Inhibition of insect juvenile hormone epoxide hydrolase: asymmetric synthesis and assay of glycidol-ester and epoxy-ester inhibitors of Trichoplusia ni epoxide hydrolase

Linderman, Russell J.; Roe, R. Michael; Harris, Shannon V.; Thompson, Deborah

doi:10.1016/s0965-1748(00)00048-5

Cited by 11 publications

(4 citation statements)

References 44 publications

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“…For example, by placing the glycidol functionality in a simple methyl ester where it corresponded to the 10,11 position of JH, a potent inhibitor of the JHEH of T. ni was produced. Similarly, by making a simple epoxy ester in much the same way as earlier work by Hafferl and Gilbert (unpublished), a good competitive substrate was synthesized 50. A rapid screen using definitive JHEH is, of course, an important tool for developing JHEH inhibitors.…”

Section: Insect Epoxide Hydrolasesmentioning

confidence: 94%

Gerry Brooks and epoxide hydrolases: four decades to a pharmaceutical

Morisseau

Hammock

2008

Pest Management Science

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The pioneering work of Gerry Brooks on cyclodiene insecticides led to the discovery of a class of enzymes known as epoxide hydrolases. The results from four decades of work confirm Brooks' first observations that the microsomal epoxide hydrolase is important in foreign compound metabolism. Brooks and associates went on to be the first to carry out a systematic study of the inhibition of this enzyme. A second role for this enzyme family was in the degradation of insect juvenile hormone (JH). JH epoxide hydrolases have now been cloned and expressed from several species, and there is interest in developing inhibitors for them. Interestingly, the distantly related mammalian soluble epoxide hydrolase has emerged as a promising pharmacological target for treating hypertension, inflammatory disease and pain. Tight-binding transition-state inhibitors were developed with good ADME (absorption, distribution, metabolism and excretion). These compounds stabilize endogenous epoxides of fatty acids, including arachidonic acid, which have profound therapeutic effects. Now EHs from microorganisms and plants are used in green chemistry. From his seminal work, Dr Brooks opened the field of epoxide hydrolase research in many directions including xenobiotic metabolism, insect physiology and human health, as well as asymmetric organic synthesis. 

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Section: Insect Epoxide Hydrolasesmentioning

confidence: 94%

Gerry Brooks and epoxide hydrolases: four decades to a pharmaceutical

Morisseau

Hammock

2008

Pest Management Science

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“…Glycidol-ester and epoxy-ester analogs of methyl 10,11-epoxy-11-methyldodecanoate (MEMD) are potent inhibitors of the JHEH, but they may not be specific to insects. 97) Recently, amide-, urea-and carbamate-type analogs have been reported as potential EH inhibitors in mammals, 98,99) and some potent analogs inhibited JHEH activity in vitro. 100) Interestingly, most of the inhibitors of the mammalian EHs are not effective on insect JHEH, 100) but converse studies of inhibitors for JHEH that do not act on the mammalian enzyme have not been reported.…”

