A molecularlyimprintedpolymer(MIP)wasdesignedandsynthesizedtoserveasafunctionalmaterial for selectiverecognitionof6-thioguanine(6TG),anantitumordrug.Forthat,thenewlysynthesized functional monomer,cytosine-bis(2,2′-bithienyl)-(4-carboxyphenyl)methaneester(Cyt-S4),revealed Watson–Crick typenucleobasepairingof6TG.FormationoftheCyt-S4and6TGcomplexofthe2:1 stoichiometry waspostulatedbasedontheDFTcalculationsattheB3LYP/3-21G(n) levelandexperi- mentally confirmed by fluorescence titration.Themolecularlyimprintedpolymer(MIP) film wasde- posited bypotentiodynamicelectropolymerizationonaPtdiskelectrodeaswellasonanAu-coatedglass slide andonanAu-quartzcrystalresonator.Thestatisticalmodelofformationofthis film wassuc- cessfully simulatedbymoleculardynamics.Completenessofthesubsequent6TGtemplateextraction from MIPwasconfirmed bytheUV–visible spectroscopy.Animprintingfactorof2.9fortheMIP film was determined bypiezoelectricmicrogravimetryusingECQM.Thedouble-layercapacityandalternating current measurementsunder flow-injectionanalysis(FIA)conditionswereselectedtotransducethe6TG recognition signalintothechangeofthedouble-layercapacitydependenceonthe6TGconcentrationin solution fordifferentsupportingelectrolyteconcentrations.Detectabilityoftheresultingchemosensor was10 mM 6TGforthe0.5MKFcarriersolutioninFIA.Selectivityofthechemosensorwithrespectto common interferenceswashigh,e.g.,itexceeded130to2-amino-6-methylmercaptopurine,a6TGme- tabolite.
Cytosinederivatizedbis(2,2′-bithienyl)methanemolecularlyimprinted polymerforselectiverecognitionof6-thioguanine,anantitumordrug
BENINCORI, TIZIANA;
2015-01-01
Abstract
A molecularlyimprintedpolymer(MIP)wasdesignedandsynthesizedtoserveasafunctionalmaterial for selectiverecognitionof6-thioguanine(6TG),anantitumordrug.Forthat,thenewlysynthesized functional monomer,cytosine-bis(2,2′-bithienyl)-(4-carboxyphenyl)methaneester(Cyt-S4),revealed Watson–Crick typenucleobasepairingof6TG.FormationoftheCyt-S4and6TGcomplexofthe2:1 stoichiometry waspostulatedbasedontheDFTcalculationsattheB3LYP/3-21G(n) levelandexperi- mentally confirmed by fluorescence titration.Themolecularlyimprintedpolymer(MIP) film wasde- posited bypotentiodynamicelectropolymerizationonaPtdiskelectrodeaswellasonanAu-coatedglass slide andonanAu-quartzcrystalresonator.Thestatisticalmodelofformationofthis film wassuc- cessfully simulatedbymoleculardynamics.Completenessofthesubsequent6TGtemplateextraction from MIPwasconfirmed bytheUV–visible spectroscopy.Animprintingfactorof2.9fortheMIP film was determined bypiezoelectricmicrogravimetryusingECQM.Thedouble-layercapacityandalternating current measurementsunder flow-injectionanalysis(FIA)conditionswereselectedtotransducethe6TG recognition signalintothechangeofthedouble-layercapacitydependenceonthe6TGconcentrationin solution fordifferentsupportingelectrolyteconcentrations.Detectabilityoftheresultingchemosensor was10 mM 6TGforthe0.5MKFcarriersolutioninFIA.Selectivityofthechemosensorwithrespectto common interferenceswashigh,e.g.,itexceeded130to2-amino-6-methylmercaptopurine,a6TGme- tabolite.
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