Molecular Engineering of Fluorescent Penicillins for Molecularly Imprinted Polymer Assays
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- 作者：Elena Benito-Peñ ; a ; Marí ; a C. Moreno-Bondi ; Santiago Aparicio ; Guillermo Orellana ; Josefine Cederfur ; and Maria Kempe
- 刊名：Analytical Chemistry
- 出版年：2006
- 出版时间：March 15, 2006
- 年：2006
- 卷：78
- 期：6
- 页码：2019 - 2027
- 全文大小：340K
- 年卷期：v.78,no.6(March 15, 2006)
- ISSN：1520-6882
文摘
The interaction of seven novel fluorescent labeled 
-lactams with a library of six polymer materials molecularlyimprinted (MI) with penicillin G (PenG) has been evaluated using both radioactive and fluorescence competitiveassays. The highly fluorescent competitors (emissionquantum yields of 0.4-0.95) have been molecularlyengineered to contain pyrene or dansyl labels whilekeeping intact the 6-aminopenicillanic acid moiety forefficient recognition by the cross-linked polymers. Pyrenemethylacetamidopenicillanic acid (PAAP) is the taggedantibiotic that provides the highest selectivity when competing with PenG for the specific binding sites in a MIpolymer prepared with methacrylic acid and trimethylolpropane trimethacrylate (10:15 molar ratio) in acetonitrilein the presence of PenG. Molecular modeling shows thatrecognition of the fluorescent analogues of PenG by theMI material is due to a combination of size and shapeselectivity and demonstrates how critical the choice oflabel and tether chain is. PAAP has been applied to thedevelopment of a fluorescence competitive assay for PenGanalysis with a dynamic range of 3-890 
M in 99:1acetonitrile-water solution. Competitive binding studiesdemonstrate various degrees of cross-reactivity for someantibiotics derived from 6-aminopenicillanic acid, particularly amoxicillin, ampicillin, and penicillin V (but notoxacillin, cloxacillin, dicloxacillin, or nafcillin). Otherantibiotics, such as chloramphenicol, tetracycline, orcephapirin, do not compete with PAAP for binding to theimprinted polymer. The MI assay has successfully beentested for PenG analysis in a pharmaceutical formulation.
-lactams with a library of six polymer materials molecularlyimprinted (MI) with penicillin G (PenG) has been evaluated using both radioactive and fluorescence competitiveassays. The highly fluorescent competitors (emissionquantum yields of 0.4-0.95) have been molecularlyengineered to contain pyrene or dansyl labels whilekeeping intact the 6-aminopenicillanic acid moiety forefficient recognition by the cross-linked polymers. Pyrenemethylacetamidopenicillanic acid (PAAP) is the taggedantibiotic that provides the highest selectivity when competing with PenG for the specific binding sites in a MIpolymer prepared with methacrylic acid and trimethylolpropane trimethacrylate (10:15 molar ratio) in acetonitrilein the presence of PenG. Molecular modeling shows thatrecognition of the fluorescent analogues of PenG by theMI material is due to a combination of size and shapeselectivity and demonstrates how critical the choice oflabel and tether chain is. PAAP has been applied to thedevelopment of a fluorescence competitive assay for PenGanalysis with a dynamic range of 3-890 M in 99:1acetonitrile-water solution. Competitive binding studiesdemonstrate various degrees of cross-reactivity for someantibiotics derived from 6-aminopenicillanic acid, particularly amoxicillin, ampicillin, and penicillin V (but notoxacillin, cloxacillin, dicloxacillin, or nafcillin). Otherantibiotics, such as chloramphenicol, tetracycline, orcephapirin, do not compete with PAAP for binding to theimprinted polymer. The MI assay has successfully beentested for PenG analysis in a pharmaceutical formulation.