ChemicalBook--->CAS DataBase List--->32302-76-4

32302-76-4

32302-76-4 Structure

32302-76-4 Structure
IdentificationBack Directory
[Name]

glycyl-prolyl-glutamic acid
[CAS]

32302-76-4
[Synonyms]

SC-252859
Glypromate
Gly-Pro-Glu >=98% (HPLC)
glycyl-prolyl-glutamic acid
Glycyl-L-prolyl-L-glutamic acid
L-GlutaMic acid, glycyl-L-prolyl-
glycyl-prolyl-glutamic acid USP/EP/BP
[Molecular Formula]

C12H19N3O6
[MDL Number]

MFCD00677175
[MOL File]

32302-76-4.mol
[Molecular Weight]

301.3
Chemical PropertiesBack Directory
[Boiling point ]

675.7±55.0 °C(Predicted)
[density ]

1.431±0.06 g/cm3(Predicted)
[storage temp. ]

Store at 0°C
[solubility ]

H2O: >5mg/mL
[form ]

white powder
[pka]

3.51±0.10(Predicted)
[color ]

White to off-white
[InChI]

1S/C12H19N3O6/c13-6-9(16)15-5-1-2-8(15)11(19)14-7(12(20)21)3-4-10(17)18/h7-8H,1-6,13H2,(H,14,19)(H,17,18)(H,20,21)/t7-,8-/m0/s1
[InChIKey]

JJGBXTYGTKWGAT-YUMQZZPRSA-N
[SMILES]

NCC(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(O)=O)C(O)=O
Safety DataBack Directory
[WGK Germany ]

3
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Uses]

Gly-Pro-Glu is a neuroactive peptide with a potent action on acetylcholine release. Gly-Pro-Glu is the N-terminal tripeptide of insulin-like growth factor-I. Gly-Pro-Glu inhibits glutamate binds to N-methyl-D-aspartate (NMDA) receptor with an IC50 value of 14.7 μM. Gly-Pro-Glu can be used for the research of neuroprotection [1][2].
[Definition]

ChEBI: Gly-Pro-Glu is an oligopeptide.
[Biological Activity]

Gly-Pro-Glu (GPE) is a neuroactive peptide and prevents the binding of glutamate to N-methyl-D-aspartate (NMDA) receptor. It positively regulates the potassium-mediated release of acetylcholine from r at cortical slices. Thusit is involved in the control of brain function. In vitro studies show th at this peptide confers neuroprotection to CA1-2 hippocampal neurons against excitotoxic insult.''Gly-Pro-Glu is a neuroprotective compound and the N-terminal tripeptide of IGF-1. Gly-Pro-Glu is neuroprotective after central administration in animal models of neurodegenerative processessuch as Huntington′sParkinson′sAlzheimer′s diseasesand varies acute brain injury animal models. The neuroprotective activity is not related to its affinity to glutamate receptor. Findings indicate th at GPE mimics insulin-like growth factor I effects on the somatostatin system through a mechanism independen
[in vivo]

Gly-Pro-Glu (300 mg; i.p. once per day; on day 0, 6 and 12) shows an in vivo effect protecting the temporal cortical somatostatinergic system from Abeta insult.[2].

Animal Model:Ovariectomized rats with Abeta25-35 injection[2]
Dosage:300 mg
Administration:Intraperitoneal injection; 300 mg per day; on day 0, 6 and 12
Result:Recovered Abeta25-35-induced the reduction of somatostatin (SRIF) content and SRIF receptor density, and reduced the inhibitory effect of SRIF on adenylyl cyclase activity.
[References]

[1] Sara VR, et al. Identification of Gly-Pro-Glu (GPE), the aminoterminal tripeptide of insulin-like growth factor 1 which is truncated in brain, as a novel neuroactive peptide. Biochem Biophys Res Commun. 1989 Dec 15;165(2):766-71. DOI:10.1016/s0006-291x(89)80032-4
[2] Aguado-Llera D, et al. Gly-Pro-Glu protects beta-amyloid-induced somatostatin depletion in the rat cortex. Neuroreport. 2004 Aug 26;15(12):1979-82. DOI:10.1097/00001756-200408260-00029
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