Cell-Penetrating Dynamic-Covalent Benzopolysulfane Networks

Cheng, Yangyang and Zong, Lili and Lopez-Andarias, Javier and Bartolami, Eline and Okamoto, Yasunori and Ward, Thomas R. and Sakai, Naomi and Matile, Stefan. (2019) Cell-Penetrating Dynamic-Covalent Benzopolysulfane Networks. Angewandte Chemie International Edition, 58 (28). pp. 9522-9526.

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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.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Bioanorganische Chemie (Ward)
UniBasel Contributors:Ward, Thomas R. R.
Item Type:Article, refereed
Article Subtype:Research Article
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:29 Oct 2019 10:55
Deposited On:29 Oct 2019 10:55

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