Disease relevance of ALLYLGLYCINE

• Senegalese baboons (Papio papio), with a natural syndrome of photosensitive epilepsy, consistently show generalized myoclonic jerks if stimulated stroboscopically at hourly intervals, two to eight hours after the intravenous administration of allylglycine, 200 mg/kg [1].
• In addition, the unsaturated amino acids allylglycine, homoallylglycine, homopropargylglycine, and 2-butynylalanine all support protein synthesis in E. coli hosts harboring the mutant synthetase [2].
• Bicuculline- and allylglycine-induced epilepsy in developing rats [3].
• Our results suggest that photosensitivity of the lateral geniculate-kindled cat is related to the modification of GABAergic mechanisms, and that when the GL-kindled cat is pretreated with DL-allylglycine it is a reliable model of photosensitive epilepsy [4].
• METHODS: In 7 Senegalese baboons, we examined the effect of unilateral claustral lesioning on generalized convulsive seizures either kindled from the amygdaloid nucleus (AM) and cingulate cortex (CG) or induced by intermittent photic stimulation (IPS) after systemic administration of D,L-allylglycine (AG) [5].

Psychiatry related information on ALLYLGLYCINE

• These alterations are unlikely related to the occurrence of allylglycine-induced convulsions (in 2 of 4 experiments) as electroconvulsive shock did not alter CSF amino acid levels [6].

High impact information on ALLYLGLYCINE

• The design and synthesis of a novel iodine-labile serine protease inhibitor was realized by the use of an ecotin analogue containing allylglycine at position 84 in lieu of methionine [7].
• DL-Allylglycine causes a marked increase in mouse brain ornithine decarboxylase (ODC) activity [8].
• Brain and blood levels of allylglycine in mice following doses sufficient to inhibit glutamate decarboxylase [9].
• A sequence of ruthenium-catalyzed cross metathesis and rhodium-catalyzed hydrogenation of nonproteinaceous allylglycine derivatives has been developed to achieve high-yielding and unambiguous formation of diaminosuberic acid derivatives [10].
• In this study, the stereoisomers of allylglycine were injected into the posterior hypothalamus at a site also shown to be reactive to bicuculline [11].

Chemical compound and disease context of ALLYLGLYCINE

• SC-13504 was given intravenously to baboons with photosensitive epilepsy, Papio papio, with and without prior administration of allylglycine [12].
• Moreover, clonazepam afforded protection against picrotoxin-induced myoclonus in rats pretreated with a submyoclonic GABA reducing dose of allylglycine [13].
• Clonazepam pretreatment inhibited both picrotoxin and allylglycine-induced myoelonus whereas AOAA was effective in inhibiting only picrotoxin-induced myoclonus [13].

Biological context of ALLYLGLYCINE

• Visual evoked potentials (VEPs) from the frontorolandic (FR) cortex and from subcortical nuclei (colliculi superioris, pulvinar, corpori geniculati lateralis, centrum medianum, ventralis lateralis) and from pontine reticular formation were analyzed in Papio papio monkeys rendered photosensitive by a subconvulsant dose of allylglycine [14].
• Metabolism of allylglycine and cis-crotylglycine by Pseudomonas putida (arvilla) mt-2 harboring a TOL plasmid [15].
• Using ion-sensitive microelectrodes, we showed that in the allylglycine-treated photosensitive baboon, prolonged light-induced generalized seizures were accompanied by abnormally large decreases in the concentration of extracellular calcium ions, reaching values at which chemical synaptic transmission was certainly very reduced or blocked [16].
• On GABAergic mechanisms in the optokinetic nystagmus of the frog: effects of bicuculline, allylglycine and SR 95103, a new GABA antagonist [17].
• 1. The response of individually caged mice to the lethal actions of allylglycine and strychnine was evaluated in animals previously conditioned on an LD 12:12 (12 h light-12 h darkness) schedule in a controlled environment [18].

