Z-Cyclopentyl-AP4Group III mGlu agonist (mGlu4 > mGlu8 > mGlu7) CAS# 103439-17-4 |
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 103439-17-4 | SDF | Download SDF |
| PubChem ID | 56972223 | Appearance | Powder |
| Formula | C6H12NO5P | M.Wt | 209.14 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble to 50 mM in 1.1eq. NaOH | ||
| Chemical Name | (1S,3R)-1-amino-3-phosphonocyclopentane-1-carboxylic acid;(1R,3S)-1-amino-3-phosphonocyclopentane-1-carboxylic acid | ||
| SMILES | C1CC(CC1P(=O)(O)O)(C(=O)O)N.C1CC(CC1P(=O)(O)O)(C(=O)O)N | ||
| Standard InChIKey | GLBQBTFFQHNHGC-RPBIHNRISA-N | ||
| Standard InChI | InChI=1S/2C6H12NO5P/c2*7-6(5(8)9)2-1-4(3-6)13(10,11)12/h2*4H,1-3,7H2,(H,8,9)(H2,10,11,12)/t2*4-,6+/m10/s1 | ||
| 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. |
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| 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. |
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| 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. | ||
| Description | Group III mGlu receptor agonist that exhibits higher potency at mGlu4 than mGlu8 (EC50 values are 49 and 124 μM respectively) with no activity at mGlu7. Selectively inhibits synaptic activity in the lateral perforant pathway (IC50 values are 130 and 1859 μM in the lateral and medial perforant pathways respectively). Conformationally restrained analog of L-AP4. |
Z-Cyclopentyl-AP4 Dilution Calculator
Z-Cyclopentyl-AP4 Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 4.7815 mL | 23.9074 mL | 47.8149 mL | 95.6297 mL | 119.5372 mL |
| 5 mM | 0.9563 mL | 4.7815 mL | 9.563 mL | 19.1259 mL | 23.9074 mL |
| 10 mM | 0.4781 mL | 2.3907 mL | 4.7815 mL | 9.563 mL | 11.9537 mL |
| 50 mM | 0.0956 mL | 0.4781 mL | 0.9563 mL | 1.9126 mL | 2.3907 mL |
| 100 mM | 0.0478 mL | 0.2391 mL | 0.4781 mL | 0.9563 mL | 1.1954 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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Metabotropic glutamate receptors mGluR4 and mGluR8 regulate transmission in the lateral olfactory tract-piriform cortex synapse.[Pubmed:18625254]
Neuropharmacology. 2008 Sep;55(4):440-6.
The piriform cortex (PC) is the primary terminal zone of projections from the olfactory bulb, termed the lateral olfactory tract (LOT). The PC plays a critical role in processing of olfactory stimuli and is also a highly seizure prone area thought to be involved in some forms of temporal lobe epilepsy. Pharmacological and immunohistochemical studies provide evidence for the localization of various metabotropic glutamate receptors (GluRs) in the PC. We employed whole-cell patch clamp recordings from PC pyramidal cells to determine the roles of group III mGluRs in modulating synaptic transmission at the LOT-PC synapse. The group III mGluR agonist, L-AP4, induced a concentration-dependent inhibition of synaptic transmission at the LOT-PC synapse at concentrations that activate mGluR4 and mGluR8, but not mGluR7 or other mGluR subtypes (EC50=473nM). In addition, the selective mGluR8 agonist, DCPG (300nM), also suppressed synaptic transmission at the LOT synapse. Furthermore, the inhibitory actions of L-AP4 and Z-Cyclopentyl-AP4, a selective mGluR4 agonist, were potentiated by the mGluR4 positive allosteric modulator, PHCCC (30microM). The high potency of L-AP4, combined with the observed effects of DCPG and PHCCC, suggests that both mGluR4 and mGluR8 play a role in the l-AP4-induced inhibition of synaptic transmission at the LOT-PC synapse.
Group III mGluR regulation of synaptic transmission at the SC-CA1 synapse is developmentally regulated.[Pubmed:18255102]
Neuropharmacology. 2008 Apr;54(5):804-14.
Group III metabotropic glutamate receptors (mGluRs) reduce synaptic transmission at the Schaffer collateral-CA1 (SC-CA1) synapse in rats by a presynaptic mechanism. Previous studies show that low concentrations of the group III-selective agonist, L-AP4, reduce synaptic transmission in slices from neonatal but not adult rats, whereas high micromolar concentrations reduce transmission in both age groups. L-AP4 activates mGluRs 4 and 8 at much lower concentrations than those required to activate mGluR7, suggesting that the group III mGluR subtype modulating transmission is a high affinity receptor in neonates and a low affinity receptor in adults. The previous lack of subtype selective ligands has made it difficult to test this hypothesis. We have measured fEPSPs in the presence of novel subtype selective agents to address this question. We show that the effects of L-AP4 can be blocked by LY341495 in both neonates and adults, verifying that these effects are mediated by mGluRs. In addition, the selective mGluR8 agonist, DCPG, has a significant effect in slices from neonatal rats but does not reduce synaptic transmission in adult slices. The mGluR4 selective allosteric potentiator, PHCCC, is unable to potentiate the L-AP4-induced effects at either age. Taken together, our data suggest that group III mGluRs regulate transmission at the SC-CA1 synapse throughout development but there is a developmental regulation of the subtypes involved so that both mGluR7 and mGluR8 serve this role in neonates whereas mGluR7 is involved in regulating transmission at this synapse throughout postnatal development.
Cyclic analogues of 2-amino-4-phosphonobutanoic acid (APB) and their inhibition of hippocampal excitatory transmission and displacement of [3H]APB binding.[Pubmed:3020251]
J Med Chem. 1986 Oct;29(10):1988-95.
Conformationally restricted analogues of 2-amino-4-phosphonobutanoic acid (APB,2) were prepared where the structure of APB was incorporated into cyclopentane (3) or cyclohexane (4) rings. Hydrophosphinylation of the appropriate cycloalkenones followed by Strecker amino acid syntheses provided the desired analogues. Assignments of the relative configurations for 3a (trans), 3b (cis), 4a (cis), and 4b (trans) were determined through 13C NMR studies. Compounds 3b, 4a, and 4b possessed low activity as inhibitors of excitatory synaptic field potentials in the rat hippocampal perforant path. Analogues 4a and 4b also showed little activity in displacing [3H]APB from synaptic plasma membranes. The cyclopentyl APB analogue 36, on the other hand, was extremely potent in inhibiting the binding of [3H]APB, possessing an IC50 = 4.7 microM, thus giving further credence to the idea that the APB binding site in the rat brain synaptosomal membrane preparation is not the same as the receptor mediating APB-induced inhibition of the lateral perforant path. Of the four cyclic APB analogues, 3a most resembled APB in its spectrum of biological activity. It showed significant potency (IC50 = 130 microM) in inhibiting lateral entorhinal projections to hippocampal granule cells. Analogous to APB, 3a also showed selectivity for the lateral perforant path over the medial perforant path. Its activity in the radioligand binding assay paralleled its activity in inhibiting the lateral perforant path. It thus appears that 3a comes closest to mimicking the active conformation of APB and suggests that a folded conformation wherein the amino and phosphonate moieties are in a cis relationship to one another may approximate the active conformation of APB.
