Hapten synthesis, antibody development, and competitive inhibition enzyme immunoassay for s-triazine herbicides

Marvin H. Goodrow, Robert O. Harrison, Bruce D. Hammock

Research output: Contribution to journalArticle

194 Scopus citations

Abstract

Two families of carboxylic acid derivatives of the herbicides atrazine and simazine were synthesized for use as haptens in the development of immunoassays. One family was made by using monosubstituted (alkylamino)cyanuric chlorides and a variety of ω-amino acids, giving spacers of varying lengths attached to one secondary amino group. The second family resulted from the replacement of the 2-chloro group of atrazine or simazine with 3-mercaptopropanoic acid. These haptens were conjugated to carrier proteins via N-hydroxysuccinimide active esters to make immunogens and ELISA antigens. Mono(alkylamino)cyanuric chlorides were also conjugated directly to bovine serum albumin and thyroglobulin under physiological conditions. ELISA and competitive inhibition ELISA results demonstrated that antibodies from immunized rabbits bound all of the conjugated and free s-triazines tested, including the parent compounds atrazine and simazine. The degree of binding was dependent on the N-alkyl groups present and on the length and position of attachment of the spacer arm. These results illustrate the usefulness of this synthetic approach in easily producing immunogenic haptens for a class of compounds that are difficult to work with because of their low solubility.

Original languageEnglish (US)
Pages (from-to)990-996
Number of pages7
JournalJournal of Agricultural and Food Chemistry
Volume38
Issue number4
StatePublished - 1990

ASJC Scopus subject areas

  • Agricultural and Biological Sciences (miscellaneous)
  • Food Science
  • Chemistry (miscellaneous)

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