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Chemical Compound Review

Gabaculin     5-aminocyclohexa-1,3-diene-1- carboxylic acid

Synonyms: DL-Gabaculine, AG-K-81243, SureCN2024044, CCG-204102, NSC-329502, ...
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Disease relevance of DL-Gabaculine

  • A gabaculine-tolerant Synechococcus strain, GR6, was found to produce a GSA-AT less sensitive to the inhibitor [1].
  • Studies on the kinetics and stoichiometry of inactivation of Pseudomonas omega-amino acid:pyruvate transaminase by gabaculine [2].
  • Inhibition of haem synthesis in the transformed E. coli cells expressing cytochrome b5, by the use of gabaculin or succinylacetone, prevented the assembly of the cytochrome b5 holoprotein but had little effect on the accumulation of cytochrome apoprotein [3].
  • Gabaculine (5-amino-1,3-cyclohexadienylcarboxylic acid, 1), a naturally occurring neurotoxin isolated from Streptomyces toyocaenis, has been shown to be a mechanism-based inactivator of gamma-aminobutyric acid aminotransferase (GABA-AT) (Rando, R. R. Biochemistry 1977, 16, 4604) [4].
  • The effect of the tetrapyrrole biosynthesis inhibitor gabaculine on the expression of specific genes involved in phycocyanin biosynthesis was investigated in cultures of Synechococcus PCC6301 in nitrogen chlorosis, and during recovery to nitrogen sufficiency [5].

High impact information on DL-Gabaculine


Chemical compound and disease context of DL-Gabaculine

  • However, in Synechococcus 6301 strain GR6, a cyanobacterium that is resistant to 100 microM gabaculine, this enzyme has undergone two changes in structure: a deletion of three amino acids from positions 5 to 7 and the substitution of isoleucine for methionine at position 248 [11].

Biological context of DL-Gabaculine

  • However, inhibition was overcome after an extended lag period, following which cell growth proceeded at a similar rate to that of control cells not exposed to gabaculine [12].
  • We also observed a decrease in the global energetic creatine-phosphocreatine pool, which also could be related to the sedative properties of gabaculine, measurable by the diminution of cortical electrical activity and mean arterial blood pressure [13].
  • The results suggest that gabaculine-induced sniffing and head movement were mediated by nigral GABAergic synapses and were independent of any dopaminergic system, and that the high ambulation at 24 h after operation may have been due to a non-specific effect of abnormal GABA elevation in thalamus and/or nigra [14].
  • Gabaculine (250 muM), a GABA transaminase inhibitor, suppressed OMP-induced oxygen consumption but not L-leucine- or glucose-stimulated respiration [15].

Anatomical context of DL-Gabaculine


Associations of DL-Gabaculine with other chemical compounds


Gene context of DL-Gabaculine

  • However, when the GTR was expressed in the presence of 3-amino-2,3- dihydrobenzoic acid (gabaculine), an inhibitor of heme synthesis, the purified GTR had 60 to 70% less bound heme than control GTR, and it was inhibited by hemin in vitro [26].
  • Growth and chlorophyll accumulation in equivalent strains with the hemL gene containing either the deletion or the transition characteristic of Synechococcus 6301 GR6 were inhibited by 10 microM gabaculine [11].
  • Intrastriatal injections of 100 micrograms gabaculine induced a rapid and complete inhibition of GABA-T [27].
  • A glutamate-1-semialdehyde aminotransferase, the terminal enzyme in the conversion of glutamate to ALA in chloroplasts, was detected in 6803 cell extracts by the conversion of glutamate-1-semialdehyde to ALA and by the inhibition of this reaction by gabaculin [28].
  • In cells depleted of tetrapyrrole pathway intermediates by gabaculine treatment, cytochrome f synthesis was significantly reduced [29].

