Immunochemical Determination of 2,4,6-Trichloroanisole as the Responsible Agent for the Musty Odor in Foods. 1. Molecular Modeling Studies for Antibody Production

详细信息    查看全文

• 作者：Nuria Sanvicens ; Francisco Sá ; nchez-Baeza ; and M.-Pilar Marco
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2003
• 出版时间：July 2, 2003
• 年：2003
• 卷：51
• 期：14
• 页码：3924 - 3931
• 全文大小：150K
• 年卷期：v.51,no.14(July 2, 2003)
• ISSN：1520-5118

文摘

Nine antisera have been raised against 2,4,6-trichloroanisole (2,4,6-TCA) by immunizing them withthree 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 haptenB (5-(2,4,6-trichlorophenoxy)pentanoic acid), the spacer was placed in the molecule substituting themethoxy group. Finally, hapten C (3-(3,5-dichloro-4-methoxyphenyl)propanoic acid) held the spacerarm 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 theintroduction of the linker. The evaluation of the avidity of the resulting antibodies demonstrates thatthe orientation produced by the spacer arm must also be considered an essential aspect. Thescreening for competitive assays performed after synthesizing a battery of heterologous competitorshas provided with these antibodies eight indirect enzyme-linked immunosorbent assays with acceptableproperties. From the number of assays obtained, their maximal absorbance, their signal-to-noiseratio, the slope, and the IC₅₀ values obtained, it can be concluded that hapten C provided the bestantibodies.Keywords: Trichloroanisole; hapten design; molecular modeling; musty odor; wine; cork; immunoassay