Toxic Factor from ‘Agenized’ Proteins: Methionine as the Essential Reactant

Bentley, H. R.; McDermott, E. E.; Pace, J.; Whitehead, J. K.; Moran, T. F.

doi:10.1038/165150a0

Cited by 69 publications

(65 citation statements)

References 5 publications

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“…MSO has been described as the chemical responsible for seizures induced in various animals after consumption of agenized flour, during the mid-1950s [157-159]; and it was therefore used to induce seizures in different animals, essentially rats and mice with characterized EEG alterations before and during seizures [124, 154, 160, 161]. Moreover, some plants of the Cnestis genus, from Madagascar and Asia, were used to kill running dogs by causing severe convulsions.…”

Section: Mso-induced Epilepsymentioning

confidence: 99%

Epilepsy, Regulation of Brain Energy Metabolism and Neurotransmission

Cloix

Hevor

2009

CMC

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Seizures are the result of a sudden and temporary synchronization of neuronal activity, the reason for which is not clearly understood. Astrocytes participate in the control of neurotransmitter storage and neurotransmission efficacy. They provide fuel to neurons, which need a high level of energy to sustain normal and pathological neuronal activities, such as during epilepsy. Various genetic or induced animal models have been developed and used to study epileptogenic mechanisms. Methionine sulfoximine induces both seizures and the accumulation of brain glycogen, which might be considered as a putative energy store to neurons in various animals. Animals subjected to methionine sulfoximine develop seizures similar to the most striking form of human epilepsy, with a long pre-convulsive period of several hours, a long convulsive period during up to 48 hours and a post convulsive period during which they recover normal behavior. The accumulation of brain glycogen has been demonstrated in both the cortex and cerebellum as early as the pre-convulsive period, indicating that this accumulation is not a consequence of seizures. The accumulation results from an activation of gluconeogenesis specifically localized to astrocytes, both in vivo and in vitro. Both seizures and brain glycogen accumulation vary when using different inbred strains of mice. C57BL/6J is the most “resistant” strain to methionine sulfoximine, while CBA/J is the most “sensitive” one. The present review describes the data obtained on methionine sulfoximine dependent seizures and brain glycogen in the light of neurotransmission, highlighting the relevance of brain glycogen content in epilepsies.

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Section: Mso-induced Epilepsymentioning

confidence: 99%

Epilepsy, Regulation of Brain Energy Metabolism and Neurotransmission

Cloix

Hevor

2009

CMC

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“…42 and 100 mg (0.276 mmol, 1.0 equiv.) Cu(OTf) 2 were stirred for 30 min under vacuum. Then under an atmosphere of dry argon 0.7 mL dry dichloromethane were added via syringe.…”

Section: Cu Complex 52mentioning

confidence: 99%

Geminal Bis(sulfoximine)s: Synthesis and Applications in Asymmetric Catalysis

2004

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A number of C 2 -symmetrical geminal bis-(sulfoximine)s have been prepared for the first time and used as ligands in boron-mediated reductions of acetophenone and copper complex-catalyzed 1,4-additions of diethylzinc to 2-cyclohexenone. The copper complex of bis(sulfoximine) 46 was found to be highly active in this type of reaction, furnishing the addition product in nearly quantitative yield even at À 90 8C. From the reaction of bis(sulfoximine) 42 with Cu(OTf) 2 a copper complex was isolated and characterized by X-ray structural analysis. A mixture of SES-Cl and NaN 3 in acetonitrile was found to behave like SES-N 3 in FeCl 2 -mediated iminations of sulfoxides, affording the corresponding sulfoximines with complete retention of the sulfur configuration.

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“…On the other hand, sulfoximines were discovered by Bentley in 1950 [3] and are considered as the nitrogen analogues of sulfones. They share some of their properties such as the acidic α-hydrogen but the nitrogen atom provides an additional place for structural modifications by nucleophilic reactions [4].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Bioactivity of New Phosphorylated R,R’-substituted Sulfoximines

Reinhard

Licastro

2005

Molecules

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R,R’-disubstituted sulfoximines were phosphorylated with O,O–diethylchloro phosphate and phosphorothionate to obtain new organophosphorus compounds. After purification they were characterized by GC-MS and 1H-NMR. The toxicity of the synthesized O,O-diethyl N-(R,R’-disubstituted sulfoximine) phosphoro-amidothionates was assayed on Musca domestica. It was found that the methyl phenyl derivative was the most toxic compound, followed by the dipropyl and dibutyl derivatives. The dihexyl compound was the less toxic of all the assayed compounds, being one hundred times less toxic than a paraoxon standard The anticholinesterasic activity of the corresponding phosphoramidates was assayed on homogenates of house flies’ heads, giving values similar to paraoxon for the methyl phenyl derivative.

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Toxic Factor from ‘Agenized’ Proteins: Methionine as the Essential Reactant

Cited by 69 publications

References 5 publications

Epilepsy, Regulation of Brain Energy Metabolism and Neurotransmission

Epilepsy, Regulation of Brain Energy Metabolism and Neurotransmission

Geminal Bis(sulfoximine)s: Synthesis and Applications in Asymmetric Catalysis

Synthesis and Bioactivity of New Phosphorylated R,R’-substituted Sulfoximines

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