DL-AP4

Broad spectrum EAA antagonist CAS# 20263-07-4

DL-AP4

Catalog No. BCC6548----Order now to get a substantial discount!

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Chemical structure

DL-AP4

3D structure

Chemical Properties of DL-AP4

Cas No. 20263-07-4 SDF Download SDF
PubChem ID 2207 Appearance Powder
Formula C4H10NO5P M.Wt 183.1
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble to 33 mM in water
Chemical Name 2-amino-4-phosphonobutanoic acid
SMILES C(CP(=O)(O)O)C(C(=O)O)N
Standard InChIKey DDOQBQRIEWHWBT-UHFFFAOYSA-N
Standard InChI InChI=1S/C4H10NO5P/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H2,8,9,10)
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 DL-AP4

DescriptionBroad spectrum EAA ligand. Separate isomers D-AP4 and L-AP4 also available.

DL-AP4 Dilution Calculator

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DL-AP4 Molarity Calculator

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Preparing Stock Solutions of DL-AP4

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.4615 mL 27.3075 mL 54.615 mL 109.2299 mL 136.5374 mL
5 mM 1.0923 mL 5.4615 mL 10.923 mL 21.846 mL 27.3075 mL
10 mM 0.5461 mL 2.7307 mL 5.4615 mL 10.923 mL 13.6537 mL
50 mM 0.1092 mL 0.5461 mL 1.0923 mL 2.1846 mL 2.7307 mL
100 mM 0.0546 mL 0.2731 mL 0.5461 mL 1.0923 mL 1.3654 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 DL-AP4

Phenylglycines can evoke quisqualate-primed depolarizations in rat cingulate cortex: an effect associated with [3H]DL-AP4 uptake.[Pubmed:8996809]

Eur J Neurosci. 1996 Dec;8(12):2599-604.

Depolarization could be evoked in slices of rat cingulate cortex by the normally non-excitatory compound L-2-amino-4-phosphonobutyrate (L-AP4) if the slices had been sensitized by exposure to quisqualate. The magnitude of the response to L-AP4 was dependent on the concentrations of both L-AP4 and quisqualate and was inhibited by alpha-amino-3-hydroxy-5-methyl-4-isoxazole propionate receptor antagonism. A series of phenylglycine analogues were capable of evoking similar dose-dependent depolarizations in the rat cingulate cortex following quisqualate sensitization, the most potent being (S)-4-carboxy-3-hydroxyphenylglycine. If the superfusate collected during application of (S)-4-carboxy-3-hydroxyphenylglycine to a quisqualate-sensitized slice was administered to a slice not previously exposed to quisqualate, a small depolarization was obtained. All the compounds shown to be capable of evoking the quisqualate-sensitized response showed affinity for the L-AP4 uptake site whilst having no affinity at ionotropic glutamate receptors and different profiles of activity at metabotropic glutamate receptors. None of the compounds was active at the metabotropic glutamate 4a receptor. There was a statistically significant correlation between a compound's effectiveness in inhibiting [3H]DL-AP4 uptake into rat cortical synaptosomes and its potency in evoking quisqualate-sensitized depolarization. It is concluded that this response may be the result of hetero-exchange between L-AP4 ligands and quisqualate.

The effects of a series of omega-phosphonic alpha-carboxylic amino acids on electrically evoked and excitant amino acid-induced responses in isolated spinal cord preparations.[Pubmed:7042024]

Br J Pharmacol. 1982 Jan;75(1):65-75.

1 The depressant actions on evoked electrical activity and the excitant amino acid antagonist properties of a range of omega-phosphonic alpha-carboxylic amino acids have been investigated in the isolated spinal cord preparations of the frog or immature rat. 2 When tested on dorsal root-evoked ventral root potentials, members of the homologous series from 2- amino-5-phosphonovaleric acid to 2-amino-8-phosphonooctanoic acid showed depressant actions which correlated with the ability of the substances to antagonize selectivity motoneuronal depolarizations induced by N-methyl-D-aspartate. 3 2-Amino-5-phosphonovalerate was the most potent substance of the series giving an apparent KD of 1.4 microM for the antagonism of responses to N-methyl-D-aspartate. 4 A comparison of the (+)- and (-)-forms of 2-amino-5-phosphonovalerate indicated that the N-methyl-D-aspartate antagonist activity and the neuronal depressant action of this substance were both due mainly to the (-)-isomer. 5 The (-)- and (+)-forms of 2-amino-4-phosphonobutyrate had different actions. The (-)-forms of this substance had a relatively weak and non-selective antagonist action on depolarizations induced by N-methyl-D-aspartate, quisqualate and kainate and a similarly weak depressant effect when tested on evoked electrical activity. The (+)-form was more potent than he (-)-form in depressing electrically evoked activity but did not antagonize responses to amino acid excitants. At concentrations higher than those required to depress electrically evoked activity, the (+)-form produced depolarization. This action was blocked by 2-amino-5-phosphonovalerate.

Antagonism of excitatory amino acid-induced responses and of synaptic excitation in the isolated spinal cord of the frog.[Pubmed:316343]

Br J Pharmacol. 1979 Dec;67(4):591-603.

1. A range of compounds has been tested for excitatory amino acid agonist or antagonist activity and for effects on synaptic activity on isolated hemisected spinal cords of frogs. 2. L-Monoamino dicarboxylic acids of chain length up to 8 carbon atoms (L-alpha-aminosuberate) were all agonists. 3. Within a series of D-monoamino dicarboxylic acids, and with diamino dicarboxylic acids (mainly unresolved mixtures of diasteroisomers), there was a progression from agonist activity, for compounds of chain length equal to or shorter than glutamate, to antagonist activity, for compounds of longer chain length equal to or shorter than glutamate, to antagonist activity, for compounds of longer chain length, D-alpha-Aminosuberate (D alpha SD) was the most potent antagonist. 4. The antagonist actions of these substances showed a Mg2+--like selectivity with respect to depolarizations produced by different excitants. N-methyl-D-aspartate (NMDA) was the most susceptible agonist and quisqualate and kainate the least susceptible. Responses to other excitatory amino acids, including L-glutamate and L-aspartate, showed intermediate sensitivity to the antagonists. 5. A parallelism was observed between the relative potencies of mono- and diamino dicarboxylic acids as NMDA antagonists and their relative potencies as depressants of synaptic responses. 6. The results support the concept of different types of excitatory amino acid receptors, with NMDA and its antagonists acting predominantly on one type. These NMDA receptors are probably transmitter receptors activated by an excitatory amino acid transmitter.

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