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

Abstract

Herein, a novel cationic peptide gemini amphiphile containing diacetylene motifs (DA P) is presented, which self-assembles into novel tadpole- and bola-shaped nanostructures at low concentrations and nanofibers at higher concentrations. Interestingly, the DA P 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 DA P upon interaction with the cell membrane. The red-fluorescent polymerized DA P assemblies can serve as a novel cell imaging probe. However, only vesicles, tadpole- and bola-shaped DA P assemblies can be translocated into HeLa cells, whereas the nanofiber-like DA P assemblies are trapped by the cell membranes and do not enter the cells. Hence, morphology-dependent cell imaging is observed.

Covalently Linked Perylene Diimide–Polydiacetylene Nanofibers Display Enhanced Stability and Photocurrent with Reversible FRET Phenomenon

“…We recently described a new strategy for fabrication of patterned conducting polymers and magnetic nanoparticles that takes advantage of the photopolymerization property of self‐assembled diacetylenes (DA). It is well known that topochemical polymerization of self‐assembled DAs leads to formation of polydiacetylene (PDA) . Because DAs are typically soluble in most organic solvents and PDAs are not, non‐UV‐irradiated parts of films created in this manner can be removed by utilizing a solvent development protocol.…”

Design and evaluation of ionizable peptide amphiphiles for siRNA delivery

“…Peptides coupled to lipophilic tails are promising delivery agents for various types of therapeutic compounds, as they spontaneously self-assemble into highly ordered supramolecular structures. [1][2][3][4] Despite promise in drug delivery, [4] they are only poorly studied as delivery agents for nucleic acids, with one notable exception of intracranial administration of siRNA-Peptide Nanofiber complexes. [5] Recently, we published new nanomaterials obtained from photopolymerized polydiacetylenic (PDA) surfactants that are forming diverse auto-organized structures.…”

Colloidally Stable Monolayer Nanosheets with Colorimetric Responses

“…Moreover, the PDA‐EDMA‐TMG nanosheet dispersion exhibits blue‐to‐red phase transition upon heating (Figure S7, Supporting Information). Similar to other PDA supramolecules, this process is accompanied by the generation of fluorescence (Figure S8, Supporting Information), which enables the direct observation of nanosheets by fluorescence microscopy (Figure f). The high‐resolution TEM image and corresponding selected‐area electron diffraction (SAED) pattern (Figure c) reveal that the nanosheets are noncrystalline, which is also supported by powder X‐ray diffraction (XRD) (Figure S9, Supporting Information).…”