Section: Inhibitors Of Metabolic Enzymesmentioning

confidence: 99%

Insect juvenile hormone action as a potential target of pest management

Minakuchi

Riddiford

2006

J. Pestic. Sci.

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Juvenile hormone (JH) is a sesquiterpenoid hormone that regulates growth and development in insects. Since JH is a hormone specific to insects and other arthropods, compounds disrupting JH action in insects are expected to be ideal insecticides with low toxicity to non-target organisms. Many natural or synthetic analogs with JH-like or anti-JH activity have been identified, and some potent JH mimics have been used as insecticides. Recent studies on the enzymes in JH biosynthetic and metabolic pathways should be helpful for the discovery of more potent analogs and for the establishment of new means of pest management using recombinant DNA technology. © Pesticide Science Society of Japan Keywords: juvenile hormone (JH), insect metamorphosis, insect growth regulators, biosynthesis and metabolism of JH. Review* To whom correspondence should be addressed. E-mail: chieka_minakuchi@yahoo.com © Pesticide Science Society of Japan doptera. 17,18) Higher Diptera such as D. melanogaster and the blowfly Calliphora vomitoria produce JH III bisepoxide. 19,20) A small amount of methyl farnesoate, a precursor of JH III, was found in cockroach embryos and larvae. [20][21][22] Methyl farnesoate has also been identified in crustaceans 23) and is thought to have a JH-like action in female reproduction. 24)12Ј-OH JH III identified from the corpora allata of the African locust Locusta migratoria migratorioides was reported to exhibit JH activity when a high dose of this compound was topically applied to Tenebrio pupae. 25,26) Biosynthesis, Transport and Metabolism of Juvenile HormoneIn insects, JH is synthesized in the corpora allata via the mevalonate pathway (Fig. 2).27) The mevalonate pathway also exists in mammals and plants, and the early steps from acetylCoA to farnesyl diphosphate are conserved among these organisms. Importantly, insects and other arthropods do not synthesize cholesterol de novo but have to acquire it from dietary sources because they lack the genes encoding squalene synthase and other subsequent enzymes of the sterol branch. 28,29) Another peculiarity of the mevalonate pathway in insects is the capacity to synthesize JH via the isoprenoid branch.The genes encoding the enzymes in the mevalonate pathway from acetyl-CoA to farnesyl diphosphate have been identified in the genome of D. melanogaster and the malaria mosquito Anopheles gambiae, and in an EST library of the pine engraver Ips pini.27) However, it has been difficult to identify the genes encoding enzymes from farnesyl diphosphate to JH

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“…This activity was originally reported in mammalian cells more than 40 years ago (Jerina et al, 1968 ; Brooks et al, 1970 ). Since then, EHs have been found in a wide range of different organisms including bacteria and fungi (Arand et al, 1999 ; Kotik et al, 2007 ; Liu et al, 2007 ), plants and insects (Kiyosue et al, 1994 ; Stapleton et al, 1994 ; Guo et al, 1998 ; Linderman et al, 2000 ; Morisseau et al, 2000 ). The physiological roles of EHs have been widely studied.…”

Section: Introductionmentioning

confidence: 99%

“…The physiological roles of EHs have been widely studied. These enzymes have been shown to be involved in the detoxification of xenobiotics in mammals (Oesch, 1973 ; Morisseau and Hammock, 2005 ) and fungi (Sutherland, 1992 ), in the general defense system against pathogens and stress response in plants (Kiyosue et al, 1994 ; Guo et al, 1998 ) and in hormone biosynthesis in insects (Linderman et al, 2000 ).…”

Section: Introductionmentioning

confidence: 99%

New Thermophilic α/β Class Epoxide Hydrolases Found in Metagenomes From Hot Environments

Ferrandi

Sayer

Rose

et al. 2018

Front. Bioeng. Biotechnol.

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Two novel epoxide hydrolases (EHs), Sibe-EH and CH65-EH, were identified in the metagenomes of samples collected in hot springs in Russia and China, respectively. The two α/β hydrolase superfamily fold enzymes were cloned, over-expressed in Escherichia coli, purified and characterized. The new EHs were active toward a broad range of substrates, and in particular, Sibe-EH was excellent in the desymmetrization of cis-2,3-epoxybutane producing the (2R,3R)-diol product with ee exceeding 99%. Interestingly these enzymes also hydrolyse (4R)-limonene-1,2-epoxide with Sibe-EH being specific for the trans isomer. The Sibe-EH is a monomer in solution whereas the CH65-EH is a dimer. Both enzymes showed high melting temperatures with the CH65-EH being the highest at 85°C retaining 80% of its initial activity after 3 h thermal treatment at 70°C making it the most thermal tolerant wild type epoxide hydrolase described. The Sibe-EH and CH65-EH have been crystallized and their structures determined to high resolution, 1.6 and 1.4 Å, respectively. The CH65-EH enzyme forms a dimer via its cap domains with different relative orientation of the monomers compared to previously described EHs. The entrance to the active site cavity is located in a different position in CH65-EH and Sibe-EH in relation to other known bacterial and mammalian EHs.

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Inhibition of insect juvenile hormone epoxide hydrolase: asymmetric synthesis and assay of glycidol-ester and epoxy-ester inhibitors of Trichoplusia ni epoxide hydrolase

Cited by 11 publications

References 44 publications

Gerry Brooks and epoxide hydrolases: four decades to a pharmaceutical

Gerry Brooks and epoxide hydrolases: four decades to a pharmaceutical

Insect juvenile hormone action as a potential target of pest management

New Thermophilic α/β Class Epoxide Hydrolases Found in Metagenomes From Hot Environments

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