Supramolecular Atropine Potentiometric Sensor

A supramolecular atropine sensor was developed, using cucurbit[6]uril as the recognition element. The solid-contact electrode is based on a polymeric membrane incorporating cucurbit[6]uril (CB[6]) as an ionophore, 2-nitrophenyl octyl ether as a solvent mediator, and potassium tetrakis (4-chlorophenyl) borate as an additive. In a MES-NaOH buffer at pH 6, the performance of the atropine sensor is characterized by a slope of (58.7 ± 0.6) mV/dec with a practical detection limit of (6.30 ± 1.62) × 10−7 mol/L and a lower limit of the linear range of (1.52 ± 0.64) × 10−6 mol/L. Selectivity coefficients were determined for different ions and excipients. The obtained results were bolstered by the docking and spectroscopic studies which demonstrated the interaction between atropine and CB[6]. The accuracy of the potentiometric analysis of atropine content in certified reference material was evaluated by the t-Student test. The herein proposed sensor answers the need for reliable methods providing better management of this hospital drug shelf-life while reducing its flush and remediation costs.

[1]  K. Vytras.  The use of ion-selective electrodes in the determination of drug substances. , 1989, Journal of pharmaceutical and biomedical analysis.

[2]  Bert L. de Groot,et al.  Ligand docking and binding site analysis with PyMOL and Autodock/Vina , 2010, J. Comput. Aided Mol. Des..

[3]  M. A. Silva,et al.  Physicochemical Properties and Dissolution Studies of Dexamethasone Acetate-β-Cyclodextrin Inclusion Complexes Produced by Different Methods , 2008, AAPS PharmSciTech.

[4]  W. Nau,et al.  Cucurbiturils: from synthesis to high-affinity binding and catalysis. , 2015, Chemical Society reviews.

[5]  Z. Su,et al.  Guest exchange in a porous cucurbit[6]uril-based metal-organic rotaxane framework probed by NMR and X-ray crystallography. , 2018, Chemical communications.

[6]  Mohammad Mahdi Jaghoori,et al.  1001 Ways to run AutoDock Vina for virtual screening , 2016, Journal of Computer-Aided Molecular Design.

[7]  R. A. Dar,et al.  Electrochemical determination of atropine at multi-wall carbon nanotube electrode based on the enhancement effect of sodium dodecyl benzene sulfonate. , 2012, Colloids and surfaces. B, Biointerfaces.

[8]  J. Alvarez,et al.  Drugs Involved in Drug-Facilitated Crime—Pharmacological Aspects , 2014 .

[9]  Yunqian Zhang,et al.  Synthesis and X-ray structure of the inclusion complex of dodecamethylcucurbit[6]uril with 1,4-dihydroxybenzene. , 2007, Molecules.

[10]  Yebang Tan,et al.  Fabrication and properties of cucurbit[6]uril induced thermo-responsive supramolecular hydrogels , 2009 .

[11]  Jianzhuang Jiang,et al.  X-ray structure of a porphyrin-tetramethylcucurbit[6]uril supramolecular polymer. , 2013, Chemistry.

[12]  G. Mostafa,et al.  PVC Membrane Sensor for Potentiometric Determination of Atropine in Some Pharmaceutical Formulations , 2008 .

[13]  V. Fedin,et al.  Kinetic trapping of the host-guest association intermediate and its transformation into a thermodynamic inclusion complex. , 2013, Chemical communications.

[14]  S. Hassan,et al.  New liquid-membrane electrodes for direct determination of atropine in pharmaceutical preparations. , 1987, Talanta.

[15]  L. Lindoy,et al.  Synthesis and separation of cucurbit[n]urils and their derivatives. , 2016, Organic & biomolecular chemistry.

[16]  T. Kučera,et al.  Interaction of Cucurbit[7]uril with Oxime K027, Atropine, and Paraoxon: Risky or Advantageous Delivery System? , 2020, International journal of molecular sciences.

[17]  G. J. Moody,et al.  Characterisation of poly(vinyl chloride) barium ion-selective electrodes without an internal reference solution , 1988 .

