Molecular engineering of fluorescent penicillins for molecularly imprinted polymer assays

Analytical Chemistry
Elena Benito-PeñaMaria Kempe

Abstract

The interaction of seven novel fluorescent labeled beta-lactams with a library of six polymer materials molecularly imprinted (MI) with penicillin G (PenG) has been evaluated using both radioactive and fluorescence competitive assays. The highly fluorescent competitors (emission quantum yields of 0.4-0.95) have been molecularly engineered to contain pyrene or dansyl labels while keeping intact the 6-aminopenicillanic acid moiety for efficient recognition by the cross-linked polymers. Pyrenemethylacetamidopenicillanic acid (PAAP) is the tagged antibiotic that provides the highest selectivity when competing with PenG for the specific binding sites in a MI polymer prepared with methacrylic acid and trimethylolpropane trimethacrylate (10:15 molar ratio) in acetonitrile in the presence of PenG. Molecular modeling shows that recognition of the fluorescent analogues of PenG by the MI material is due to a combination of size and shape selectivity and demonstrates how critical the choice of label and tether chain is. PAAP has been applied to the development of a fluorescence competitive assay for PenG analysis with a dynamic range of 3-890 muM in 99:1 acetonitrile-water solution. Competitive binding studies demonstrate various degrees o...Continue Reading

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Citations

Oct 31, 2006·Analytical and Bioanalytical Chemistry·M A González-MartínezA Maquieira
Oct 12, 2010·Analytical and Bioanalytical Chemistry·Henrik Kempe, Maria Kempe
Oct 22, 2011·International Journal of Molecular Sciences·Giuseppe VasapolloGiuseppe Mele
Sep 8, 2015·Analytical and Bioanalytical Chemistry·Javier L UrracaMaria C Moreno-Bondi
May 21, 2008·Biosensors & Bioelectronics·Javier L UrracaMaría C Moreno-Bondi
Jul 25, 2009·Chemistry : a European Journal·Yi Ge, Anthony P F Turner
Apr 5, 2014·Journal of Molecular Recognition : JMR·Michael J WhitcombeIan A Nicholls
Nov 23, 2015·Analytical and Bioanalytical Chemistry·Thomas S Bedwell, Michael J Whitcombe
Sep 3, 2014·Journal of Pharmaceutical and Biomedical Analysis·Giovanni MerolaLuigi Campanella
Aug 12, 2014·Pharmaceutical Research·Henrik KempeMaria Kempe
Aug 12, 2016·Luminescence : the Journal of Biological and Chemical Luminescence·Paweł BerczyńskiHassan Y Aboul-Enein
Mar 5, 2016·Chemical Society Reviews·Lingxin ChenJinhua Li
May 1, 2015·Chemical Science·Sergio CarrascoMaría C Moreno-Bondi
Jun 22, 2010·Journal of the American Chemical Society·Marco FrasconiItamar Willner
Jan 24, 2008·Chemical Reviews·Radislav A Potyrailo, Vladimir M Mirsky

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