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  • 1
    Electronic Resource
    Electronic Resource
    1-Piperideine as an In Vivo Precursor of the γ-Aminobutyric Acid Homologue 5-Aminopentanoic Acid (1985)
    Oxford, UK : Blackwell Publishing Ltd
    Journal of neurochemistry 45 (1985), S. 0 
    Details
    ISSN: 1471-4159
    Source: Blackwell Publishing Journal Backfiles 1879-2005
    Topics: Medicine
    Notes: Abstract: Intraperitoneal injection of the cyclic imine I-piperideine in mice resulted in measurable quantities of 5-aminopentanoic acid in brain. 5-Aminopentanoic acid is a methylene homologue of γ-aminobutyric acid (GABA) that is a weak GABA agonist. 5-Aminopentanoic acid formed in the periphery was ruled out as the source of brain 5-aminopentanoic acid based on the absence of detection in brain following injection of 100 mg/kg of 5-aminopentanoic acid. Deuterium-labeled I-piperideine was prepared by exchange in deuterated phosphate buffer. Injection of [3,3-2H2] 1-piperideine yielded [2,2-2H2]5-aminopentanoic acid in brain. The results are consistent with uptake of 1-piperideine into brain and oxidation of the precursor to 5-aminopentanoic acid. Inhibition of GABA catabolism by pretreatment with aminooxyacetic acid increased brain concentrations of 5-aminopentanoic acid formed from 1-piperideine, suggesting that 5-aminopentanoic acid is an in vivo substrate of 4-aminobutyrate:2-oxoglutarate aminotransferase.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1111/j.1471-4159.1985.tb04085.x
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  • 2
    Electronic Resource
    Electronic Resource
    Pyrrolines as Prodrugs of γ-Aminobutyric Acid Analogues (1982)
    Oxford, UK : Blackwell Publishing Ltd
    Journal of neurochemistry 38 (1982), S. 0 
    Details
    ISSN: 1471-4159
    Source: Blackwell Publishing Journal Backfiles 1879-2005
    Topics: Medicine
    Notes: Abstract: Δ′-Pyrroline, S-methyl-Δ′-pyrroline, and 5.5-dimethyl-Δ′-pyrroline have been identified as substances metabolized to γ-aminobutyric acid (GABA), 4-aminopentanoic acid (raethyl GABA), and 4-amino-4-methylpen-tanoic acid (dimethyl GABA), respectively. An enzyme system residing in the soluble fraction of rabbit liver catalyzes the conversion of Δ′-pyrroline to GABA and its lactam, 2-pyrrolidinone. Acetaldehyde, allopurinol, and cyanide inhibited the reaction. Incubation of deuterium-labeled Δ′-pyrroline with mouse brain homogenates produced deuterated GABA. Mouse liver 10,000 g supernatant and mouse brain homogenates converted S-methyl-Δ′-pyrroline to methyl GABA, and 5,5-dimethyl-Δ′-pyrroline to dimethyl GABA. Four hours after intraperitoneal injection of 5-methyl-Δ′-pyrroline (200 mg/kg), methyl GABA was detected in mouse brain (0.27 μ-mol/g). Dimethyl GABA (1.21 μmol/g) was determined in mouse brain 30 min after intraperitoneal administration of 5.5-dimethyl-Δ′-pyrroline (200 mg/kg). Neither methyl GABA nor dimethyl GABA penetrated into the central nervous system when administered in the periphery. The present studies suggest that pyrrolines may represent a chemical class of brain-penetrating precursors of pharmacologically active analogues of GABA.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1111/j.1471-4159.1982.tb05348.x
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  • 3
    Electronic Resource
    Electronic Resource
    Biosynthesis of 5-Aminopentanoic Acid and 2-Piperidone from Cadaverine and 1-Piperideine in Mouse (1984)
    Oxford, UK : Blackwell Publishing Ltd
    Journal of neurochemistry 43 (1984), S. 0 
    Details
    ISSN: 1471-4159
    Source: Blackwell Publishing Journal Backfiles 1879-2005
    Topics: Medicine