Analytical, diagnostic and therapeutic context of DL-Gabaculine


  1. Gabaculine-resistant glutamate 1-semialdehyde aminotransferase of Synechococcus. Deletion of a tripeptide close to the NH2 terminus and internal amino acid substitution. Grimm, B., Smith, A.J., Kannangara, C.G., Smith, M. J. Biol. Chem. (1991) [Pubmed]
  2. Studies on the kinetics and stoichiometry of inactivation of Pseudomonas omega-amino acid:pyruvate transaminase by gabaculine. Burnett, G., Yonaha, K., Toyama, S., Soda, K., Walsh, C. J. Biol. Chem. (1980) [Pubmed]
  3. Expression of a biologically active plant cytochrome b5 in Escherichia coli. Smith, M.A., Napier, J.A., Stymne, S., Tatham, A.S., Shewry, P.R., Stobart, A.K. Biochem. J. (1994) [Pubmed]
  4. Isolation and characterization of the product of inactivation of gamma-aminobutyric acid aminotransferase by gabaculine. Fu, M., Silverman, R.B. Bioorg. Med. Chem. (1999) [Pubmed]
  5. Expression of genes involved in phycocyanin biosynthesis following recovery of Synechococcus PCC 6301 from nitrogen starvation, and the effect of gabaculine on cpcBa transcript levels. Gilbert, S.M., Allison, G.G., Rogers, L.J., Smith, A.J. FEMS Microbiol. Lett. (1996) [Pubmed]
  6. Crystal structure of glutamate-1-semialdehyde aminomutase: an alpha2-dimeric vitamin B6-dependent enzyme with asymmetry in structure and active site reactivity. Hennig, M., Grimm, B., Contestabile, R., John, R.A., Jansonius, J.N. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  7. Role of heme in the biosynthesis of cytochrome c6. Howe, G., Merchant, S. J. Biol. Chem. (1994) [Pubmed]
  8. Enzyme-activated irreversible inhibitors of L-ornithine:2-oxoacid aminotransferase. Demonstration of mechanistic features of the inhibition of ornithine aminotransferase by 4-aminohex-5-ynoic acid and gabaculine and correlation with in vivo activity. Jung, M.J., Seiler, N. J. Biol. Chem. (1978) [Pubmed]
  9. Crystal structure of 3-amino-5-hydroxybenzoic acid (AHBA) synthase. Eads, J.C., Beeby, M., Scapin, G., Yu, T.W., Floss, H.G. Biochemistry (1999) [Pubmed]
  10. Glutamate-1-semialdehyde aminotransferase from Sulfolobus solfataricus. Palmieri, G., Di Palo, M., Scaloni, A., Orru, S., Marino, G., Sannia, G. Biochem. J. (1996) [Pubmed]
  11. A suicide vector for allelic recombination involving the gene for glutamate 1-semialdehyde aminotransferase in the cyanobacterium Synechococcus PCC 7942. Allison, G., Gough, K., Rogers, L., Smith, A. Mol. Gen. Genet. (1997) [Pubmed]
  12. The effect of gabaculine on tetrapyrrole biosynthesis and heterotrophic growth in Cyanidium caldarium. Houghton, J.D., Turner, L., Brown, S.B. Biochem. J. (1988) [Pubmed]
  13. Effects of GABA-transaminase inhibition on brain metabolism and amino-acid compartmentation: an in vivo study by 2D 1H-NMR spectroscopy coupled with microdialysis. Piérard, C., Pérès, M., Satabin, P., Guezennec, C.Y., Lagarde, D. Experimental brain research. Experimentelle Hirnforschung. Expérimentation cérébrale. (1999) [Pubmed]
  14. The effects of elevating gamma-amino butyrate content in the substantia nigra on the behaviour of rats. Matsui, Y., Kamioka, T. Eur. J. Pharmacol. (1978) [Pubmed]
  15. Oxo-4-methylpentanoic acid directs the metabolism of GABA into the Krebs cycle in rat pancreatic islets. Hern??ndez-Fisac, I., Fern??ndez-Pascual, S., Orts??ter, H., Pizarro-Delgado, J., Mart??n Del R??o, R., Bergsten, P., Tamarit-Rodriguez, J. Biochem. J. (2006) [Pubmed]
  16. NADP-specific isocitrate dehydrogenase in regulation of urea synthesis in rat hepatocytes. Petcu, L.G., Plaut, G.W. Biochem. J. (1980) [Pubmed]
