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L-DABA hydrobromide (L-2,4-Diaminobutyric acid; L-2,4-Diaminobutyric acid hydrobromide) 73143-97-2

L-DABA hydrobromide (L-2,4-Diaminobutyric acid; L-2,4-Diaminobutyric acid hydrobromide) 73143-97-2

CAS No.: 73143-97-2

L-DABA (L-2,4-Diaminobutyric acid) HBr is a weak inhibitor of GABA transaminase, with IC50 greater than 500 μM. It has
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L-DABA (L-2,4-Diaminobutyric acid) HBr is a weak inhibitor of GABA transaminase, with IC50 greater than 500 μM. It has anticancer effect in vivo and in vitro.

Physicochemical Properties


Molecular Formula C4H11BRN2O2
Molecular Weight 199.05
Exact Mass 198
CAS # 73143-97-2
PubChem CID 46735201
Appearance White to off-white solid powder
LogP 1.105
Hydrogen Bond Donor Count 4
Hydrogen Bond Acceptor Count 4
Rotatable Bond Count 3
Heavy Atom Count 9
Complexity 84.1
Defined Atom Stereocenter Count 1
SMILES

C(CN)[C@@H](C(=O)O)N.Br

InChi Key RVCHWEZQMFNGBK-DFWYDOINSA-N
InChi Code

InChI=1S/C4H10N2O2.BrH/c5-2-1-3(6)4(7)8;/h3H,1-2,5-6H2,(H,7,8);1H/t3-;/m0./s1
Chemical Name

(2S)-2,4-diaminobutanoic acid;hydrobromide
HS Tariff Code 2934.99.9001
Storage

Powder-20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity


Targets IC50: larger than 500 μM (GABA transaminase)[1]
ln Vitro An incubation period of 24 hours at 37°C with 10 mM L-2,4-Diaminobutyric acid completely destroys the tumor cells. The osmotic lysis that results from the non-saturated intracellular buildup of L-DABA hydrobromide is most likely the cause of the cell-destructive action of L-DABA hydrobromide. L-alanine and L-methionine could be incubated together concurrently to eliminate the negative effects of L-DABA hydrobromide[1]. L-DABA hydrobromide is a non-linear, non-competitive inhibitor of GABA transaminase activity, according to kinetic studies. GABA levels are raised in response to L-DABA hydrobromide, which also inhibits GABA transaminase activity[2]. An amino acid analogue called L-2,4-Diaminobutyric acid exhibits cytolytic effects on the human glioma cell line SKMG-1 as well as normal human fibroblasts. After a 24-hour incubation at 37°C, the doses of L-DABA hydrobromide required to lower the cell count to 50% of control are 12.5 mM for human fibroblasts and 20 mM for the glioma cell line[3].
ln Vivo The development of tumors is reduced by 43.4% when treated with L-DABA hydrobromide[1]. In vivo GABA transaminase inhibition is more potent than in vitro inhibition when using L-DABA hydrobromide[2].
References

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

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


Solubility Data


Solubility (In Vitro) May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo) Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 :Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300:Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)

Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.0239 mL 25.1193 mL 50.2386 mL
5 mM 1.0048 mL 5.0239 mL 10.0477 mL
10 mM 0.5024 mL 2.5119 mL 5.0239 mL
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.