    Notes: 1-Piperideine, 5-aminopentanoic acid, and its lactam, 2-piperidone, were identified as metabolites of cadaverine in 10,000 g mouse liver supernatants to which diamine oxidase had been added. Both metabolites were also found when the cadaverine metabolite 1-piperideine was incubated with the preparation which suggested that 1-piperideine is an intermediate in the formation of 5-ammopentanoic acid and 2-piperidone. Identification of the metabolites was based on gas chromatography-mass spectrometric analysis in comparison to authentic standards. Mouse brain homogenates converted 1-piperideine to 5-aminopentanoic acid. The results suggest that the metabolic fate of cadaverine may provide precursors of pharmacologically active analogues of GABA.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1111/j.1471-4159.1984.tb06088.x
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  • 4
    Electronic Resource
    Electronic Resource
    Applications of deuterium labeling in the study of the in vitro conversion of Δ1-pyrroline to 4-aminobutanoic acid and 2-pyrrolidinone (1980)
    Chichester : Wiley-Blackwell
    Biological Mass Spectrometry 7 (1980), S. 525-528 
    Details
    ISSN: 1052-9306
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Δ1-Pyrroline is a putrescine metabolite that is biotransformed by rabbit liver preparations to 4-aminobutanoic acid and its lactam, 2-pyrrolidinone. Analysis of dilute aqueous solutions of Δ1-pyrroline by proton nuclear magnetic resonance indicated that the predominating species in the liver incubation preparations was Δ1-pyrroline monomer, although other species, such as 4-aminobutyraldehyde and Δ1-pyrroline trimer, may exist in equilibrium with the monomer. [2H12]-Δ1-Pyrroline trimer was synthesized from [2H5]pyrrolidine by conversion to the N-chloro derivative followed by dehydrohalogenation. 4-Aminobutanoic acid was measured by a gas chromatographic mass spectrometric assay after derivatization with dimethylformamide dimethyl acetal. The 4-aminobutanoic acid homologue, 5-aminovaleric acid, served as internal standard. 2-Pyrrolidinone was hydrolyzed and measured as 4-aminobutanoic acid. A comparison of the amounts of product formed following incubation of labeled and unlabeled Δ1-pyrroline indicated a significant isotope effect in the formation of 2-pyrrolidinone. The influence of the label was much less on 4-aminobutanoic acid production. The results suggest that there are two separate pathways involved in the reaction.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/bms.1200071114
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  • 5
    Electronic Resource
    Electronic Resource
    Detection of the in vivo conversion of 2-pyrrolidinone to γ-aminobutyric acid in mouse brain† GABA = γ-aminobutyric acid; AVA = 5-aminovaleric acid; DMF-DMA = N,N-dimethylformamide dimethyl acetal (1979)
    Chichester : Wiley-Blackwell
    Biological Mass Spectrometry 6 (1979), S. 23-26 
    Details
    ISSN: 0306-042X
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Labeled γ-aminobutyric acid was detected in mouse brain following intravenous injections of deuterium labeled 2-pyrrolidinone. [2H6]Pyrrolidinone was prepared by the reduction of [2H4]succinimide with lithium aluminum deuteride. Quantification was accomplished by a gas chromatography mass spectrometry assay method. γ-Aminobutyric acid and internal standard, 5-aminovaleric acid, were converted to volatile derivatives by treatment with N,N-dimethylformamide dimethyl acetal. Quantitative estimates were derived from peak area measurements obtained from monitoring the parent ions of the γ-aminobutyric acid and internal standard derivatives by repetitive scanning during the GC run. The conversion of pyrrolidinone to γ-aminobutyric acid may provide a method for labeling central γ-aminobutyric acid pools.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/bms.1200060106
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