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Molecular engineering of fluorescent penicillins for molecularly imprinted polymer assays

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Author

  • E Benito-Pena
  • MC Moreno-Bondi
  • S Aparicio
  • G Orellana
  • Josefine Cederfur
  • Maria Kempe

Summary, in English

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 mu M in 99:1 acetonitrile-water solution. Competitive binding studies demonstrate various degrees of cross-reactivity for some antibiotics derived from 6-aminopenicillanic acid, particularly amoxicillin, ampicillin, and penicillin V (but not oxacillin, cloxacillin, dicloxacillin, or nafcillin). Other antibiotics, such as chloramphenicol, tetracycline, or cephapirin, do not compete with PAAP for binding to the imprinted polymer. The MI assay has successfully been tested for PenG analysis in a pharmaceutical formulation.

Publishing year

2006

Language

English

Pages

2019-2027

Publication/Series

Analytical Chemistry

Volume

78

Issue

6

Document type

Journal article

Publisher

The American Chemical Society (ACS)

Topic

  • Analytical Chemistry

Status

Published

Research group

  • Nanomedicine and Biomaterials

ISBN/ISSN/Other

  • ISSN: 1520-6882