@article{10272/21709,
year = {2022},
url = {https://hdl.handle.net/10272/21709},
abstract = {The cucurbit[8]uril (CB8) synthetic receptor is shown to form high-affinity host–guest complexes with dicationic dithienylethene (DTE) photoswitches in water. ITC experiments combined with computational studies suggest that the formation of the inclusion complexes is mainly driven by a combination of hydrophobic effects, ion–dipole, hydrogen- and chalcogen-bonding interactions. The binding affinities were observed to be much higher for the DTE closed isomers, reaching values in the picomolar range (up to 1011 M−1) while the open isomers display up to 10 000-fold lower affinities, setting ideal conditions for the development of robust photoswitchable host–guest complexes. The light-responsive affinity of these photoswitches toward CB8 was explored to control the encapsulation and release of nanomolar affinity steroids via competitive guest replacement.},
organization = {This work was supported by the Associate Laboratory for Green
Chemistry – LAQV (projects UIDB/50006/2020 and UIDP/
50006/2020), the Research Unit on Applied Molecular
Biosciences – UCIBIO (projects UIDP/04378/2020 and UIDB/
04378/2020) and the Associate Laboratory Institute for Health
and Bioeconomy – i4HB (project LA/P/0140/2020) which are
financed by national funds from FCT/MCTES. FCT/MCTES is
also acknowledged for supporting the National Portuguese
NMR Network (ROTEIRO/0031/2013–PINFRA/22161/2016, cofinanced
by FEDER through COMPETE 2020, POCI, PORL, and
FCT through PIDDAC) and for the grants PTDC/QUI-COL/
32351/2017 (NB), PTDC/QUI-QFI/30951/2017 (AJP), FCT-ANR/
BBB-MET/0023/2012 (SRP), PTDC/BIA-BQM/29442/2017 (SRP),
CEECIND/00466/2017 (NB) and 2021.07205.BD (MC).
European Commission is acknowledged for the INFUSION
project grant N. 734834 under H2020-MSCA-RISE-2016. PJC
acknowledges FCT for the CEECIND 2021 Initiative (CEECIND/
00381/2021) and strategic projects UIDB/04046/2020-UIDP/
04046/2020 (BioISI). UP thanks the Spanish Ministry of
Science and Innovation for financial support (project
PID2020-119992GB-I00).},
publisher = {Royal Society of Chemistry},
title = {Photomodulation of ultrastable host–guest complexes in water and their application in light-controlled steroid release},
doi = {10.1039/d2qo00423b},
author = {Máximo, Patrícia and Colaço, Miriam and Pauleta, Sofia R. and Costa, Paulo J. and Pischel, Uwe and Parola, A. Jorge and Basílio, Nuno},
}