Photoswitchable Conjugated Oligoelectrolytes for a Light‐Induced Change of Membrane Morphology

The synthesis of a new conjugated oligoelectrolyte (COE), namely DSAzB, is described, which contains a conjugated core bearing a diazene moiety in the center of its electronically delocalized structure. Similar to structurally related phenylenevinylene‐based COEs, DSAzB readily intercalates into mod...

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Bibliographic Details
Published in:Angewandte Chemie 2020-11, Vol.132 (46), p.20513-20517
Main Authors: Leifert, Dirk, Moreland, Alex S., Limwongyut, Jakkarin, Mikhailovsky, Alexander A., Bazan, Guillermo C.
Format: Article
Language:English
Subjects:
actuators
biocatalysis
Calcein
Catalysis
Chemistry
conjugated oligoelectrolytes
Iodides
Irradiation
Isomerization
Lipid bilayers
Lipids
membrane permeabilization
Membranes
Morphology
photoswitches
Propidium iodide
Radiation
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Summary:The synthesis of a new conjugated oligoelectrolyte (COE), namely DSAzB, is described, which contains a conjugated core bearing a diazene moiety in the center of its electronically delocalized structure. Similar to structurally related phenylenevinylene‐based COEs, DSAzB readily intercalates into model and natural lipid bilayer membranes. Photoinduced isomerization transforms the linear trans COE into a bent or C‐shape form. It is thereby possible to introduce DSAzB into the bilayer of a cell and disrupt its integrity by irradiation with light. This leads to controlled permeabilization of membranes, as demonstrated by the release of calcein from DMPG/DMPC vesicles and by propidium iodide influx experiments on S. epidermidis. Both experiments support that the permeabilization is selective for the light stimulus, highly efficient, and repeatable. Target‐selective and photoinduced actions demonstrated by DSAzB may have broad applications in biocatalysis and related biotechnologies. Conjugated oligoelectrolytes (COEs) readily intercalate into model and natural lipid bilayer membranes. By introducing an azobenzene moiety into their backbone these COEs can be isomerized within the bilayer. This structural change of the COE leads to permeabilization of the membrane.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202004448