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Cell‐Penetrating Dynamic‐Covalent Benzopolysulfane Networks
Cyclic oligochalcogenides (COCs) are emerging as promising systems to penetrate cells. Clearly better than and different to the reported diselenolanes and epidithiodiketopiperazines, we introduce the benzopolysulfanes (BPS), which show efficient delivery, insensitivity to inhibitors of endocytosis,...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6618005/ https://www.ncbi.nlm.nih.gov/pubmed/31168906 http://dx.doi.org/10.1002/anie.201905003 |
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author | Cheng, Yangyang Zong, Lili López‐Andarias, Javier Bartolami, Eline Okamoto, Yasunori Ward, Thomas R. Sakai, Naomi Matile, Stefan |
author_facet | Cheng, Yangyang Zong, Lili López‐Andarias, Javier Bartolami, Eline Okamoto, Yasunori Ward, Thomas R. Sakai, Naomi Matile, Stefan |
author_sort | Cheng, Yangyang |
collection | PubMed |
description | Cyclic oligochalcogenides (COCs) are emerging as promising systems to penetrate cells. Clearly better than and different to the reported diselenolanes and epidithiodiketopiperazines, we introduce the benzopolysulfanes (BPS), which show efficient delivery, insensitivity to inhibitors of endocytosis, and compatibility with substrates as large as proteins. This high activity coincides with high reactivity, selectively toward thiols, exceeding exchange rates of disulfides under tension. The result is a dynamic‐covalent network of extreme sulfur species, including cyclic oligomers, from dimers to heptamers, with up to nineteen sulfurs in the ring. Selection from this unfolding adaptive network then yields the reactivities and selectivities needed to access new uptake pathways. Contrary to other COCs, BPS show high retention on thiol affinity columns. The identification of new modes of cell penetration is important because they promise new solutions to challenges in delivery and beyond. |
format | Online Article Text |
id | pubmed-6618005 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-66180052019-07-22 Cell‐Penetrating Dynamic‐Covalent Benzopolysulfane Networks Cheng, Yangyang Zong, Lili López‐Andarias, Javier Bartolami, Eline Okamoto, Yasunori Ward, Thomas R. Sakai, Naomi Matile, Stefan Angew Chem Int Ed Engl Communications Cyclic oligochalcogenides (COCs) are emerging as promising systems to penetrate cells. Clearly better than and different to the reported diselenolanes and epidithiodiketopiperazines, we introduce the benzopolysulfanes (BPS), which show efficient delivery, insensitivity to inhibitors of endocytosis, and compatibility with substrates as large as proteins. This high activity coincides with high reactivity, selectively toward thiols, exceeding exchange rates of disulfides under tension. The result is a dynamic‐covalent network of extreme sulfur species, including cyclic oligomers, from dimers to heptamers, with up to nineteen sulfurs in the ring. Selection from this unfolding adaptive network then yields the reactivities and selectivities needed to access new uptake pathways. Contrary to other COCs, BPS show high retention on thiol affinity columns. The identification of new modes of cell penetration is important because they promise new solutions to challenges in delivery and beyond. John Wiley and Sons Inc. 2019-06-06 2019-07-08 /pmc/articles/PMC6618005/ /pubmed/31168906 http://dx.doi.org/10.1002/anie.201905003 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. |
spellingShingle | Communications Cheng, Yangyang Zong, Lili López‐Andarias, Javier Bartolami, Eline Okamoto, Yasunori Ward, Thomas R. Sakai, Naomi Matile, Stefan Cell‐Penetrating Dynamic‐Covalent Benzopolysulfane Networks |
title | Cell‐Penetrating Dynamic‐Covalent Benzopolysulfane Networks |
title_full | Cell‐Penetrating Dynamic‐Covalent Benzopolysulfane Networks |
title_fullStr | Cell‐Penetrating Dynamic‐Covalent Benzopolysulfane Networks |
title_full_unstemmed | Cell‐Penetrating Dynamic‐Covalent Benzopolysulfane Networks |
title_short | Cell‐Penetrating Dynamic‐Covalent Benzopolysulfane Networks |
title_sort | cell‐penetrating dynamic‐covalent benzopolysulfane networks |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6618005/ https://www.ncbi.nlm.nih.gov/pubmed/31168906 http://dx.doi.org/10.1002/anie.201905003 |
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