Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
4 years ago

Morphology-Dependent Cell Imaging by Using a Self-Assembled Diacetylene Peptide Amphiphile

Morphology-Dependent Cell Imaging by Using a Self-Assembled Diacetylene Peptide Amphiphile
Carsten Schmuck, Eilo Zellermann, Xiao-Yu Hu, Hao Jiang, Mao Li, Shirley K. Knauer, Stefanie Schlesiger
Herein, a novel cationic peptide gemini amphiphile containing diacetylene motifs (DA2P) is presented, which self-assembles into novel tadpole- and bola-shaped nanostructures at low concentrations and nanofibers at higher concentrations. Interestingly, the DA2P assemblies can be polymerized into a fluorescent red phase but only during incubation with HeLa cells, most likely owing to the reorganization of the diacetylene chains of DA2P upon interaction with the cell membrane. The red-fluorescent polymerized DA2P assemblies can serve as a novel cell imaging probe. However, only vesicles, tadpole- and bola-shaped DA2P assemblies can be translocated into HeLa cells, whereas the nanofiber-like DA2P assemblies are trapped by the cell membranes and do not enter the cells. Hence, morphology-dependent cell imaging is observed. Novel nanostructure: A peptide gemini amphiphile containing diacetylene motifs self-assembles into novel tadpole- and bola-shaped nanostructures at low concentrations, as well as nanofibers at higher concentrations. Interestingly, morphology-dependent cell imaging is achieved owing to the polymerization of the diacetylenes upon interaction with the cell membrane.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201708168

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