Synonym
DL-TBOA; DLTBOA; DL TBOA
IUPAC/Chemical Name
(2S,3S)-2-amino-3-phenylmethoxybutanedioic acid
InChi Key
BYOBCYXURWDEDS-IUCAKERBSA-N
InChi Code
InChI=1S/C11H13NO5/c12-8(10(13)14)9(11(15)16)17-6-7-4-2-1-3-5-7/h1-5,8-9H,6,12H2,(H,13,14)(H,15,16)/t8-,9-/m0/s1
SMILES Code
OC([C@@H](N)[C@@H](C(O)=O)OCC1=CC=CC=C1)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
DL-TBOA is a potent non-transportable inhibitor of excitatory amino acid transporters with IC50s of 70 μM, 6 μM and 6 μM for excitatory amino acid transporter-1 (EAAT1), EAAT2 and EAAT3, respectively.
In vitro activity:
In EAAT4-expressing oocytes, D,L-TBOA acted as a non-transportable blocker, while L-TMOA like D,L-THA was a competitive substrate. In contrast, D,L-THA, D,L-TBOA and L-TMOA all strongly attenuated the glutamate-induced currents generated by EAAT5. Among them, L-TMOA showed the most potent inhibitory action. Moreover, D,L-THA, D,L-TBOA and L-TMOA themselves elicited outward currents at negative potentials and remained inward at positive potentials suggesting that D,L-TBOA and L-TMOA, as well as D,L-THA, not only act as non-transportable blockers, but also block the EAAT5 leak currents.
Reference: J Neurochem. 2001 Oct;79(2):297-302. https://pubmed.ncbi.nlm.nih.gov/11677257/
In vivo activity:
At 8 weeks of age, the mice showed impairments in cognitive or emotional behaviors; dysfunction of glutamatergic neurotransmission (increased expressions of GLAST, GLT-1, or GFAP protein, and decreased ability of glutamate release) in the cortex or hippocampus; morphological changes (decreased cell size in the cortex and thickness of the pyramidal neuronal layer of the CA1 area in the hippocampus). Such behavioral and morphological changes were not observed in adult mice injected with dl-TBOA. These results suggest that GLAST plays an important role in the regulation of cognitive and emotional behaviors.
Reference: Neurochem Int. 2021 Nov;150:105177. https://pubmed.ncbi.nlm.nih.gov/34481039/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
112.0 |
468.01 |
| Water |
3.1 |
12.96 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
239.23
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Shigeri Y, Shimamoto K, Yasuda-Kamatani Y, Seal RP, Yumoto N, Nakajima T, Amara SG. Effects of threo-beta-hydroxyaspartate derivatives on excitatory amino acid transporters (EAAT4 and EAAT5). J Neurochem. 2001 Oct;79(2):297-302. doi: 10.1046/j.1471-4159.2001.00588.x. PMID: 11677257.
2. Shimamoto K, Lebrun B, Yasuda-Kamatani Y, Sakaitani M, Shigeri Y, Yumoto N, Nakajima T. DL-threo-beta-benzyloxyaspartate, a potent blocker of excitatory amino acid transporters. Mol Pharmacol. 1998 Feb;53(2):195-201. doi: 10.1124/mol.53.2.195. PMID: 9463476.
3. Uchida M, Noda Y, Hasegawa S, Hida H, Taniguchi M, Mouri A, Yoshimi A, Nabeshima T, Yamada K, Aida T, Tanaka K, Ozaki N. Early postnatal inhibition of GLAST causes abnormalities of psychobehaviors and neuronal morphology in adult mice. Neurochem Int. 2021 Nov;150:105177. doi: 10.1016/j.neuint.2021.105177. Epub 2021 Sep 1. PMID: 34481039.
4. Wang CC, Kuo JR, Wang SJ. Fingolimod inhibits glutamate release through activation of S1P1 receptors and the G protein βγ subunit-dependent pathway in rat cerebrocortical nerve terminals. Neuropharmacology. 2021 Mar 1;185:108451. doi: 10.1016/j.neuropharm.2021.108451. Epub 2021 Jan 9. PMID: 33428887.
In vitro protocol:
1. Shigeri Y, Shimamoto K, Yasuda-Kamatani Y, Seal RP, Yumoto N, Nakajima T, Amara SG. Effects of threo-beta-hydroxyaspartate derivatives on excitatory amino acid transporters (EAAT4 and EAAT5). J Neurochem. 2001 Oct;79(2):297-302. doi: 10.1046/j.1471-4159.2001.00588.x. PMID: 11677257.
2. Shimamoto K, Lebrun B, Yasuda-Kamatani Y, Sakaitani M, Shigeri Y, Yumoto N, Nakajima T. DL-threo-beta-benzyloxyaspartate, a potent blocker of excitatory amino acid transporters. Mol Pharmacol. 1998 Feb;53(2):195-201. doi: 10.1124/mol.53.2.195. PMID: 9463476.
In vivo protocol:
1. Uchida M, Noda Y, Hasegawa S, Hida H, Taniguchi M, Mouri A, Yoshimi A, Nabeshima T, Yamada K, Aida T, Tanaka K, Ozaki N. Early postnatal inhibition of GLAST causes abnormalities of psychobehaviors and neuronal morphology in adult mice. Neurochem Int. 2021 Nov;150:105177. doi: 10.1016/j.neuint.2021.105177. Epub 2021 Sep 1. PMID: 34481039.
2. Wang CC, Kuo JR, Wang SJ. Fingolimod inhibits glutamate release through activation of S1P1 receptors and the G protein βγ subunit-dependent pathway in rat cerebrocortical nerve terminals. Neuropharmacology. 2021 Mar 1;185:108451. doi: 10.1016/j.neuropharm.2021.108451. Epub 2021 Jan 9. PMID: 33428887.
1. Shimamoto, K., Lebrun, B., Yasuda-Kamatani, Y., et al. ᴅʟ-threo-β-benzyloxyaspartate, a potent blocker of excitatory amino acid transporters. Mol. Pharmacol. 53(2), 195-201 (1998).
2. Shigeri, Y., Shimamoto, K., Yasuda-Kamatani, Y., et al. Effects of threo-β-hydroxyaspartate derivatives on excitatory amino acid transporters (EAAT4 and EAAT5). J. Neurochem. 79(2), 297-302 (2001).
3. Montiel, T., Camacho, A., Estrada-Sánchez, A.M., et al. Differential effects of the substrate inhibitor ʟ-trans-pyrrolidine-2,4-dicarboxylate (PDC) and the non-substrate inhibitor ᴅʟ-threo-β-benzyloxyaspartate (ᴅʟ-TBOA) of glutamate transporters on neuronal damage and extracellular amino acid levels in rat brain in vivo. Neuroscience 133(3), 667-678 (2005).
4. Yaster, M., Guan, X., Petralia, R.S., et al. Effect of inhibition of spinal cord glutamate transporters on inflammatory pain induced by formalin and complete Freund’s adjuvant. Anesthesiology 114(2), 412-423 (2011).
