Molecular structure of Gabaculine, CAS Number: 59556-17-1
Gabaculine (CAS 59556-17-1)
See product citations (5)
Alternate Names:
5-Amino-1,3-cyclohexadiene-1-carboxylic Acid Hydrochloride; 3-Amino-2,3-dihydrobenzoic Acid;
Application:
Gabaculine is a conformationally constrained analog of GABA
CAS Number:
59556-17-1
Purity:
≥95%
Molecular Weight:
175.61
Molecular Formula:
C7H9NO2•HCl
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
Gabaculine is a conformationally constrained analog of gamma-aminobutyric acid (GABA). It acts as an irreversible and potent inhibitor of GABA transaminase, the enzyme that converts GABA in the brain into succinate semialdehyde that can enter the citric acid cycle. Gabaculine is a substrate of the GABA Receptor. It can be found in chlorophyll. It has demonstrated the ability to inhibit the function of aminotransferase enzymes and exhibits antimicrobial properties against gram-positive bacteria, including Staphylococcus aureus. Additionally, it may act to inhibit glutamate receptors and target enzymes for glutamine metabolism.
Gabaculine (CAS 59556-17-1) References
- Gabaculine does not inhibit cytokinin-stimulated biosynthesis of chlorophyll in Pinus nigra seedlings in the dark. | Drazic, G. and Bogdanovic, M. 2000. Plant Sci. 154: 23-29. PMID: 10725555
- Glutamine is the major precursor for GABA synthesis in rat neocortex in vivo following acute GABA-transaminase inhibition. | Patel, AB., et al. 2001. Brain Res. 919: 207-20. PMID: 11701133
- Biosynthesis and distribution of chlorophyll among the photosystems during recovery of the green alga Dunaliella salina from irradiance stress. | Masuda, T., et al. 2002. Plant Physiol. 128: 603-14. PMID: 11842163
- Elevated endogenous GABA level correlates with decreased fMRI signals in the rat brain during acute inhibition of GABA transaminase. | Chen, Z., et al. 2005. J Neurosci Res. 79: 383-91. PMID: 15619231
- MK-801 enhances gabaculine-induced loss of the righting reflex in mice, but not immobility. | Irifune, M., et al. 2007. Can J Anaesth. 54: 998-1005. PMID: 18056209
- Gabaculine alters plastid development and differentially affects abundance of plastid-encoded DPOR and nuclear-encoded GluTR and FLU-like proteins in spruce cotyledons. | Demko, V., et al. 2010. J Plant Physiol. 167: 693-700. PMID: 20129699
- Necessary and sufficient conditions for the asymmetric synthesis of chiral amines using ω-aminotransferases. | Seo, JH., et al. 2011. Biotechnol Bioeng. 108: 253-63. PMID: 20824676
- A point mutation in the Medicago sativa GSA gene provides a novel, efficient, selectable marker for plant genetic engineering. | Ferradini, N., et al. 2011. J Biotechnol. 156: 147-52. PMID: 21875626
- A mutant Synechococcus gene encoding glutamate 1-semialdehyde aminotransferase confers gabaculine resistance when expressed in tobacco plastids. | Bellucci, M., et al. 2015. Plant Cell Rep. 34: 2127-36. PMID: 26265112
- Intracellular sources of ornithine for polyamine synthesis in endothelial cells. | Li, H., et al. 2016. Amino Acids. 48: 2401-10. PMID: 27180260
- The indirect γ-aminobutyric acid (GABA) receptor agonist gabaculine-induced loss of the righting reflex may inhibit the descending analgesic pathway. | Ogawa, Y., et al. 2020. Pharmacol Biochem Behav. 198: 173034. PMID: 32910929
- Inhibitors of GABA metabolism. | Metcalf, BW. 1979. Biochem Pharmacol. 28: 1705-12. PMID: 383082
- Mechanism of the irreversible inhibition of gamma-aminobutyric acid-alpha-ketoglutaric acid transaminase by the neutrotoxin gabaculine. | Rando, RR. 1977. Biochemistry. 16: 4604-10. PMID: 410442
- A comparative study of the pharmacology of inhibitors of GABA-metabolism. | Löscher, W. 1980. Naunyn Schmiedebergs Arch Pharmacol. 315: 119-28. PMID: 6782493
Inhibitor of:
AASS, AGAT, AGXT2L1, AGXT2L2, BBOX1, BGT-1, CSAD, GAD-25, GCAT, Gm853, GNA1, Inhibitors, LAAO, PCLN-1, PDXDC1, PDXDC2, PSAT1, TAT1, Trp E, and UROS.Activator of:
Bestatin, and GABA T-2.Substrate of:
GABA Receptor.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Gabaculine, 10 mg | sc-200473 | 10 mg | $347.00 | |||
Gabaculine, 50 mg | sc-200473A | 50 mg | $867.00 | |||
Gabaculine, 250 mg | sc-200473B | 250 mg | $3009.00 |