Photodeamination to quinone methides in cucurbit[n]urils: potential application in drug deliveryElectronic supplementary information (ESI) available: General experimental procedures, protonation constants for prototropic forms of 1 and 2, UV-vis spectra of 1 and 2 in the presence of CB[6] and CB[7], NMR titration experiments, NOESY spectra, molecular modeling data, isothermal microcalorimetric titration data, laser flash photolysis data and antiproliferative tests. See DOI: 10.1039/c8ob02605j

• Main Authors: Škalamera, ani, Matkovi, Marija, Uzelac, Lidija, Kralj, Marijeta, Mlinari -Majerski, Kata, Bohne, Cornelia, Basari, Nikola
• Format: Article
• Language: English
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c8ob02605j

We demonstrate a proof of principle for a new approach in the development of a drug delivery system. A positively charged prodrug (phenol) can form a stable inclusion complex with CB[7], which enables more efficient delivery of the prodrug. After photochemical transformation (photoactivation) inside the complex, an active drug quinone methide (QM) is formed and released from the complex, since it is a neutral molecule and forms a less stable complex with CB[7]. A prodrug is encapsulated in CB[7] and is photochemically transformed into an active drug inside this supramolecular complex.