Synthesis and bioassay of carbamate inhibitors of the juvenile hormone hydrolyzing esterases from the housefly, Musca domestica

Mumby, Susanne M.; Hammock, Bruce D.; Sparks, Thomas C.; Ota, Kenji

doi:10.1021/jf60224a021

Cited by 9 publications

(3 citation statements)

References 17 publications

(21 reference statements)

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“…Finally, early day 3 (1 day prior to pupation) last instar larvae of the cabbage looper (Trichoplusia ni) were placed in 1-oz plastic pill cups containing 3 mL of a pinto bean based diet (Shorey and Hale, 1965) and treated topically with the test compound in acetone in pyridine. In each case the test insects were held at 24 °C on a 16:8 lightidark cycle and insects which failed to emerge as adults were scored as dead (Mumby et al, 1979). The dosage-mortality data were corrected for the minimal control mortality by using Abbott's formula (Abbott, 1925), and the biological activity of the experimental compound was compared to that of diflubenzuron or BAY SDR 8514 obtained in the same bioassay.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of haptens and potential radioligands and development of antibodies to insect growth regulators diflubenzuron and BAY SIR 8514

Wie¹,

Sylwester²,

Wing³

et al. 1982

J. Agric. Food Chem.

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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 ["C]diflubenzuron, Ouchterlony gel diffusion, and immunoelectrophoresis.

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Section: Methodsmentioning

confidence: 99%

Synthesis of haptens and potential radioligands and development of antibodies to insect growth regulators diflubenzuron and BAY SIR 8514

Wie¹,

Sylwester²,

Wing³

et al. 1982

J. Agric. Food Chem.

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“…comm.). M. domestica JHE exhibits an atypical pattern of sensitivity to a range of organophosphates, carbamates and other esterase inhibitors (Mumby et al, 1979;Sparks and Hammock, 1980) and Cu.lex pipiens pipiens JHE is resistant to several effective inhibitors of other JHEs (Hooper, 1976). Taken together these atypical inhibitor sensitivities suggest structural differences between the active sites of dipteran and non-dipteran JHEs.…”

Section: In Vitro Inhibitors Of Jhementioning

confidence: 98%

Characterisation of juvenile hormone esterase in Drosophila melanogaster

Campbell

Healy

Oakeshott

1992

Insect Biochemistry and Molecular Biology

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Juvenile hormone (JH) is one of the main morphogenic hormones of insects and degradation of the hormone is believed to play an important role in its regulation in many insects. The two main routes for JH degradation are hydroy sis by JH esterase (JHE) and JH epoxide hydrolase (JHEH). • A major focus of research has been on juvenile hormone esterase (JHE) found in the haemolymph of final instar lepidopteran larvae, although considerable hydrolysis of JH occurs in other tissues and at other life stages. In contrast, no comprehensive study of JH degradation has been undertaken in any dipteran species. However, the available evidence suggests that very little JH degrading activity is found in the haemolymph of Diptera and several dipteran JHEs exhibit atypical patterns of sensitivity to inhibitors. These data suggested that both the expression pattern and the biochemical properties of dipteran JH degrading enzymes may differ from other insect orders, and therefore, that the role of JH degradation may be different.The aim of this project was to comprehensively characterise JH degradation in the dipteran, Drosophila melanogaster, with special emphasis on JHE. The first objective was to identify the JH degrading enzymes of D . melanogaster and the second was to deterrnine their expression patterns and biochemical properties in order to determine thei~ role in the regulation of JH titre. These data were compared with other data to deterrnine whether a general model could be developed for dipteran JH titre regulation. Finally, the roles of JH hydrolysis in the regulation of JH titre were compared among Diptera, Lepidoptera and other insects.Two approaches were taken to identify the JH degrading enzymes of D. melanogaster. The first was to investigate the properties of an esterase, denoted EST20, which can be visualised after native polyacrylarnide gel electrophoresis using artificial esterase substrates, a-and B-naphthylacetate. EST20 is shown to be a likely homologue of the p-esterase of Drosophila virilis, which has been claimed to be the JHE of this species. However, this study shows that JH hydrolytic activity is associated with neither EST20 in D. melanogaster nor the p-esterase in D . virilis.The second approach was to use a radiometric assay which identified two JH hydrolysing enzymes, JHE and JHEH. The developmental profile of JH hydrolytic activity in D. melanogaster correlates inversely with profiles of JH titre and production. Key features are prewandering and prepupal maxima of JH hydrolytic activity in whole body homogenates of final instar larvae. This developmental profile of expression is similar to the lepidopteran pattern suggesting that the role of JH hydrolysis is essentially similar during this period. In D. melanogaster, the prewandering maximum consists mainly of JHEH whereas the prepupal peak consists mainly of JHE. However, the relative contributions of JHE and JHEH at these times differs both among the Diptera and in other orders.JHE from the prepupal stage was purified to homogeneity by selectiv...

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“…Considering its activity, an insect juvenile hormone-like activity was proposed (Canela et al, 1999). Although there exist many potential sites for selective disruption of endocrine function in insects (Mumby et al, 1979), it is difficult to find a clear structure-activity relationship (Schvartzapel et al, 1996). However, two hypotheses can be considered when the structure of compound 1a is matched with the juvenile hormone 0 (JH 0) structure.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Phenoxyphenyl Pyridine and Pyrazine Carboxamides. Activity against Cydia pomonella (L.) Eggs

Balcells

Avilla

Profitos

et al. 1999

J. Agric. Food Chem.

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Several N-(4-phenoxyphenyl)pyridinecarboxamides and N-(4-phenoxyphenyl)pyrazinecarboxamides were synthesized from commercially available material, and their ovicidal activities against Cydia pomonella (L.) were tested. Some of the tested products showed a moderate activity when <24-h-old eggs were sprayed using a Potter tower. A significant increase in the length of the development period of the eggs was also observed in many cases. A clear correlation between both effects was noticed: the products that produced higher mortality also produced higher increase of the length of the development. These results seem to confirm our hypothesis that these compounds could be defined as a juvenile hormone analogues.

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Synthesis and bioassay of carbamate inhibitors of the juvenile hormone hydrolyzing esterases from the housefly, Musca domestica

Cited by 9 publications

References 17 publications

Synthesis of haptens and potential radioligands and development of antibodies to insect growth regulators diflubenzuron and BAY SIR 8514

Synthesis of haptens and potential radioligands and development of antibodies to insect growth regulators diflubenzuron and BAY SIR 8514

Characterisation of juvenile hormone esterase in Drosophila melanogaster

Synthesis of Phenoxyphenyl Pyridine and Pyrazine Carboxamides. Activity against Cydia pomonella (L.) Eggs

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