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      Potentiometric Sensing of Nonsteroidal Painkillers by Acyclic Squaramide Ionophores

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          Abstract

          We report here a small library of a new type of acyclic squaramide receptors ( L1L5) as selective ionophores for the detection of ketoprofen and naproxen anions (KF and NS , respectively) in aqueous media. 1H NMR binding studies show a high affinity of these squaramide receptors toward KF and NS , suggesting the formation of H-bonds between the two guests and the receptors through indole and −NH groups. Compounds L1L5 have been tested as ionophores for the detection of KF and NS inside solvent PVC-based polymeric membranes. The optimal membrane compositions were established through the careful variation of the ligand/tridodecylmethylammonium chloride (TDMACl) anion-exchanger ratio. All of the tested acyclic squaramide receptors L1L5 have high affinity toward KF and NS and anti-Hofmeister selectivity, with L4 and L5 showing the highest sensitivity and selectivity to NS . The utility of the developed sensors for a high precision detection of KF in pharmaceutical compositions with low relative errors of analysis (RSD, 0.99–1.4%) and recoveries, R%, in the range 95.1–111.8% has been demonstrated. Additionally, the chemometric approach has been involved to effectively discriminate between the structurally very similar KF and NS , and the possibility of detecting these analytes at concentrations as low as 0.07 μM with R 2 of 0.947 and at 0.15 μM with R 2 of 0.919 for NS and KF , respectively, was shown.

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          Most cited references65

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          Determining association constants from titration experiments in supramolecular chemistry.

          The most common approach for quantifying interactions in supramolecular chemistry is a titration of the guest to solution of the host, noting the changes in some physical property through NMR, UV-Vis, fluorescence or other techniques. Despite the apparent simplicity of this approach, there are several issues that need to be carefully addressed to ensure that the final results are reliable. This includes the use of non-linear rather than linear regression methods, careful choice of stoichiometric binding model, the choice of method (e.g., NMR vs. UV-Vis) and concentration of host, the application of advanced data analysis methods such as global analysis and finally the estimation of uncertainties and confidence intervals for the results obtained. This tutorial review will give a systematic overview of all these issues-highlighting some of the key messages herein with simulated data analysis examples.
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            The death of the Job plot, transparency, open science and online tools, uncertainty estimation methods and other developments in supramolecular chemistry data analysis.

            Data analysis is central to understanding phenomena in host-guest chemistry. We describe here recent developments in this field starting with the revelation that the popular Job plot method is inappropriate for most problems in host-guest chemistry and that the focus should instead be on systematically fitting data and testing all reasonable binding models. We then discuss approaches for estimating uncertainties in binding studies using case studies and simulations to highlight key issues. Related to this is the need for ready access to data and transparency in the methodology or software used, and we demonstrate an example a webportal () that aims to address this issue. We conclude with a list of best-practice protocols for data analysis in supramolecular chemistry that could easily be translated to other related problems in chemistry including measuring rate constants or drug IC50 values.
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              Squaramides: physical properties, synthesis and applications.

              Squaramides are remarkable four-membered ring systems derived from squaric acid that are able to form up to four hydrogen bonds. A high affinity for hydrogen bonding is driven through a concomitant increase in aromaticity of the ring. This hydrogen bonding and aromatic switching, in combination with structural rigidity, have been exploited in many of the applications of squaramides. Substituted squaramides can be accessed via modular synthesis under relatively mild or aqueous conditions, making them ideal units for bioconjugation and supramolecular chemistry. In this tutorial review the fundamental electronic and structural properties of squaramides are explored to rationalise the geometry, conformation, reactivity and biological activity.
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                Author and article information

                Journal
                ACS Sens
                ACS Sens
                se
                ascefj
                ACS Sensors
                American Chemical Society
                2379-3694
                02 August 2023
                25 August 2023
                : 8
                : 8
                : 3225-3239
                Affiliations
                []Dipartimento di Scienze Chimiche e Geologiche, Università degli Studi di Cagliari , S.S. 554 Bivio per Sestu, 09042 Monserrato (CA), Italy
                []Department of Chemical Science and Technologies, University of Rome “Tor Vergata” , 00133 Rome, Italy
                [§ ]Department of Electronic Engineering, University of Rome “Tor Vergata” , 00133 Rome, Italy
                Author notes
                Author information
                https://orcid.org/0000-0002-4302-0234
                https://orcid.org/0000-0001-8093-576X
                https://orcid.org/0000-0002-0543-4348
                https://orcid.org/0000-0002-2380-1404
                https://orcid.org/0000-0002-1137-6973
                Article
                10.1021/acssensors.3c00981
                10463271
                37530141
                3d1ba464-e46d-4613-b12d-1c8171844e66
                © 2023 The Authors. Published by American Chemical Society

                Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained ( https://creativecommons.org/licenses/by/4.0/).

                History
                : 17 May 2023
                : 06 July 2023
                Funding
                Funded by: Muir Maxwell Trust, doi 10.13039/501100019741;
                Award ID: 2017EKCS35
                Funded by: European Union Next Generation EU National Recovery and Resilience Plan, doi NA;
                Award ID: PE0000005
                Funded by: Universita` degli Studi di Cagliari, doi NA;
                Award ID: FIR 2016- 2019
                Categories
                Article
                Custom metadata
                se3c00981
                se3c00981

                squaramides,potentiometric sensing ion-selective electrodes,anion recognition,emerging pollutants,supramolecular chemistry

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