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Low-oxidation-potential thiophene-carbazole monomers for electro-oxidative molecular imprinting: Selective chemosensing of aripiprazole
Polish Acad Sci, Poland; Med Univ Warsaw, Poland.
Linköping University, Department of Science and Technology, Laboratory of Organic Electronics. Linköping University, Faculty of Science & Engineering. Cardinal Stefan Wyszynski Univ Warsaw, Poland.
Polish Acad Sci, Poland.
Med Univ Warsaw, Poland.
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2020 (English)In: Biosensors & bioelectronics, ISSN 0956-5663, E-ISSN 1873-4235, Vol. 169, article id 112589Article in journal (Refereed) Published
Abstract [en]

New thiophene-carbazole functional and cross-linking monomers electropolymerizing at potentials sufficiently low for molecular imprinting of an electroactive aripiprazole antipsychotic drug were herein designed and synthesized. Numerous conducting molecularly imprinted polymer (MIP) films are deposited by electro-polymerization at relatively low potentials by electm-oxidation of pyrmle, aniline, phenol, or 3,4-ethylenediox-ythiophene (EDOT). However, their interactions with templates are not sufficiently strong. Hence, it is necessary to introduce additional recognizing sites in these cavities to increase their affinity to the target molecules. For that, functional monomers derivatized with substituents forming stable complexes with the templates are used. However, oxidation potentials of these derivatives are often, disadvantageously, higher than that of parent monomers. Therefore, we designed and synthesized new functional and cross-linking monomers, which are oxidized at sufficiently low potentials. The deposited MIP and non-imprinted polymer (NIP) films were characterized by PM-IRRAS and UV-vis spectroscopy and imaged with AFM. The structure of the aripiprazole prepolymerization complex with functional monomers was optimized with density functional theory (DFT), and aripiprazole interactions with imprinted cavities were simulated with molecular mechanics (MM) and molecular dynamics (MD). MIP-aripiprazole film-coated electrodes were used as extended gates for selective determination of aripiprazole with the extended-gate field-effect transistor (EG-FET) chemosensor. The linear dynamic concentration range was 30-300 pM, and the limit of detection was 22 fM. An apparent imprinting factor of the MIP-1 was IF = 4.95. The devised chemosensor was highly selective to glucose, urea, and creatinine interferences. The chemosensor was successfully applied for aripiprazole determination in human plasma. The results obtained were compared to those of the validated HPLC-MS method.

Place, publisher, year, edition, pages
ELSEVIER ADVANCED TECHNOLOGY , 2020. Vol. 169, article id 112589
Keywords [en]
Molecularly imprinted polymer; Electropolymerization; Aripiprazole; Bioanalysis; Extended-gate field-effect transistor; Computer simulation
National Category
Analytical Chemistry
Identifiers
URN: urn:nbn:se:liu:diva-171462DOI: 10.1016/j.bios.2020.112589ISI: 000582395000014PubMedID: 32942142OAI: oai:DiVA.org:liu-171462DiVA, id: diva2:1502708
Note

Funding Agencies|National Science Center (NCN)National Science Center, PolandNational Science Centre, Poland [2015/19/B/ST4/03743]; NCN [2014/15/B/NZ7/01011]

Available from: 2020-11-20 Created: 2020-11-20 Last updated: 2020-11-20

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