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Polypeptides with Quaternary Phosphonium Side Chains: Synthesis, Characterization, and Cell-Penetrating Properties
[Image: see text] Polypeptides bearing quaternary phosphonium side chains were synthesized via controlled ring-opening polymerization of chlorine-functionalized amino acid N-carboxyanhydride monomers followed by one-step nucleophilic substitution reaction with triethylphosphine. The conformation of...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American
Chemical Society
2014
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3993874/ https://www.ncbi.nlm.nih.gov/pubmed/24635536 http://dx.doi.org/10.1021/bm5001026 |
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author | Song, Ziyuan Zheng, Nan Ba, Xiaochu Yin, Lichen Zhang, Rujing Ma, Liang Cheng, Jianjun |
author_facet | Song, Ziyuan Zheng, Nan Ba, Xiaochu Yin, Lichen Zhang, Rujing Ma, Liang Cheng, Jianjun |
author_sort | Song, Ziyuan |
collection | PubMed |
description | [Image: see text] Polypeptides bearing quaternary phosphonium side chains were synthesized via controlled ring-opening polymerization of chlorine-functionalized amino acid N-carboxyanhydride monomers followed by one-step nucleophilic substitution reaction with triethylphosphine. The conformation of the resulting polypeptides can be controlled by modulating the side-chain length and α-carbon stereochemistry. The phosphonium-based poly(l-glutamate) derivatives with 11 σ-bond backbone-to-charge distance adopt stable α-helical conformation against pH and ionic strength changes. These helical, quaternary phosphonium-bearing polypeptides exhibit higher cell-penetrating capability than their racemic and random-coiled analogues. They enter cells mainly via an energy-independent, nonendocytic cell membrane transduction mechanism and exhibit low cytotoxicity, substantiating their potential use as a safe and effective cell-penetrating agent. |
format | Online Article Text |
id | pubmed-3993874 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | American
Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-39938742015-03-06 Polypeptides with Quaternary Phosphonium Side Chains: Synthesis, Characterization, and Cell-Penetrating Properties Song, Ziyuan Zheng, Nan Ba, Xiaochu Yin, Lichen Zhang, Rujing Ma, Liang Cheng, Jianjun Biomacromolecules [Image: see text] Polypeptides bearing quaternary phosphonium side chains were synthesized via controlled ring-opening polymerization of chlorine-functionalized amino acid N-carboxyanhydride monomers followed by one-step nucleophilic substitution reaction with triethylphosphine. The conformation of the resulting polypeptides can be controlled by modulating the side-chain length and α-carbon stereochemistry. The phosphonium-based poly(l-glutamate) derivatives with 11 σ-bond backbone-to-charge distance adopt stable α-helical conformation against pH and ionic strength changes. These helical, quaternary phosphonium-bearing polypeptides exhibit higher cell-penetrating capability than their racemic and random-coiled analogues. They enter cells mainly via an energy-independent, nonendocytic cell membrane transduction mechanism and exhibit low cytotoxicity, substantiating their potential use as a safe and effective cell-penetrating agent. American Chemical Society 2014-03-06 2014-04-14 /pmc/articles/PMC3993874/ /pubmed/24635536 http://dx.doi.org/10.1021/bm5001026 Text en Copyright © 2014 American Chemical Society |
spellingShingle | Song, Ziyuan Zheng, Nan Ba, Xiaochu Yin, Lichen Zhang, Rujing Ma, Liang Cheng, Jianjun Polypeptides with Quaternary Phosphonium Side Chains: Synthesis, Characterization, and Cell-Penetrating Properties |
title | Polypeptides with Quaternary Phosphonium Side Chains:
Synthesis, Characterization, and Cell-Penetrating Properties |
title_full | Polypeptides with Quaternary Phosphonium Side Chains:
Synthesis, Characterization, and Cell-Penetrating Properties |
title_fullStr | Polypeptides with Quaternary Phosphonium Side Chains:
Synthesis, Characterization, and Cell-Penetrating Properties |
title_full_unstemmed | Polypeptides with Quaternary Phosphonium Side Chains:
Synthesis, Characterization, and Cell-Penetrating Properties |
title_short | Polypeptides with Quaternary Phosphonium Side Chains:
Synthesis, Characterization, and Cell-Penetrating Properties |
title_sort | polypeptides with quaternary phosphonium side chains:
synthesis, characterization, and cell-penetrating properties |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3993874/ https://www.ncbi.nlm.nih.gov/pubmed/24635536 http://dx.doi.org/10.1021/bm5001026 |
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