Details

Autor(en) / Beteiligte

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

Titel

Cell‐Penetrating Dynamic‐Covalent Benzopolysulfane Networks

Ist Teil von

• Angewandte Chemie (International ed.), 2019-07, Vol.58 (28), p.9522-9526

Auflage

International ed. in English

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2019

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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. One ring to rule them all: Benzopolysulfanes are introduced as the “lord of the rings” with regard to cell‐penetrating cyclic oligochalcogenides, acting through an intriguing, in situ generated dynamic‐covalent network of extreme sulfur species, including oligomers with up to nineteen sulfur atoms in one macrocycle, that excels with very high reactivity, selectivity as well as affinity to thiols.