(R)-CPP - CAS 126453-07-4
Category: Inhibitor
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Molecular Formula:
C8H17N2O5P
Molecular Weight:
252.21
COA:
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Targets:
NMDA Receptor
Description:
(R)-CPP, a piperazine derivative, has been found to be an effective NMDA receptor antagonist.
Purity:
≥95% by HPLC
Appearance:
White Solid
Synonyms:
3-((R)-2-Carboxypiperazin-4-yl)-propyl-1-phosphonic acid
MSDS:
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InChIKey:
CUVGUPIVTLGRGI-SSDOTTSWSA-N
InChI:
InChI=1S/C8H17N2O5P/c11-8(12)7-6-10(4-2-9-7)3-1-5-16(13,14)15/h7,9H,1-6H2,(H,11,12)(H2,13,14,15)/t7-/m1/s1
Canonical SMILES:
C1CN(CC(N1)C(=O)O)CCCP(=O)(O)O
1.Long-term potentiation promotes proliferation/survival and neuronal differentiation of neural stem/progenitor cells.
Cho T1, Ryu JK, Taghibiglou C, Ge Y, Chan AW, Liu L, Lu J, McLarnon JG, Wang YT. PLoS One. 2013 Oct 17;8(10):e76860. doi: 10.1371/journal.pone.0076860. eCollection 2013.
Neural stem cell (NSC) replacement therapy is considered a promising cell replacement therapy for various neurodegenerative diseases. However, the low rate of NSC survival and neurogenesis currently limits its clinical potential. Here, we examined if hippocampal long-term potentiation (LTP), one of the most well characterized forms of synaptic plasticity, promotes neurogenesis by facilitating proliferation/survival and neuronal differentiation of NSCs. We found that the induction of hippocampal LTP significantly facilitates proliferation/survival and neuronal differentiation of both endogenous neural progenitor cells (NPCs) and exogenously transplanted NSCs in the hippocampus in rats. These effects were eliminated by preventing LTP induction by pharmacological blockade of the N-methyl-D-aspartate glutamate receptor (NMDAR) via systemic application of the receptor antagonist, 3-[(R)-2-carboxypiperazin-4-yl]-propyl-1-phosphonic acid (CPP).
2.Alterations in synaptic curvature in the dentate gyrus following induction of long-term potentiation, long-term depression, and treatment with the N-methyl-D-aspartate receptor antagonist CPP.
Medvedev NI1, Popov VI, Dallérac G, Davies HA, Laroche S, Kraev IV, Rodriguez Arellano JJ, Doyère V, Stewart MG. Neuroscience. 2010 Dec 1;171(2):390-7. doi: 10.1016/j.neuroscience.2010.09.014. Epub 2010 Sep 17.
Alterations in curvature of the post synaptic density (PSD) and apposition zone (AZ), are believed to play an important role in determining synaptic efficacy. In the present study we have examined curvature of PSDs and AZs 24 h following homosynaptic long-term potentiation (LTP), and heterosynaptic long-term depression (LTD) in vivo, in awake adult rats. High frequency stimulation (HFS) applied to the medial perforant path to the dentate gyrus induced LTP while HFS stimulation of the lateral perforant path induced LTD in the middle molecular layer of the dentate gyrus (DG). Curvature changes were analysed in this area using three dimensional (3-D) reconstructions of electron microscope images of ultrathin serial sections. Very large and significant changes in 3-D measurements of AZ and PSD curvature occurred 24 h following both LTP and LTD, with a flattening of the normal concavity of mushroom spine heads and a change to convexity for thin spines.
3.Hippocampal sharp waves and ripples: Effects of aging and modulation by NMDA receptors and L-type Ca2+ channels.
Kouvaros S1, Kotzadimitriou D1, Papatheodoropoulos C2. Neuroscience. 2015 Jul 9;298:26-41. doi: 10.1016/j.neuroscience.2015.04.012. Epub 2015 Apr 11.
Aging is accompanied by a complicated pattern of changes in the brain organization and often by alterations in specific memory functions. One of the brain activities with important role in the process of memory consolidation is thought to be the hippocampus activity of sharp waves and ripple oscillation (SWRs). Using field recordings from the CA1 area of hippocampal slices we compared SWRs as well as single pyramidal cell activity between adult (3-6-month old) and old (24-34-month old) Wistar rats. The slices from old rats displayed ripple oscillation with a significantly less number of ripples and lower frequency compared with those from adult animals. However, the hippocampus from old rats had significantly higher propensity to organized SWRs in long sequences. Furthermore, the bursts recorded from complex spike cells in slices from old compared with adult rats displayed higher number of spikes and longer mean inter-spike interval. Blockade of N-methyl-D-aspartic acid (NMDA) receptors by 3-((R)-2-carboxypiperazin-4-yl)-propyl-1-phosphonic acid (CPP) increased the amplitude of both sharp waves and ripples and increased the interval between events of SWRs in both age groups.
4.The N-methyl-D-aspartate receptor antagonist CPP alters synapse and spine structure and impairs long-term potentiation and long-term depression induced morphological plasticity in dentate gyrus of the awake rat.
Medvedev NI1, Popov VI, Rodriguez Arellano JJ, Dallérac G, Davies HA, Gabbott PL, Laroche S, Kraev IV, Doyère V, Stewart MG. Neuroscience. 2010 Feb 17;165(4):1170-81. doi: 10.1016/j.neuroscience.2009.11.047. Epub 2009 Dec 1.
Long-term morphological synaptic changes associated with homosynaptic long-term potentiation (LTP) and heterosynaptic long-term depression (LTD) in vivo, in awake adult rats were analyzed using three-dimensional (3-D) reconstructions of electron microscope images of ultrathin serial sections from the molecular layer of the dentate gyrus. For the first time in morphological studies, the specificity of the effects of LTP and LTD on both spine and synapse ultrastructure was determined using an N-methyl-d-aspartate (NMDA) receptor antagonist CPP (3-[(R)-2-carboxypiperazin-4-yl]-propyl-1-phosphonic acid). There were no differences in synaptic density 24 h after LTP or LTD induction, and CPP alone had no effect on synaptic density. LTP increased significantly the proportion of mushroom spines, whereas LTD increased the proportion of thin spines, and both LTP and LTD decreased stubby spine number. Both LTP and LTD increased significantly spine head evaginations (spinules) into synaptic boutons and CPP blocked these changes.
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CAS 126453-07-4 (R)-CPP

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