Citation: Brandon Bishop, Shaofeng Huang, Hongxuan Chen, Haijia Yu, Hai Long, Jingshi Shen, Wei Zhang. Artificial transmembrane channel constructed from shape-persistent covalent organic molecular cages capable of ion and small molecule transport[J]. Chinese Chemical Letters, ;2024, 35(11): 109966. doi: 10.1016/j.cclet.2024.109966 shu

Artificial transmembrane channel constructed from shape-persistent covalent organic molecular cages capable of ion and small molecule transport

Brandon Bishop ^{a, 1} ,
Shaofeng Huang ^{a, 1} ,
Hongxuan Chen ^a ,
Haijia Yu ^b ,
Hai Long ^c ,
Jingshi Shen ^b ,
Wei Zhang ^{a, *,}

a.
Department of Chemistry, University of Colorado Boulder, Boulder, CO 80309, United States
b.
Department of Molecular, Cellular and Developmental Biology, University of Colorado Boulder, Boulder, CO 80309, United States
c.
National Renewable Energy Laboratory, Golden, CO 80401, United States

wei.zhang@colorado.edu

Received Date: 9 February 2024
Revised Date: 19 April 2024
Accepted Date: 5 May 2024
Available Online: 6 May 2024

Figures(4)

Shape-persistent arylene ethynylene molecular cages have been investigated as transmembrane channels for ions and small molecules. The molecular cages were obtained starting from tetrayne monomers through alkyne metathesis cyclooligomerization. We found these porphyrin-based rigid molecular cages can insert into the lipid bilayer and efficiently transport ions and small molecules (e.g., calcein). Our study reveals longer hydrophobic alkyl chains on the cage molecule promote the channeling efficiency, while shorter and/or more polar side chains impair such activity. Kinetic analysis shows linear correlation between the rate of proton transport and the concentration of the cage, suggesting the active species is likely a monomeric cage. We found that C₇₀-encapsulated cages are nearly inactive for transmembrane ion transportation, indicating that ions are likely transported through the internal cavity of the cage. Discrete shape-persistent organic cages represent highly stable synthetic ion channels or pores, which could have interesting applications in biomimetic signaling and drug delivery.
- Alkyne metathesis,
- Molecular cage,
- Transmembrane transportation,
- Dynamic covalent chemistry,
- Cell imaging
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