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Immunochemical determination of 2,4,6-trichloroanisole as the responsible agent for the musty odor in foods. 1. Molecular modeling studies for antibody production

AutorSanvicens, Nuria; Sánchez Baeza, Francisco J.; Marco, María Pilar
Palabras claveTrichloroanisole
Hapten design
Molecular modeling
Musty odor
Fecha de publicación3-jun-2003
EditorAmerican Chemical Society
CitaciónJournal of Agricultural and Food Chemistry 51(14): 3924–3931 (2003)
ResumenNine antisera have been raised against 2,4,6-trichloroanisole (2,4,6-TCA) by immunizing them with three different haptens. With the spacer arm at the meta position, hapten A (3-(2,4,6-trichloro-3-methoxyphenyl)propanoic acid) preserved all of the functional groups of the target analyte. In hapten B (5-(2,4,6-trichlorophenoxy)pentanoic acid), the spacer was placed in the molecule substituting the methoxy group. Finally, hapten C (3-(3,5-dichloro-4-methoxyphenyl)propanoic acid) held the spacer arm at the para position instead of the chlorine atom of the target analyte. Using theoretical models, we have studied how the molecular geometry and the electronic distribution are affected by the introduction of the linker. The evaluation of the avidity of the resulting antibodies demonstrates that the orientation produced by the spacer arm must also be considered an essential aspect. The screening for competitive assays performed after synthesizing a battery of heterologous competitors has provided with these antibodies eight indirect enzyme-linked immunosorbent assays with acceptable properties. From the number of assays obtained, their maximal absorbance, their signal-to-noise ratio, the slope, and the IC50 values obtained, it can be concluded that hapten C provided the best antibodies.
Descripción8 pages, 4 figures, 2 tables.-- PMID: 12822925 [PubMed].-- Printed version published Jul 2, 2003.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jf034003h
Versión del editorhttp://dx.doi.org/10.1021/jf034003h
ISSN0021-8561 (Print)
1520-5118 (Online)
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