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3-MATIDA

Potent, selective mGlu1 antagonist CAS# 518357-51-2

3-MATIDA

Catalog No. BCC7281----Order now to get a substantial discount!

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Chemical structure

3-MATIDA

3D structure

Chemical Properties of 3-MATIDA

Cas No. 518357-51-2 SDF Download SDF
PubChem ID 10398360 Appearance Powder
Formula C8H9NO4S M.Wt 215.23
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble to 100 mM in 1eq. NaOH and to 50 mM in DMSO
Chemical Name 5-[amino(carboxy)methyl]-4-methylthiophene-2-carboxylic acid
SMILES CC1=C(SC(=C1)C(=O)O)C(C(=O)O)N
Standard InChIKey KOMWRBFEDDEWEP-UHFFFAOYSA-N
Standard InChI InChI=1S/C8H9NO4S/c1-3-2-4(7(10)11)14-6(3)5(9)8(12)13/h2,5H,9H2,1H3,(H,10,11)(H,12,13)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of 3-MATIDA

DescriptionPotent metabotropic glutamate mGlu1 receptor antagonist (IC50 = 6.3 μM at rat mGlu1a). Displays ≥ 40-fold selectivity over other receptors: mGlu5, mGlu2, mGlu4a (IC50 > 300 μM), NMDA and AMPA (IC50 = 250 μM). Neuroprotective in cultured murine cortical cells and rat hippocampal slice cultures in vitro. Reduces the volume of ischemia-induced brain infarcts in rats following systemic administration in vivo.

3-MATIDA Dilution Calculator

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3-MATIDA Molarity Calculator

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Preparing Stock Solutions of 3-MATIDA

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.6462 mL 23.231 mL 46.4619 mL 92.9238 mL 116.1548 mL
5 mM 0.9292 mL 4.6462 mL 9.2924 mL 18.5848 mL 23.231 mL
10 mM 0.4646 mL 2.3231 mL 4.6462 mL 9.2924 mL 11.6155 mL
50 mM 0.0929 mL 0.4646 mL 0.9292 mL 1.8585 mL 2.3231 mL
100 mM 0.0465 mL 0.2323 mL 0.4646 mL 0.9292 mL 1.1615 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 3-MATIDA

Stereoselective synthesis and preliminary evaluation of (+)- and (-)-3-methyl-5-carboxy-thien-2-yl-glycine (3-MATIDA): identification of (+)-3-MATIDA as a novel mGluR1 competitive antagonist.[Pubmed:14871500]

Farmaco. 2004 Feb;59(2):93-9.

The synthesis of the (+)- and (-)-isomers of 3-methyl-5-carboxy-thyen-2-yl-glycine (3-MATIDA), heterocyle isosters of carboxyphenylglycines (CPGs), a known class of competitive metabotropic glutamate receptors, was accomplished by a stereoselective Ugi condensation. The two isomers were tested as potential rat mGluR1 ligand and the (+) isomer was found to be a moderately potent antagonist, while the (-) one was inactive.

The novel and systemically active metabotropic glutamate 1 (mGlu1) receptor antagonist 3-MATIDA reduces post-ischemic neuronal death.[Pubmed:12015200]

Neuropharmacology. 2002 May;42(6):741-51.

We examined the pharmacological properties of 3-methyl-aminothiophene dicarboxylic acid (3-MATIDA) by measuring second messenger responses in baby hamster kidney cells stably transfected with mGlu1a, mGlu2, mGlu4a or mGlu5a receptors and ionotropic glutamate receptor agonist-induced depolarizations in mouse cortical wedges. 3-MATIDA was a potent (IC(50)=6.3 microM, 95% confidence limits 3-15) and relatively selective mGlu1 receptor antagonist. When tested on mGlu2, mGlu4 or mGlu5 receptors its IC(50) was >300 microM. When tested in cortical wedges, however, 3-MATIDA was also able to antagonize AMPA or NMDA responses with an IC(50) of 250 microM. When present in the incubation medium of cultured murine cortical cells, 3-MATIDA (1-100 microM) significantly reduced the death of neurons induced by 60 min of oxygen and glucose deprivation (OGD), even when added up to 60 min after OGD. A similar neuroprotective activity was observed when 3-MATIDA was present at 10-100 microM in the medium of rat organotypic hippocampal slice cultures exposed to 30 min OGD. Systemic administration of 3-MATIDA (3-10 mg/kg, immediately and 1 h after the onset of ischemia) reduced the volume of brain infarcts following permanent middle cerebral artery occlusion in rats. Our results show that 3-MATIDA is a potent and possibly selective mGlu 1 receptor antagonist that may be considered as a novel prototype neuroprotective agent.

Metabotropic glutamate 1 (mGlu1) receptor antagonists enhance GABAergic neurotransmission: a mechanism for the attenuation of post-ischemic injury and epileptiform activity?[Pubmed:12213266]

Neuropharmacology. 2002 Aug;43(2):119-30.

Selective antagonists of mGlu1 metabotropic glutamate receptors attenuate neuronal death in models of cerebral ischemia. Because GABAergic mechanisms have recently been proposed to contribute to these neuroprotective effects, we examined the effects of selective mGlu1 antagonists characterized in our laboratory on GABAergic transmission in three different models of neuropathology. In rat organotypic hippocampal slices exposed to oxygen-glucose deprivation, the mGlu1 antagonists AIDA, CBPG and 3-MATIDA reduced CA1 pyramidal cell loss when added to the medium during the insult and the subsequent recovery period. This effect was mimicked by the GABA(A) and GABA(B) agonists muscimol and baclofen and partially prevented by the antagonists bicuculline and CGP 55845. In gerbils subjected to global ischemia, protection of CA1 pyramidal cells by transdialytic perfusion of AIDA and CBPG was associated with a significant increase in the basal and ischemic output of GABA and minor changes in the output of glutamate. In a mouse cortical wedge model, both muscimol and 3-MATIDA reduced the frequency of spontaneous bursts induced by 4-aminopyridine and this reduction was prevented by co-perfusion with bicuculline. Taken together, our results suggest that the release of GABA, and the subsequent activation of GABA receptors, may contribute to the attenuation of post-ischemic neuronal damage and epileptiform activity induced by mGlu1 receptor antagonists.

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