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Molecular engineering of fluorescent penicillins for molecularly imprinted polymer assays

Benito-Pena, E ; Moreno-Bondi, MC ; Aparicio, S ; Orellana, G ; Cederfur, Josefine LU and Kempe, Maria LU (2006) In Analytical Chemistry 78(6). p.2019-2027
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... (More)
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. (Less)
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author
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organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Analytical Chemistry
volume
78
issue
6
pages
2019 - 2027
publisher
The American Chemical Society (ACS)
external identifiers
  • wos:000236307700038
  • scopus:33645325911
ISSN
1520-6882
DOI
10.1021/ac051939b
language
English
LU publication?
yes
id
331d80b4-5735-45b5-af13-7c7871b322f6 (old id 415263)
date added to LUP
2016-04-01 12:11:31
date last changed
2021-06-08 05:32:48
@article{331d80b4-5735-45b5-af13-7c7871b322f6,
  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 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.},
  author       = {Benito-Pena, E and Moreno-Bondi, MC and Aparicio, S and Orellana, G and Cederfur, Josefine and Kempe, Maria},
  issn         = {1520-6882},
  language     = {eng},
  number       = {6},
  pages        = {2019--2027},
  publisher    = {The American Chemical Society (ACS)},
  series       = {Analytical Chemistry},
  title        = {Molecular engineering of fluorescent penicillins for molecularly imprinted polymer assays},
  url          = {http://dx.doi.org/10.1021/ac051939b},
  doi          = {10.1021/ac051939b},
  volume       = {78},
  year         = {2006},
}