  17. Combined effects of a metabolic inhibitor (gabaculine) and an uptake inhibitor (ketamine) on the gamma-aminobutyrate system in mouse brain. Wood, J.D., Geddes, J.W., Tsui, S.K., Kurylo, E. J. Neurochem. (1982) [Pubmed]
  18. Regulation of the gamma-aminobutyric acidA receptor by gamma-aminobutyric acid levels within the postsynaptic cell. Wood, J.D., Davies, M. J. Neurochem. (1989) [Pubmed]
  19. Amino acid content of nerve endings (synaptosomes) in different regions of brain: effects of gabaculine and isonicotinic acid hydrazide. Wood, J.D., Kurylo, E. J. Neurochem. (1984) [Pubmed]
  20. Activity-dependent transport of GABA analogues into specific cell types demonstrated at high resolution using a novel immunocytochemical strategy. Pow, D.V., Baldridge, W., Crook, D.K. Neuroscience (1996) [Pubmed]
  21. 2-amino-4-phosphonobutyric acid exerts a light-dependent effect on post-gabaculine levels of retinal gamma-aminobutyric acid (GABA): evidence that ON synaptic pathways regulate retinal GABAergic transmission. Cubells, J.F., Ndubuka, C., Makman, M.H. J. Neurochem. (1991) [Pubmed]
  22. Interactions of di-n-propylacetate, gabaculine, and aminooxyacetic acid: anticonvulsant activity and the gamma-aminobutyrate system. Wood, J.D., Kurylo, E., Tsui, S.K. J. Neurochem. (1981) [Pubmed]
  23. Haem synthesis during cytochrome P-450 induction in higher plants. 5-Aminolaevulinic acid synthesis through a five-carbon pathway in Helianthus tuberosus tuber tissues aged in the dark. Werck-Reichhart, D., Jones, O.T., Durst, F. Biochem. J. (1988) [Pubmed]
  24. Effect of inhibitors of GABA aminotransferase on the metabolism of GABA in brain tissue and synaptosomal fractions. Löscher, W. J. Neurochem. (1981) [Pubmed]
  25. Elevated endogenous GABA level correlates with decreased fMRI signals in the rat brain during acute inhibition of GABA transaminase. Chen, Z., Silva, A.C., Yang, J., Shen, J. J. Neurosci. Res. (2005) [Pubmed]
  26. Glutamyl-tRNA reductase of Chlorobium vibrioforme is a dissociable homodimer that contains one tightly bound heme per subunit. Srivastava, A., Beale, S.I. J. Bacteriol. (2005) [Pubmed]
  27. Gamma-aminobutyric acid turnover in rat striatum: effects of glutamate and kainic acid. Giorgi, O., Meek, J.L. J. Neurochem. (1984) [Pubmed]
  28. Formation of the chlorophyll precursor delta-aminolevulinic acid in cyanobacteria requires aminoacylation of a tRNAGlu species. O'Neill, G.P., Peterson, D.M., Schön, A., Chen, M.W., Söll, D. J. Bacteriol. (1988) [Pubmed]
  29. Biosynthesis of cytochrome f in Chlamydomonas reinhardtii: analysis of the pathway in gabaculine-treated cells and in the heme attachment mutant B6. Howe, G., Mets, L., Merchant, S. Mol. Gen. Genet. (1995) [Pubmed]
  30. On the neurotoxicity of chlordecone: a role for gamma-aminobutyric acid and serotonin. Gandolfi, O., Cheney, D.L., Hong, J.S., Costa, E. Brain Res. (1984) [Pubmed]
  31. GABA in the inferior colliculus plays a critical role in control of audiogenic seizures. Faingold, C.L., Marcinczyk, M.J., Casebeer, D.J., Randall, M.E., Arnerić, S.P., Browning, R.A. Brain Res. (1994) [Pubmed]
  32. Separation and partial characterization of enzymes catalyzing delta-aminolevulinic acid formation in Synechocystis sp. PCC 6803. Rieble, S., Beale, S.I. Arch. Biochem. Biophys. (1991) [Pubmed]
  33. An important role for endogenous synthesis of arginine in maintaining arginine homeostasis in neonatal pigs. Flynn, N.E., Wu, G. Am. J. Physiol. (1996) [Pubmed]
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