Anatomical context of ALLYLGLYCINE

• Photosensitivity was acquired as a result of kindling in the lateral geniculate body (GL), and the GL-kindled cat pretreated with DL-allylglycine showed a stable level of photosensitivity [19].
• Behavioural effects of allylglycine (2-amino-4-pentenoic acid) and 2-keto-4-pentenoic acid following focal injection into the rat cerebellum and caudate nucleus [proceedings] [20].
• The inhibition by 5-HTP of picrotoxin-induced myoclonic movements was found to correlate well with an increased 5-HT release from the cerebral cortex. p-Chlorophenylalanine (PCPA) pretreatment aggravated the actions of both picrotoxin and allylglycine by shortening their myoclonic latencies [21].
• D-Allylglycine is active only at the brain stem and cerebellum because D-amino acid oxidase is largely confined to these brain areas [22].
• This finding together with the observation that after DL-AG the visual evoked potentials increased in the primary visual cortex and decreased in the centre median nucleus and in the reticular formation support the view about the role of the cortex in the increased brain excitability and in the increased photosensitivity after allylglycine [23].

Associations of ALLYLGLYCINE with other chemical compounds

• The effects of DL-allylglycine, an inhibitor of GABA synthesis, on the responses to photic stimulation were studied in the cat kindled in the lateral geniculate body (GL) [4].
• Progabide was tested in naturally and allylglycine-induced photosensitive baboons (Papio papio) [24].
• The anticonvulsant properties of CL 218,872 against bicuculline and allylglycine-induced seizures were correlated with benzodiazepine receptor occupancy by assessment of electroencephalographic activity during positron emission tomography studies [25].
• The action of the convulsant drugs, methionine sulfoximine (MSO), 3-mercaptopropionate (3-MP), megimide (MG), and allylglycine on the binding of L-[14C]aspartate, L-[14C]glutamate and [14C]GABA to a hydrophobic protein fraction isolated from rat cerebral cortex was studied [26].
• Allylglycine increased the concentration of pyridoxal phosphate in cerebral cortex from 1011.4 +/- 25.0 to 1318.0 +/- 66.3 and decreased it in cerebellum from 1289.0 +/- 49 to 1147.7 +/- 119.4 ng/g wet tissue during the preictal period [27].

Gene context of ALLYLGLYCINE

• Effect of 3-aminopropanesulfonic acid and allylglycine on prolactin release in male rats [28].
• Ring-closing metathesis of C-terminal allylglycine residues with an N-terminal beta-vinyl-substituted phosphotyrosyl mimetic as an approach to novel Grb2 SH2 domain-binding macrocycles [29].
• Thus, although these enzymes could use allylglycine as the acyl donor they could not employ it as the acyl acceptor in peptide synthesis [30].
• Epileptic photosensitivity was acquired as a result of kindling in the lateral geniculate body (GL), and a GL-kindled cat pretreated with DL-allylglycine was found to be a useful model of epilepsy for assessing the efficacy of anticonvulsant drugs [31].
• We have studied the antimyoclonic effect of clonazepam and compared it with that of aminooxyacetic acid (AOAA), a GABA transaminase inhibitor, against myoclonus induced by picrotoxin, a GABA receptor antagonist and allylglycine, a drug which inhibits synthesis and release of GABA [13].

Analytical, diagnostic and therapeutic context of ALLYLGLYCINE

• X-ray crystallography of the proteolytic core of rat mu-calpain inactivated by the epoxide compounds WR gamma-cyano-alpha-aminobutyric acid (S,S) and WR allylglycine (R,R) reveals that the stereochemistry of the epoxide influences positioning and orientation of the P2 residue, facilitating alternate interactions within the S2 pocket [32].
• Cortical and subcortical multiunitary activities (MUA) and EEG were simultaneously recorded in baboons made photosensitive by a subconvulsant dose of DL-allylglycine [33].

References