L-DABA hydrobromide

Names

[ Name ]:
L-DABA hydrobromide

[Synonym ]:
(S)-2,4-bis-benzyloxycarbonylamino-butyric acid
(S)-2,4-Bis-benzyloxycarbonylamino-buttersaeure
(S)-2,4-diamino-butyric acid,hydrobromide
(2S)-2,4-Diaminobutanoic acid hydrobromide (1:1)
Butanoic acid, 2,4-diamino-, (2S)-, hydrobromide (1:1)
(S)-2,4-Diamino-buttersaeure,Hydrobromid
N,N'-Cbz-L-2,4-diaminobutanoic acid
Z-DAB(Z)-OH

Biological Activity

[Description]:

L-DABA (L-2,4-Diaminobutyric acid) hydrobromide is a week GABA transaminase inhibitor with an IC50 of larger than 500 μM; exhibits antitumor activity in vivo and in vitro.

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor

Research Areas >> Neurological Disease

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

[Target]

IC50: larger than 500 μM (GABA transaminase)[1]

[In Vitro]

The tumor cells are irreversibly and totally damaged by incubation with 10 mM L-2,4-Diaminobutyric acid for 24 h at 37°C. The cell-destructive effect by L-DABA hydrobromide is probably due to an osmotic lysis induced by the non-saturated intracellular accumulation of L-DABA hydrobromide. The harmful effect of L-DABA hydrobromide could be abolished by concomitant incubation with L-alanine and L-methionine[1]. Kinetic studies indicates that L-DABA hydrobromide is a non-linear, non-competitive inhibitor of GABA transaminase activity. The L-DABA hydrobromide-induced elevation of GABA levels parallels the inhibition of GABA transaminase activity[2]. L-2,4-Diaminobutyric acid, an amino acid analogue, produceS a cytolytic effect with a human glioma cell line, SKMG-1, and normal human fibroblasts. The concentrations of L-DABA hydrobromide necessary to reduce the cell count to 50% of control following a 24-h incubation at 37°C are 12.5 mM for the human fibroblasts and 20 mM for the glioma cell line[3].

[In Vivo]

Treatment with L-DABA hydrobromide results in 43.4% reduction of tumor growth[1]. L-DABA hydrobromide is a more effective inhibitor of GABA transaminase in vivo than in vitro[2].

[References]

[1]. Ronquist G, et al. Antitumor activity of L-2,4 diaminobuturic acid against mouse fibrosarcoma cells in vitro and in vivo. J Cancer Res Clin Oncol. 1980;96(3):259-68.

[2]. Beart PM, et al. l-2,4-Diaminobutyric acid and the GABA system. Neurosci Lett. 1977 Jul;5(3-4):193-8.

[3]. Panasci L, et al. The cytolytic effect of L-2,4 diaminobutyric acid with malignant glioma cells and fibroblasts. Cancer Chemother Pharmacol. 1988;21(2):143-4.

Chemical & Physical Properties

[ Molecular Formula ]:
C₄H₁₁BrN₂O₂

[ Molecular Weight ]:
199.05

[ Exact Mass ]:
198.000381

[ PSA ]:
89.34000

[ LogP ]:
1.10580

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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