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Controlling Supramolecular Structures of Drugs by Light.
Wiest, Johannes Kehrein, Josef Saedtler, Marco Schilling, Klaus Cataldi, Eleonora Sotriffer, Christoph A Holzgrabe, Ulrike Rasmussen, Tim Böttcher, Bettina Cronin-Golomb, Mark
Wiest, Johannes
Kehrein, Josef
Saedtler, Marco
Schilling, Klaus
Cataldi, Eleonora
Sotriffer, Christoph A
Holzgrabe, Ulrike
Rasmussen, Tim
Böttcher, Bettina
Cronin-Golomb, Mark
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2020-10-29
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Adobe PDF, 1014.52 KB
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Abstract
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.
Citation
Mol Pharm. 2020 Oct 29. doi: 10.1021/acs.molpharmaceut.0c00720. Epub ahead of print.
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en
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1543-8392
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Attribution-NonCommercial-ShareAlike 4.0 International