D-Pyroglutamic acid ethyl ester
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D-Pyroglutamic acid ethyl ester

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Category
Cyclic Amino Acids
Catalog number
BAT-007252
CAS number
68766-96-1
Molecular Formula
C7H11NO3
Molecular Weight
157.17
D-Pyroglutamic acid ethyl ester
IUPAC Name
ethyl (2R)-5-oxopyrrolidine-2-carboxylate
Synonyms
D-Pyr-OEt; (R)-5-Oxopyrrolidine-2-carboxylic acid ethyl ester; D Pyr OEt
Appearance
Pale yellow crystal
Purity
≥ 98% (NMR)
Density
1.161 g/cm3
Melting Point
53-57 °C
Boiling Point
176 °C 12 mmHg(lit.)
Storage
Store at 2-8 °C
InChI
InChI=1S/C7H11NO3/c1-2-11-7(10)5-3-4-6(9)8-5/h5H,2-4H2,1H3,(H,8,9)/t5-/m1/s1
InChI Key
QYJOOVQLTTVTJY-RXMQYKEDSA-N
Canonical SMILES
CCOC(=O)C1CCC(=O)N1
1.Inhibition of trigemino-hypoglossal reflex in rats by oxytocin is mediated by mu and kappa opioid receptors.
Zubrzycka M1, Fichna J, Janecka A. Brain Res. 2005 Feb 21;1035(1):67-72.
Recent studies showed that oxytocin plays an important role in the modulation of pain at different levels of the central nervous system. The present study was undertaken to investigate the effect of oxytocin on trigemino-hypoglossal reflex in rats. With the experimental settings used in this study, we have demonstrated that oxytocin showed significant analgesic effect after intracerebroventricular administration in rats, as assayed by the amplitude of the retractory movements of the tongue after tooth pulp stimulation. Antinociceptive effect of oxytocin was inhibited by subsequent perfusion of cerebral ventricles with oxytocin antagonist, [deamino-Cys1-D-Tyr(OEt)2-Thr4-Orn8]-oxytocin, atosiban. An involvement of opioid system in the oxytocin-induced analgesia was studied after intracerebroventricular administration of different opioid antagonists: non-selective naloxone, mu-selective beta-funaltrexamine, delta-selective naltrindole, and kappa-selective nor-binaltorphimine.
2.Opposite effects of oxytocin on proliferation of osteosarcoma cell lines.
Petersson M1. Regul Pept. 2008 Oct 9;150(1-3):50-4. doi: 10.1016/j.regpep.2008.02.007. Epub 2008 Mar 4.
Oxytocin stimulates proliferation of human osteoblast-like (hOB) cells and human osteosarcoma cells (SaOS-2). In contrast, oxytocin has also been shown to inhibit proliferation of other cell lines such as breast cancer cells. The aim of the present study was to investigate the effects of different concentrations of oxytocin on cell proliferation in osteosarcoma cell lines of different stages of differentiation: SaOS-2, TE-85, and UMR-106. For this purpose cells were incubated with oxytocin (1-1000 pmol/l). Cell proliferation was measured by [(3)H]thymidine incorporation and a commercially available kit (EZ4U). Incubation with oxytocin during 24 h increased proliferation of SaOS-2 cells significantly (100 pmol/l: p<0.01). In contrast, 24 h of incubation with oxytocin decreased proliferation of TE-85 (100 pmol/l: p<0.01) and UMR-106 cells significantly (100 pmol/l: p<0.01). The effects of oxytocin in SaOS-2 and TE-85, but not in UMR-106 cells, were abolished when the cells were incubated with both oxytocin and an oxytocin antagonist (1-deamino-2-D-Tyr-(Oet)-4-Thr-8-Orn-oxytocin).
3.Antinociceptive role of oxytocin in the nucleus raphe magnus of rats, an involvement of mu-opioid receptor.
Wang JW1, Lundeberg T, Yu LC. Regul Pept. 2003 Oct 15;115(3):153-9.
Recent studies showed that oxytocin plays an important role in nociceptive modulation in the central nervous system. The present study was undertaken to investigate the role of oxytocin in antinociception in the nucleus raphe magnus (NRM) of rats and the possible interaction between oxytocin and the opioid systems. Intra-NRM injection of oxytocin induced dose-dependent increases in hindpaw withdrawal latencies (HWLs) to noxious thermal and mechanical stimulation in rats. The antinociceptive effect of oxytocin was significantly attenuated by subsequent intra-NRM injection of the oxytocin antagonist 1-deamino-2-D-Tyr-(Oet)-4-Thr-8-Orn-oxytocin. Intra-NRM injection of naloxone dose-dependently antagonized the increased HWLs induced by preceding intra-NRM injection of oxytocin, indicating an involvement of opioid receptors in oxytocin-induced antinociception in the NRM of rats. Furthermore, the antinociceptive effect of oxytocin was dose-dependently attenuated by subsequent intra-NRM injection of the mu-opioid antagonist beta-funaltrexamine (beta-FNA), but not by the kappa-opioid antagonist nor-binaltorphimine (nor-BNI) or the delta-opioid antagonist naltrindole.
4.Involvement of oxytocin and its receptor in nociceptive modulation in the central nucleus of amygdala of rats.
Han Y1, Yu LC. Neurosci Lett. 2009 Apr 17;454(1):101-4. doi: 10.1016/j.neulet.2009.02.062. Epub 2009 Mar 3.
Studies have demonstrated that oxytocin plays important roles in pain modulation in the central nervous system. Oxytocin-ergic neurons are found in paraventricular nucleus and supraoptic nucleus of the hypothalamus. The oxytocin-ergic neurons send fibers from hypothalamus to amygdala and high density of oxytocin receptors are found in the central nucleus of amygdala (CeA). The present study was performed to investigate the influences of oxytocin and its receptors on nociceptive responses in the CeA of rats. Intra-CeA injection of 0.1, 0.5 or 1nmol of oxytocin induced dose-dependent increases in the handpaw withdrawal latency induced by noxious thermal and mechanical stimulation in rats. The oxytocin-induced anti-nociception could be blocked by the selective oxytocin antagonist 1-deamino-2-d-Tyr-(Oet)-4-Thr-8-Orn-oxytocin. The present study demonstrated that oxytocin and its receptors are involved in nociceptive modulation in the CeA of rats.
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