title: New biosourced chiral molecularly imprinted polymer: Synthesis, characterization, and evaluation of the recognition capacity of methyltestosterone.
abstract: New biosourced chiral cross-linkers were reported for the first time in the synthesis of methyltestosterone (MT) chiral molecularly imprinted polymers (cMIPs). Isosorbide and isomannide, known as 1,4:3,6-dianhydrohexitols, were selected as starting diols. The cMIPs were synthesized following a noncovalent approach via thermal radical polymerization and monitored by Raman spectroscopy. These cross-linkers were fully characterized by1H and13C nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry. The cross-polarization magic angle spinning13C NMR, Fourier transform infrared spectroscopy, scanning electron microscopy, and specific surface areas following the Brunauer-Emmett-Teller (BET) method were used to characterize the cMIPs. The effect of stereochemistry of cross-linkers on the reactivity of polymerization, morphology, and adsorption-recognition properties of the MIP was evaluated. The results showed that the cMIP exhibited an obvious improvement in terms of rebinding capacity for MT as compared with the nonimprinted polymer (NIP). The highest binding capacity was observed for cMIP-Is (27.298 mg g-1) for high concentrations (500 mg L-1). However, the isomannide homologue cMIP-Im showed higher recovery-up to 65% and capacity for low concentrations (15 mg L-1). The experimental data were properly fitted by the Freundlich adsorption isothermal model.
authors.affiliation: Institute of Analytical Sciences, UMR 5280, CNRS, ENS-Lyon, University Lyon 1, Villeurbanne, France.|Laboratory of Natural Substances (LR10INRAP02), National Institute of Research and Physical and Chemical Analysis (INRAP), Sidi Thabet Biotechpole, Ariana, Tunisia.|Faculty of Sciences of Tunis, University of Tunis El Manar, Tunis, Tunisia.
authors.forename: Asma
authors.initials: A
authors.lastname: Saadaoui
authors.affiliation: Institute of Analytical Sciences, UMR 5280, CNRS, ENS-Lyon, University Lyon 1, Villeurbanne, France.
authors.forename: Corinne
authors.initials: C
authors.lastname: Sanglar
authors.affiliation: Laboratory of Natural Substances (LR10INRAP02), National Institute of Research and Physical and Chemical Analysis (INRAP), Sidi Thabet Biotechpole, Ariana, Tunisia.
authors.forename: Raouf
authors.identifier: 0000-0003-3105-5189
authors.initials: R
authors.lastname: Medimagh
authors.affiliation: Institute of Analytical Sciences, UMR 5280, CNRS, ENS-Lyon, University Lyon 1, Villeurbanne, France.
authors.forename: Anne
authors.initials: A
authors.lastname: Bonhomme
authors.affiliation: Institute of Analytical Sciences, UMR 5280, CNRS, ENS-Lyon, University Lyon 1, Villeurbanne, France.
authors.forename: Robert
authors.initials: R
authors.lastname: Baudot
authors.affiliation: Institute of Analytical Sciences, UMR 5280, CNRS, ENS-Lyon, University Lyon 1, Villeurbanne, France.
authors.forename: Saber
authors.initials: S
authors.lastname: Chatti
authors.affiliation: Institut Lavoisier de Versailles (ILV), UMR, CNRS 8180, University of Versailles-St-Quentin (UVSQ), Versailles Cedex, France.
authors.forename: Sylvain
authors.initials: S
authors.lastname: Marque
authors.affiliation: Institut Lavoisier de Versailles (ILV), UMR, CNRS 8180, University of Versailles-St-Quentin (UVSQ), Versailles Cedex, France.
authors.forename: Damien
authors.initials: D
authors.lastname: Prim
authors.affiliation: Faculty of Sciences of Tunis, University of Tunis El Manar, Tunis, Tunisia.
authors.forename: Mongia Saïd
authors.initials: MS
authors.lastname: Zina
authors.affiliation: Institute of Analytical Sciences, UMR 5280, CNRS, ENS-Lyon, University Lyon 1, Villeurbanne, France.
authors.forename: Herve
authors.initials: H
authors.lastname: Casabianca
mesh_terms: D008777:Methyltestosterone / Q000378:metabolism; D008855:Microscopy, Electron, Scanning; D054802:Molecular Imprinting / Q000379:methods*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D052616:Solid Phase Extraction; D017550:Spectroscopy, Fourier Transform Infrared; D013059:Spectrum Analysis, Raman; D013237:Stereoisomerism
chemical_list: D011108:Polymers; D008777:Methyltestosterone
keywords: 1,4:3,6-dianhydrohexitols; assisted solvent extraction; isosorbide; methyltestosterone; molecularly imprinted; stereoinduction