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Updated: Jan 23, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Cell-Penetrating Dynamic-Covalent Benzopolysulfane Networks
Yangyang Cheng1, Lili Zong1,2, Javier López-Andarias1
1Department of Organic Chemistry, University of Geneva, Geneva, Switzerland.
Benzopolysulfanes (BPS) offer efficient cell penetration, bypassing common uptake inhibitors. These dynamic-covalent sulfur networks exhibit high reactivity and selectivity, enabling novel delivery pathways for large molecules.
Area of Science:
- Chemical Biology
- Materials Science
Background:
- Cyclic oligochalcogenides (COCs) are explored for cellular delivery.
- Existing COCs like diselenolanes and epidithiodiketopiperazines have limitations.
Purpose of the Study:
- Introduce benzopolysulfanes (BPS) as novel COCs for enhanced cellular delivery.
- Investigate the unique properties and mechanisms of BPS.
Main Methods:
- Synthesis and characterization of benzopolysulfanes (BPS).
- Assessment of BPS cellular uptake efficiency and pathways.
- Evaluation of BPS reactivity with thiols and stability.
Main Results:
- BPS demonstrate efficient cell penetration, independent of endocytosis inhibitors.
- BPS exhibit high reactivity towards thiols, exceeding disulfide exchange rates.
- BPS form dynamic-covalent networks of sulfur species, adaptable to cargo size.
- BPS show high retention on thiol affinity columns, unlike other COCs.
Conclusions:
- Benzopolysulfanes represent a new class of COCs with superior delivery capabilities.
- BPS's unique reactivity and network dynamics enable novel cellular uptake mechanisms.
- BPS hold promise for overcoming challenges in drug delivery and biomaterial applications.
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