posted on 2020-10-29, 16:23authored byJohannes Wiest, Josef Kehrein, Marco Saedtler, Klaus Schilling, Eleonora Cataldi, Christoph A. Sotriffer, Ulrike Holzgrabe, Tim Rasmussen, Bettina Böttcher, Mark Cronin-Golomb, Matthias Lehmann, Nathalie Jung, Mike Windbergs, Lorenz Meinel
Controlling
physicochemical properties of light-unresponsive drugs,
by light, prima facie, a paradox approach. We expanded light control
by ion pairing light-unresponsive salicylate or ibuprofen to photoswitchable
azobenzene counterions, thereby reversibly controlling supramolecular
structures, hence the drugs’ physicochemical and kinetic properties.
The resulting ion pairs photoliquefied into room-temperature ionic
liquids under ultraviolet light. Aqueous solutions showed trans–cis-dependent supramolecular structures under
a light with wormlike aggregates decomposing into small micelles and
vice versa. Light control allowed for permeation through membranes
of cis-ibuprofen ion pairs within 12 h in contrast
to the trans ion pairs requiring 72 h. In conclusion,
azobenzene ion-pairing expands light control of physicochemical and
kinetic properties to otherwise light-unresponsive drugs.