Abstract
A variety of synthetic approaches were undertaken, leading to potential haptens and radioligands for the benzoylphenylurea insect growth regulators diflubenzuron and BAY SIR 8514. One successful approach involved derivatization of the aniline nitrogen by ethyl 4-bromobutyrate followed by reaction with an appropriate isocyanate and cleavage of the ethyl ester to yield a free carboxypropyl "handle". Useful haptens were also synthesized by using a 3′-phenolic metabolite of diflubenzuron as well as acetate and amine functionalities in the 4′ position while the N-sulfenyl bond proved too unstable for use as an antigen. With the exception of the sulfenylated derivatives, the haptens lacked significant biological activity on three insect species. Following protein coupling by the active ester or water-soluble diimide method, antibodies were raised to two diflubenzuron haptens in each of seven rabbits immunized as demonstrated by radioimmunoassay using [14C]diflubenzuron, Ouchterlony gel diffusion, and immunoelectrophoresis.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 943-948 |
| Number of pages | 6 |
| Journal | Journal of Agricultural and Food Chemistry |
| Volume | 30 |
| Issue number | 5 |
| State | Published - 1982 |
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ASJC Scopus subject areas
- Agricultural and Biological Sciences (miscellaneous)
- Food Science
- Chemistry (miscellaneous)
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Synthesis of haptens and potential radioligands and development of antibodies to insect growth regulators diflubenzuron and BAY SIR 8514. / Wie, Siong I.; Sylwester, Alan P.; Wing, Keith D.; Hammock, Bruce D.
In: Journal of Agricultural and Food Chemistry, Vol. 30, No. 5, 1982, p. 943-948.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis of haptens and potential radioligands and development of antibodies to insect growth regulators diflubenzuron and BAY SIR 8514
AU - Wie, Siong I.
AU - Sylwester, Alan P.
AU - Wing, Keith D.
AU - Hammock, Bruce D.
PY - 1982
Y1 - 1982
N2 - A variety of synthetic approaches were undertaken, leading to potential haptens and radioligands for the benzoylphenylurea insect growth regulators diflubenzuron and BAY SIR 8514. One successful approach involved derivatization of the aniline nitrogen by ethyl 4-bromobutyrate followed by reaction with an appropriate isocyanate and cleavage of the ethyl ester to yield a free carboxypropyl "handle". Useful haptens were also synthesized by using a 3′-phenolic metabolite of diflubenzuron as well as acetate and amine functionalities in the 4′ position while the N-sulfenyl bond proved too unstable for use as an antigen. With the exception of the sulfenylated derivatives, the haptens lacked significant biological activity on three insect species. Following protein coupling by the active ester or water-soluble diimide method, antibodies were raised to two diflubenzuron haptens in each of seven rabbits immunized as demonstrated by radioimmunoassay using [14C]diflubenzuron, Ouchterlony gel diffusion, and immunoelectrophoresis.
AB - A variety of synthetic approaches were undertaken, leading to potential haptens and radioligands for the benzoylphenylurea insect growth regulators diflubenzuron and BAY SIR 8514. One successful approach involved derivatization of the aniline nitrogen by ethyl 4-bromobutyrate followed by reaction with an appropriate isocyanate and cleavage of the ethyl ester to yield a free carboxypropyl "handle". Useful haptens were also synthesized by using a 3′-phenolic metabolite of diflubenzuron as well as acetate and amine functionalities in the 4′ position while the N-sulfenyl bond proved too unstable for use as an antigen. With the exception of the sulfenylated derivatives, the haptens lacked significant biological activity on three insect species. Following protein coupling by the active ester or water-soluble diimide method, antibodies were raised to two diflubenzuron haptens in each of seven rabbits immunized as demonstrated by radioimmunoassay using [14C]diflubenzuron, Ouchterlony gel diffusion, and immunoelectrophoresis.
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UR - http://www.scopus.com/inward/citedby.url?scp=0347303432&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0347303432
VL - 30
SP - 943
EP - 948
JO - Journal of Agricultural and Food Chemistry
JF - Journal of Agricultural and Food Chemistry
SN - 0021-8561
IS - 5
ER -