(±)-HIP-A - CAS 227619-64-9
Category: Inhibitor
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Molecular Formula:
C6H8N2O4
Molecular Weight:
172.14
COA:
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Targets:
EAAT2
Description:
(±)-HIP-A is a potent and non-competitive excitatory amino acid transporter (EAAT) blocker. (±)-HIP-A displays no affinity for NMDA and metabotropic glutamate receptors, and weak affinity for AMPA and kainate receptors (IC50 = 43 and 8 μM, respectively). (±)-HIP-A inhibits glutamate-induced [3H]D-aspartate release (IC50 = 1.6 μM) rather than [3H]L-glutamate uptake (IC50 = 18 μM).
Brife Description:
EAAT blocker
Purity:
≥98% by HPLC
Synonyms:
(±)-3-Hydroxy-4,5,6,6a-tetrahydro-3aH-pyrrolo[3,4-d]isoxazole-4-carboxylic acid
MSDS:
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InChIKey:
XJSXFNHFIBCTDU-UHFFFAOYSA-N
InChI:
InChI=1S/C6H8N2O4/c9-5-3-2(12-8-5)1-7-4(3)6(10)11/h2-4,7H,1H2,(H,8,9)(H,10,11)
Canonical SMILES:
C1C2C(C(N1)C(=O)O)C(=O)NO2
1.Neuroprotective effects of the novel glutamate transporter inhibitor (-)-3-hydroxy-4,5,6,6a-tetrahydro-3aH-pyrrolo[3,4-d]-isoxazole-4-carboxylic acid, which preferentially inhibits reverse transport (glutamate release) compared with glutamate reuptake.
Colleoni S1, Jensen AA, Landucci E, Fumagalli E, Conti P, Pinto A, De Amici M, Pellegrini-Giampietro DE, De Micheli C, Mennini T, Gobbi M. J Pharmacol Exp Ther. 2008 Aug;326(2):646-56. doi: 10.1124/jpet.107.135251. Epub 2008 May 1.
(+/-)-3-Hydroxy-4,5,6,6a-tetrahydro-3aH-pyrrolo [3,4 -d]-isoxazole-4-carboxylic acid (HIP-A) and (+/-)-3-hydroxy-4,5,6, 6a-tetrahydro-3aH-pyrrolo[3,4-d]isoxazole-6-carboxylic acid (HIP-B) are selective inhibitors of excitatory amino acid transporters (EAATs), as potent as DL-threo-beta-benzyloxyaspartic acid (TBOA). We report here that the active isomers are (-)-HIP-A and (+)-HIP-B, being approximately 150- and 10-fold more potent than the corresponding enantiomers as inhibitors of [3H]aspartate uptake in rat brain synaptosomes and hEAAT1-3-expressing cells. Comparable IC(50) values were found on the three hEAAT subtypes. (-)-HIP-A maintained the remarkable property, previously reported with the racemates, of inhibiting synaptosomal glutamate-induced [3H]D-aspartate release (reverse transport) at concentrations significantly lower than those inhibiting [3H]L-glutamate uptake. New data suggest that the noncompetitive-like interaction described previously is probably the consequence of an insurmountable, long-lasting impairment of EAAT's function.
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