AUTHOR=Vurro Vito , Bondelli Gaia , Sesti Valentina , Lodola Francesco , Paternò Giuseppe Maria , Lanzani Guglielmo , Bertarelli Chiara TITLE=Molecular Design of Amphiphilic Plasma Membrane-Targeted Azobenzenes for Nongenetic Optical Stimulation JOURNAL=Frontiers in Materials VOLUME=7 YEAR=2021 URL=https://www.frontiersin.org/journals/materials/articles/10.3389/fmats.2020.631567 DOI=10.3389/fmats.2020.631567 ISSN=2296-8016 ABSTRACT=

We present a series of cationic membrane-targeted azobenzene molecules, with the aim to understand how variations in molecular architecture influence the relative optical and biological properties. 1,4-Amino-substituted azobenzene was chosen as the switching unit while the number of linked alkyl chains and their cationic end-group were systematically varied. Their photophysics, membrane partitioning, and electrophysiological efficacy were studied. We found that the polar end group is a key-factor determining the interaction with the phospholipid heads in the plasma membrane bilayer and consequently the ability to dimerize. The monosubstituted photoswitch with a pyridinium-terminated alkyl chain was found to be the best candidate for photostimulation. This study provides a structure-property investigation that can guide the chemical engineering of a new generation of molecular photo-actuators.