Synthesis and mechanistic investigations of pH-responsive cationic poly(aminoester)s
Abstract
The synthesis and degradation mechanisms of a class of pH-sensitive, rapidly degrading cationic poly(α-aminoester)s are described. These reactive, cationic polymers are stable at low pH in water, but undergo a fast and selective degradation at higher pH to liberate neutral diketopiperazines. Related materials incorporating oligo(α-amino ester)s have been shown to be effective gene delivery agents, as the charge-altering degradative behavior facilitates the delivery and release of mRNA and other nucleic acids in vitro and in vivo. Herein, we report detailed studies of the structural and environmental factors that lead to these rapid and selective degradation processes in aqueous buffers. At neutral pH, poly(α-aminoester)s derived from N-hydroxyethylglycine degrade selectively by a mechanism involving sequential 1,5- and 1,6-O→N acyl shifts to generate bis(N-hydroxyethyl) diketopiperazine. A family of structurally related cationic poly(aminoester)s was generated to study the structural influences on the degradation mechanism, product distribution, and pH dependence of the rate of degradation. The kinetics and mechanism of the pH-induced degradations were investigated by 1H NMR, model reactions, and kinetic simulations. These results indicate that polyesters bearing α-ammonium groups and appropriately positioned N-hydroxyethyl substituents are readily cleaved (by intramolecular attack) or hydrolyzed, representing dynamic “dual function” materials that are initially polycationic and transformmore »
- Authors:
-
[1];
[1];
[1]
- Department of Chemistry, Stanford University, Stanford, USA
- Department of Chemistry, Stanford University, Stanford, USA, Department of Chemical and Systems Biology
- Publication Date:
- Research Org.:
- Stanford Univ., CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1600850
- Alternate Identifier(s):
- OSTI ID: 1803272
- Grant/Contract Number:
- SC0018168
- Resource Type:
- Published Article
- Journal Name:
- Chemical Science
- Additional Journal Information:
- Journal Name: Chemical Science Journal Volume: 11 Journal Issue: 11; Journal ID: ISSN 2041-6520
- Publisher:
- Royal Society of Chemistry (RSC)
- Country of Publication:
- United Kingdom
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Blake, Timothy R., Ho, Wilson C., Turlington, Christopher R., Zang, Xiaoyu, Huttner, Melanie A., Wender, Paul A., and Waymouth, Robert M. Synthesis and mechanistic investigations of pH-responsive cationic poly(aminoester)s. United Kingdom: N. p., 2020.
Web. doi:10.1039/C9SC05267D.
Blake, Timothy R., Ho, Wilson C., Turlington, Christopher R., Zang, Xiaoyu, Huttner, Melanie A., Wender, Paul A., & Waymouth, Robert M. Synthesis and mechanistic investigations of pH-responsive cationic poly(aminoester)s. United Kingdom. https://doi.org/10.1039/C9SC05267D
Blake, Timothy R., Ho, Wilson C., Turlington, Christopher R., Zang, Xiaoyu, Huttner, Melanie A., Wender, Paul A., and Waymouth, Robert M. Wed .
"Synthesis and mechanistic investigations of pH-responsive cationic poly(aminoester)s". United Kingdom. https://doi.org/10.1039/C9SC05267D.
@article{osti_1600850,
title = {Synthesis and mechanistic investigations of pH-responsive cationic poly(aminoester)s},
author = {Blake, Timothy R. and Ho, Wilson C. and Turlington, Christopher R. and Zang, Xiaoyu and Huttner, Melanie A. and Wender, Paul A. and Waymouth, Robert M.},
abstractNote = {The synthesis and degradation mechanisms of a class of pH-sensitive, rapidly degrading cationic poly(α-aminoester)s are described. These reactive, cationic polymers are stable at low pH in water, but undergo a fast and selective degradation at higher pH to liberate neutral diketopiperazines. Related materials incorporating oligo(α-amino ester)s have been shown to be effective gene delivery agents, as the charge-altering degradative behavior facilitates the delivery and release of mRNA and other nucleic acids in vitro and in vivo. Herein, we report detailed studies of the structural and environmental factors that lead to these rapid and selective degradation processes in aqueous buffers. At neutral pH, poly(α-aminoester)s derived from N-hydroxyethylglycine degrade selectively by a mechanism involving sequential 1,5- and 1,6-O→N acyl shifts to generate bis(N-hydroxyethyl) diketopiperazine. A family of structurally related cationic poly(aminoester)s was generated to study the structural influences on the degradation mechanism, product distribution, and pH dependence of the rate of degradation. The kinetics and mechanism of the pH-induced degradations were investigated by 1H NMR, model reactions, and kinetic simulations. These results indicate that polyesters bearing α-ammonium groups and appropriately positioned N-hydroxyethyl substituents are readily cleaved (by intramolecular attack) or hydrolyzed, representing dynamic “dual function” materials that are initially polycationic and transform with changing environment to neutral products.},
doi = {10.1039/C9SC05267D},
journal = {Chemical Science},
number = 11,
volume = 11,
place = {United Kingdom},
year = {2020},
month = {3}
}
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