American Chemical Society
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Controlling Supramolecular Structures of Drugs by Light

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posted on 2020-10-29, 16:23 authored by Johannes 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.