[18]  Yuan Zhao,et al.  Computation of Octanol-Water Partition Coefficients by Guiding an Additive Model with Knowledge , 2007, J. Chem. Inf. Model..

[19]  S. Hassan,et al.  Liquid and poly(vinyl chloride) atropine-reineckate membrane electrodes for determination of atropine. , 1984, Analytical chemistry.

[21]  Oksana Danylyuk,et al.  Host–guest complexes of cucurbit[6]uril with phenethylamine-type stimulants , 2018 .

[22]  Weijun Zhou,et al.  A descent modified Polak–Ribière–Polyak conjugate gradient method and its global convergence , 2006 .

[23]  Jae Wook Lee,et al.  Cucurbituril homologues and derivatives: new opportunities in supramolecular chemistry. , 2003, Accounts of chemical research.

[24]  Jonathan P. Metters,et al.  Forensic electrochemistry: sensing the molecule of murder atropine. , 2013, The Analyst.

[25]  M. Zareh.  Atropine-selective membrane electrodes and relative selectivity concept. , 2008, Analytical sciences : the international journal of the Japan Society for Analytical Chemistry.

[26]  V. Fedin,et al.  Host–guest complexes of cucurbit[6]uril with isoprenaline: the effect of the metal ion on the crystallization pathway and supramolecular architecture , 2013 .

[27]  M. Hearn,et al.  One-pot oxidative N-demethylation of tropane alkaloids with hydrogen peroxide and a FeIII-TAML catalyst , 2012 .

[28]  F. Allen,et al.  Institutional profile: Crystal structure information in drug discovery and development: current perspectives and new possibilities from the Cambridge Crystallographic Data Centre. , 2010, Future medicinal chemistry.

[29]  J. Lima,et al.  Construction and Evaluation of Atropine Selective Electrodes. Their Application to Ophthalmic Formulations , 1994 .

[30]  M. Kralj,et al.  Photodeamination to quinone methides in cucurbit[n]urils: potential application in drug delivery. , 2018, Organic & biomolecular chemistry.

[31]  Kimoon Kim,et al.  Cucurbit[n]uril Derivatives Soluble in Water and Organic Solvents. , 2001, Angewandte Chemie.

[32]  J. Lima,et al.  A phenobarbital ion-selective electrode without an inner reference solution, and its application to pharmaceutical analysis. , 1990, Journal of pharmaceutical and biomedical analysis.

[33]  G. Greenway,et al.  Chemiluminescence muTAS for the determination of atropine and pethidine. , 2002, Talanta.

[34]  A. Palmeira,et al.  Interaction between hydroxyethyl starch and propofol: computational and laboratorial study , 2014, Journal of biomolecular structure & dynamics.

[35]  Lyle Isaacs,et al.  The cucurbit[n]uril family. , 2005, Angewandte Chemie.

[36]  Evan Bolton,et al.  PubChem 2019 update: improved access to chemical data , 2018, Nucleic Acids Res..

[37]  Matthew L. Danielson,et al.  Computer-aided drug design platform using PyMOL , 2011, J. Comput. Aided Mol. Des..

[38]  M. Baker,et al.  UTILISATION OF AN ELECTROCHEMILUMINESCENCE SENSOR FOR ATROPINE DETERMINATION IN COMPLEX MATRICES. , 2019, Analytical chemistry.

[39]  Mohsen M Zareh,et al.  Phosphorated calix[6]arene derivatives as an ionophore for atropine-selective membrane electrodes. , 2007, Journal of AOAC International.

[40]  Renato L. Gil,et al.  Study of a novel bisnaphthalimidopropyl polyamine as electroactive material for perchlorate-selective potentiometric sensors. , 2015 .

[41]  I. Khokhar,et al.  SPECTROPHOTOMETRIC DETERMINATION OF ATROPINE , 1994 .

[42]  A. Coleman,et al.  Host-guest complexes of local anesthetics with cucurbit[6]uril and para-sulphonatocalix[8]arene in the solid state , 2017 .