New trifluoropropanone sulfides as highly active and selective inhibitors of insect juvenile hormone esterase

A. Székács, Bruce D. Hammock, Yehia A I Abdel-Aal, Premjit P. Halarnkar, Matthew Philpott, György Matolcsy

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

A series of α,α′-bis(2-oxo-3,3,3-trifluoropropylthio)alkanes was synthesized by the alkylation of the appropriate α,α′-alkanedithiol with 3-bromo-1,1,1-trifluoropropan-2-one. The compounds were tested for in vitro inhibition of insect juvenile hormone esterase (JHE), electric eel acetylcholinesterase (AChE), porcine carboxylesterase, and yeast lipase. Inhibition of hemolymph JHE from fifth instar larvae of the cabbage looper, Trichoplusia ni (Hübner) (Lepidotera: Noctuidae), was in the nanomolar range for many compounds. The inhibition of the other three enzymes was only moderate in comparison to JHE. The inhibition of JHE was compared to carbon chain length, differing heteroatoms, and presence of methyl side-chains. The most effective compound was 1,1,1,16,16,16-hexafluoro-4,13-dithiahexadecane-2,15-dione (I50: 8.2 × 10-10 M). The kinetics of inhibition were found to be time-dependent against both JHE and AChE enzymes using representative compounds of both high and low inhibitory potential. Second-order inhibition velocity constants were determined and found to be in agreement with the I50 values.

Original languageEnglish
Pages (from-to)112-124
Number of pages13
JournalPesticide Biochemistry and Physiology
Volume33
Issue number2
DOIs
Publication statusPublished - 1989

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Insect Hormones
juvenile hormone esterase
insect hormones
Sulfides
sulfides
Trichoplusia ni
Acetylcholinesterase
acetylcholinesterase
Electrophorus
alkylation
carboxylesterase
Carboxylesterase
Alkanes
Hemolymph
Brassica
Alkylation
Enzymes
enzymes
Lipase
Chain length

ASJC Scopus subject areas

  • Agronomy and Crop Science
  • Biochemistry
  • Physiology

Cite this

New trifluoropropanone sulfides as highly active and selective inhibitors of insect juvenile hormone esterase. / Székács, A.; Hammock, Bruce D.; Abdel-Aal, Yehia A I; Halarnkar, Premjit P.; Philpott, Matthew; Matolcsy, György.

In: Pesticide Biochemistry and Physiology, Vol. 33, No. 2, 1989, p. 112-124.

Research output: Contribution to journalArticle

Székács, A. ; Hammock, Bruce D. ; Abdel-Aal, Yehia A I ; Halarnkar, Premjit P. ; Philpott, Matthew ; Matolcsy, György. / New trifluoropropanone sulfides as highly active and selective inhibitors of insect juvenile hormone esterase. In: Pesticide Biochemistry and Physiology. 1989 ; Vol. 33, No. 2. pp. 112-124.
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