Pinealon
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Pinealon

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Pinealon has antioxidant activity and can directly interact with the cell genome.

Category
Others
Catalog number
BAT-009976
CAS number
175175-23-2
Molecular Formula
C15H26N6O8
Molecular Weight
418.40
Pinealon
IUPAC Name
(4S)-4-amino-5-[[(2S)-3-carboxy-1-[[(1S)-1-carboxy-4-(diaminomethylideneamino)butyl]amino]-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
Synonyms
L-Arginine, L-α-glutamyl-L-α-aspartyl-; L-Arginine, N2-(N-L-α-glutamyl-L-α-aspartyl)-; L-α-Glutamyl-L-α-aspartyl-L-arginine; Glu-Asp-Arg peptide; EDR; L-alpha-glutamyl-L-alpha-aspartyl-L-arginine
Related CAS
2703745-42-8 (acetate salt)
Density
1.63±0.1 g/cm3
Sequence
Glu-Asp-Arg
Storage
Store at -20°C
InChI
InChI=1S/C15H26N6O8/c16-7(3-4-10(22)23)12(26)21-9(6-11(24)25)13(27)20-8(14(28)29)2-1-5-19-15(17)18/h7-9H,1-6,16H2,(H,20,27)(H,21,26)(H,22,23)(H,24,25)(H,28,29)(H4,17,18,19)/t7-,8-,9-/m0/s1
InChI Key
QPRZKNOOOBWXSU-CIUDSAMLSA-N
Canonical SMILES
C(CC(C(=O)O)NC(=O)C(CC(=O)O)NC(=O)C(CCC(=O)O)N)CN=C(N)N
1. Pinealon protects the rat offspring from prenatal hyperhomocysteinemia
Alexander Arutjunyan, Lyudmila Kozina, Sergey Stvolinskiy, Yelena Bulygina, Anna Mashkina, Vladimir Khavinson Int J Clin Exp Med. 2012;5(2):179-85. Epub 2012 Apr 6.
The offspring of rats with experimental hyperhomocysteinemia caused by alimentary loading with dietary methionine within pregnancy has been studied. Using pinealon (Glu-Asp-Arg) under these conditions was found to result in the offspring cognitive function being improved significantly and their cerebellum neurons becoming more resistant to oxidative stress. This may be proved by the fact that the administration of pinealon to pregnant rats loaded with methionine improved their offspring spatial orientation and learning ability and decreased both reactive oxygen species accumulation and the number of necrotic cells in the population of the neurons isolated from the cerebellum of the offspring developed under the prenatal hyperhomocysteinemia. Our experiments allowed confirming the neuroprotective properties of pinealon, which is in agreement with the previous data obtained by us in vitro.
2. Pinealon increases cell viability by suppression of free radical levels and activating proliferative processes
V Khavinson, Y Ribakova, K Kulebiakin, E Vladychenskaya, L Kozina, A Arutjunyan, A Boldyrev Rejuvenation Res. 2011 Oct;14(5):535-41. doi: 10.1089/rej.2011.1172. Epub 2011 Oct 6.
The synthetic tripeptide pinealon (Glu-Asp-Arg) demonstrates dose-dependent restriction of reactive oxygen species (ROS) accumulation in cerebellar granule cells, neutrophils, and pheochromocytoma (PC12) cells, induced by oxidative stress stimulated by receptor-dependent or -independent processes. At the same time, pinealon decreases necrotic cell death measured by the propidium iodide test. The protective effect of pinealon is accompanied with a delayed time course of ERK 1/2 activation and modification of the cell cycle. Because restriction of ROS accumulation and cell mortality is saturated at lower concentrations, whereas cell cycle modulation continues at higher concentrations of pinealon, one can conclude that besides its known antioxidant activity, pinealon is able to interact directly with the cell genome.
3. [Pinealon and Cortexin influence on behavior and neurochemical processes in 18-month aged rats within hypoxia and hypothermia]
A M Mendzheritsky, G V Karantysh, G A Ryzhak, V N Prokofiev Adv Gerontol. 2015;28(3):532-539.
The research of Cortexin and Pinealon within two models of stress, acute hypobaric hypoxia and mild hypothermia, within 18-month aged rats has been held. The peculiarities of peptide preparations' influence on behavior and neurochemical indeces have been identified. Cortexin shows a more pronounced effect on free radical processes and caspase 3 activity in brain than Pinealon. Both preparations forward an accumulation of adrenergic mediator within rats' brains in the model of acute hypobaric hypoxia, as well as serotonin within cerebrum cortex in the model of mild hypothermia, which may underlie their geroprotective effects.
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