| Identification | Back Directory | [Name]
L-TRANS-PYRROLIDINE-2,4-DICARBOXYLIC ACID | [CAS]
64769-66-0 | [Synonyms]
4-PDC
L-trans-2
Zinc03796127
L-TRANS-2,4-PDC
TRANS-4-CARBOXY-L-PROLINE
L-TRANS-4-CARBOXY-L-PROLINE
(2S,4R)-2,4-Pyrrolidinedicarboxylic acid
(2S,4R)-pyrrolidine-2,4-dicarboxylic acid
L-TRANS-PYRROLIDINE-2,4-DICARBOXYLIC ACID
2,4-Pyrrolidinedicarboxylic acid, (2S,4R)-
2,4-Pyrrolidinedicarboxylicacid,(2S,4R)-(9CI) | [Molecular Formula]
C6H9NO4 | [MDL Number]
MFCD00153866 | [MOL File]
64769-66-0.mol | [Molecular Weight]
159.14 |
| Chemical Properties | Back Directory | [Melting point ]
214-217oC | [storage temp. ]
Store at RT | [solubility ]
Water (Slightly) | [form ]
White solid. | [color ]
White | [Water Solubility ]
Soluble to 100 mM in water | [InChI]
InChI=1S/C6H9NO4/c8-5(9)3-1-4(6(10)11)7-2-3/h3-4,7H,1-2H2,(H,8,9)(H,10,11)/t3-,4+/m1/s1 | [InChIKey]
NRSBQSJHFYZIPH-DMTCNVIQSA-N | [SMILES]
N1C[C@H](C(O)=O)C[C@H]1C(O)=O |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38 | [Safety Statements ]
26-36 | [WGK Germany ]
3 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Description]
L-trans-Pyrrolidine-2,4-dicarboxylic acid (L-trans-2,4-PDC) is an inhibitor of L-glutamate transport (Ki = 4.6 μM in rat brain synaptosomes). It inhibits radioligand binding to NMDA receptors by 13% but has no effect on AMPA or kainate receptors when used at a concentration of 100 μM. L-trans-2,4-PDC is neurotoxic to astrocyte-rich and astrocyte-poor rat cortical cultures (EC50s = 320 and 50 μM, respectively), an effect that can be reversed by the NMDA antagonist MK-801 and glutamate-pyruvate transaminase but not the non-NMDA glutamate receptor antagonist CNQX. It induces efflux of the non-metabolizable glutamate analog [3H]-D-aspartate in an extracellular sodium-dependent manner. In vivo, L-trans-2,4-PDC (0.05-0.2 μg/side) prevents amphetamine-induced hyperlocomotion in a dose-dependent manner in rats when injected directly into the nucleus accumbens. It also increases bladder intercontraction interval (ICI) without affecting postvoid residual or basal pressure in rats. | [Uses]
L-trans-Pyrrolidine-2,4-dicarboxylic Acid is an inhibitor of the glutamate transporter EAAT. | [Biological Activity]
Potent, competitive, transportable EAAT1-4 inhibitor/non-transportable EAAT5 inhibitor. Also available as part of the Excitatory Amino Acid Transporter Inhibitor Tocriset™ . | [storage]
Store at -20°C | [References]
[1] RICHARD J. BRIDGES. Conformationally defined neurotransmitter analogs. Selective inhibition of glutamate uptake by one pyrrolidine-2,4-dicarboxylate diastereomer[J]. Journal of Medicinal Chemistry, 1991, 34 2: 717-725. DOI:10.1021/jm00106a037.
[2] Blitzblau, R., Gupta, S., Djali, S., et al. The glutamate transport inhibitor L-trans-pyrrolidine-2,4-dicarboxylate indirectly evokes NMDA receptor mediated neurotoxicity in rat cortical cultures. Eur. J. Neurosci. 8(9), 1840-1852 (1996).
[3] David, H.N., Thévenoux, A., and Abraini, J.H. Inhibition of the glutamate transporter by L-trans-PDC in the nucleus accumbens prevents the locomotor response to amphetamine. Neuropharmacology 41(3), 409-411 (2001).
[4] MASASHI HONDA. Supraspinal and spinal effects of L-trans-PDC, an inhibitor of glutamate transporter, on the micturition reflex in rats.[J]. Neurourology and Urodynamics, 2013, 32 7: 1026-1030. DOI:10.1002/nau.22351. |
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