhibit a high affinity to albumin and cell membranes but loose this ability in response to a mild acidic trigger in aqueous medium.

References

Sep 18, 2007·Nature Biotechnology·Christian WolfrumMarkus Stoffel
Sep 22, 2009·Chemical Reviews·Cyrille BoyerSébastien Perrier
Jan 16, 2013·Chemical Communications : Chem Comm·Sandra Binauld, Martina H Stenzel
Mar 26, 2013·International Journal of Pharmaceutics·Iljae LeeDongwon Lee
Feb 18, 2014·Nature·Haipeng LiuDarrell J Irvine
Jun 7, 2014·Journal of the American Chemical Society·Yao-Rong ZhengStephen J Lippard
Nov 21, 2014·Science Translational Medicine·Tom Y-H WuNicholas M Valiante
Oct 9, 2015·Translational Neurodegeneration·Yong-Bo HuGang Wang
Dec 10, 2015·Angewandte Chemie·Elliot C WoodsCarolyn R Bertozzi
Jul 7, 2016·Proceedings of the National Academy of Sciences of the United States of America·Lutz NuhnBruno G De Geest

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