Cell‐Penetrating Dynamic‐Covalent Benzopolysulfane Networks

Abstract: 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.

Object Details

• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch

References and Relationships

• Bibliographic citation: Cell‐Penetrating Dynamic‐Covalent Benzopolysulfane Networks ; volume:131 ; number:28 ; year:2019 ; pages:9622-9626 ; extent:5 ; Angewandte Chemie ; 131, Heft 28 (2019), 9622-9626 (gesamt 5)

Contributors, Places and Time

• Creator: Cheng, Yangyang ; Zong, Lili ; López‐Andarias, Javier ; Bartolami, Eline ; Okamoto, Yasunori ; Ward, Thomas R. ; Sakai, Naomi ; Matile, Stefan

Further information

• DOI: 10.1002/ange.201905003
• URN: urn:nbn:de:101:1-2022080407192789198607
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 15.08.2025, 7:32 AM CEST