(1S,3R)-ACPD - CAS 111900-32-4
Category: Inhibitor
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Molecular Formula:
C7H11NO4
Molecular Weight:
173.17
COA:
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Targets:
mGluR
Description:
(1S,3R)-ACPD, an isomer of (±)-trans-ACPD, has been found to be an agonist of mGluRs.
Purity:
≥98% by HPLC
Appearance:
White Solid
Synonyms:
(1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic acid
MSDS:
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InChIKey:
YFYNOWXBIBKGHB-FBCQKBJTSA-N
InChI:
InChI=1S/C7H11NO4/c8-7(6(11)12)2-1-4(3-7)5(9)10/h4H,1-3,8H2,(H,9,10)(H,11,12)/t4-,7+/m1/s1
Canonical SMILES:
C1CC(CC1C(=O)O)(C(=O)O)N
1.Potentiation of NMDA and AMPA responses by group I mGluR in spinal cord motoneurons.
Ugolini A;Corsi M;Bordi F Neuropharmacology. 1997 Aug;36(8):1047-55.
Application of the metabotropic glutamate receptor (mGluR) agonist (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid (1S,3R-ACPD) and the Group I selective mGluR agonist (RS)-3,5-dihydroxyphenylglycine (DHPG) potentiated NMDA- and AMPA-induced potential changes recorded from ventral roots of the isolated hemisected baby rat spinal cord. Potentiation produced by 1S,3R-ACPD was completely abolished by the Group I selective mGluR antagonists (S)-4-carboxyphenylglycine (4CPG) or (+)-alpha-methyl-4-carboxyphenylglycine (MCPG). In addition, the protein kinase C (PKC) blockers staurosporine or chelerythrine chloride were able to antagonize the 1S,3R-ACPD-induced potentiation of both NMDA and AMPA response, suggesting that the enhancing effect induced by Group I mGluRs is modulated by a PKC-mediated mechanism. The mGluRs-induced potentiation of NMDA and AMPA responses may be important in modulating various forms of synaptic plasticity and nociceptive processes.
2.Excitatory amino acid-induced inositol phosphate formation in cultured retinal pigment epithelium.
Fragoso G;López-Colomé AM Vis Neurosci. 1999 Mar-Apr;16(2):263-9.
Excitatory amino acid (EAA)-induced production of inositolphosphates (IPs) was studied in primary cultures of chick retinal pigment epithelium (RPE) following in vitro incorporation of [3H] myo-inositol. Glutamic acid (L-glu) significantly increased [3H]-IPs accumulation (215%). L-glu agonists stimulated [3H]IPs accumulation in the following order of efficiency: N-methyl-D-aspartate (NMDA) > or = L-glu > quisqualate > or = kainate > (IS,3R)-1-aminocyclopentane-1,3-dicarboxylic acid (ACPD). Stimulation was dependent on external Ca2+. The NMDA-induced response was blocked by (+)-5-methyl-10,11-dihydro-5H-dibenzo-cyclohepten-5,10-imine maleate (MK-801) and 3-(2-carboxypiperazin-4-yl)-propyl-1-phosphonic acid (CPP) and was decreased by the L-Ca2+-channel blockers verapamil and nifedipine as well as by dantrolene. The metabotropic glutamate receptor (mGluR) antagonist (+)-alpha-methyl-4-carboxyphenylglycine (+)MCPG inhibited 3,5-dihydroxyphenylglycine (DHPG) and ACPD-induced stimulation, which demonstrates the presence in RPE of mGluRs 1 and/or 5, as well as NMDA receptors coupled directly, or through the influx of external Ca2+, to phospholipase C activation. L-glu agonists showed no effect either on basal level of intracellular cyclic adenosine monophosphate, nor on forskolin- or carbachol-induced stimulation of adenylyl cyclase.
3.Group I mGlu receptor stimulation inhibits activation-induced cell death of human T lymphocytes.
Chiocchetti A;Miglio G;Mesturini R;Varsaldi F;Mocellin M;Orilieri E;Dianzani C;Fantozzi R;Dianzani U;Lombardi G Br J Pharmacol. 2006 Jul;148(6):760-8. Epub 2006 Jun 5.
1. The effects of L-glutamate on activation-induced cell death (AICD) of human activated (1 microg ml(-1) phytohemagglutinin plus 2 U ml(-1) interleukin-2; 8 days) T lymphocytes were studied by measuring anti-CD3 monoclonal antibody (10 microg ml(-1); 18 h)-induced cell apoptosis (Annexin V and propidium iodide staining). 2. L-Glutamate (1 x 10(-8)-1 x 10(-4) M) significantly (P < or = 0.01) inhibited AICD in a concentration-dependent manner (EC50=6.3 x 10(-8) M; maximum inhibition 54.8+/-6.3% at 1 x 10(-6) M). 3. The L-glutamate inhibitory effect was pharmacologically characterized as mediated by group I mGlu receptors, since mGlu receptor agonists reproduced this effect. The EC50 values were: 3.2 x 10(-7) M for (1S,3R)-ACPD; 4.5 x 10(-8) M for quisqualate; 1.0 x 10(-6) M for (S)-3,5-DHPG; 2.0 x 10(-5) M for CHPG. 4. Group I mGlu receptor antagonists inhibited the effects of quisqualate 1.0 x 10(-6) M. The IC50 values calculated were: 8.7 x 10(-5), 4.3 x 10(-6) and 6.3 x 10(-7) M for AIDA, LY 367385 and MPEP, respectively. 5. L-Glutamate (1 x 10(-6) M; 18 h) significantly (P < or = 0.05) inhibited FasL expression (40.8+/-11.3%) (cytofluorimetric analysis), whereas it did not affect Fas signalling.
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CAS 111900-32-4 (1S,3R)-ACPD

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