Synthesis and binding studies of two new coumarin-squaramide-based receptors for NSAIDs
Luca Mancini, Filippo Ingargiola, Giampaolo Barone, Patrizia Rossi, Mauro Formica, Eleonora Macedi, Martina Lippi, Luca Giorgi, Luca Prodi, Vieri Fusi, Daniele Paderni
TL;DR
Scientists created new coumarin-squaramide molecules that can bind to anti-inflammatory drugs, using hydrogen bonds and aromatic interactions.
Contribution
The paper introduces two new coumarin-squaramide receptors specifically designed for NSAID anions.
Findings
L1 forms 2:1 ligand-to-anion adducts, while L2 forms 1:1 adducts with NSAID anions.
The receptors interact with NSAID carboxylates via hydrogen bonding and π-stacking.
UV-Vis, fluorescence, and NMR studies confirmed the binding ability of the receptors.
Abstract
Two new squaramide-based receptors containing coumarin units have been synthesized and characterized in both solution and solid states. L1 (3-(benzylamino)-4-((2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl)amino)cyclobut-3-ene-1,2-dione) is a linear molecule, while L2 (4,4′-((1,3-phenylenebis(methylene))bis(azanediyl))bis(3-((2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl)amino)cyclobut-3-ene-1,2-dione)) is an open chain ligand which results in the ditopic form of the simpler parent ligand L1. The new molecules have been designed to act as receptors for non-steroidal anti-inflammatory drugs (NSAIDs) possessing both squaramide units as double hydrogen bond (HB) donor sites that are able to interact with the carboxylate functions of the guests, and 4-trifluoromethylcoumarin moieties as aromatic photoactive domains to facilitate π-stacking or hydrophobic interactions with the drug's aromatic rings.…
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Taxonomy
TopicsMolecular Sensors and Ion Detection · Crystallography and molecular interactions · Supramolecular Chemistry and Complexes