Cyclic glycine-proline

Cyclic glycine-proline
Clinical data
Other namesCycloprolylglycine; Cyclo-Gly-Pro; Cyclo-Pro-Gly; CGP; Cyclo-GP; Biocovax; Biomedivir; Dexaneurosone; NA-831; NA-81; Nanomedivir; Neurosivir; Traneurocine; (S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Drug classNeuroprotective; Neurogenesis stimulant; Cognitive enhancer
Pharmacokinetic data
Elimination half-life7 hours[1]
Identifiers
IUPAC name
  • (8aS)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC7H10N2O2
Molar mass154.169 g·mol−1
3D model (JSmol)
SMILES
  • C1C[C@H]2C(=O)NCC(=O)N2C1
InChI
  • InChI=1S/C7H10N2O2/c10-6-4-8-7(11)5-2-1-3-9(5)6/h5H,1-4H2,(H,8,11)/t5-/m0/s1
  • Key:OWOHLURDBZHNGG-YFKPBYRVSA-N

Cyclic glycine-proline (cGP) is a small neuroactive peptide that belongs to a group of bioactive 2,5-diketopiperazines (2,5-DKPs) and is also known as cyclo-glycine-proline. cGP is a neutral, stable naturally occurring compound and is endogenous to the human body; found in human plasma, breast milk and cerebrospinal fluid. DKPs are bioactive compounds often found in foods. Cyclic dipeptides such as 2,5 DKPs are formed by the cyclisation of two amino acids of linear peptides produced in heated or fermented foods.[2] The bioactivity of cGP is a property of functional foods and presents in several matrices of foods including blackcurrants.[3]

cGP is metabolite of hormone insulin-like growth factor-1 (IGF-1). It has a cyclic structure, lipophilic nature, and is enzymatically stable which makes its a more favorable candidate for manipulating the binding-release process between IGF-1 and its binding protein thereby, normalizing IGF-1 function.[4]

Under the trade name Traneurocin (developmental code name NA-831), it is being developed as a racetam-like drug for the treatment of COVID-19, Alzheimer's disease, fragile X syndrome, Rett syndrome, major depressive disorder, and other neurological disorders.[5][6][7] In the case of COVID-19, it is specifically being developed for treatment of COVID-19-induced neuropathy.[8]

  1. ^ Cite error: The named reference TranTranVu2018 was invoked but never defined (see the help page).
  2. ^ Otsuka Y, Arita H, Sakaji M, Yamamoto K, Kashiwagi T, Shimamura T, et al. (December 2019). "Investigation of the formation mechanism of proline-containing cyclic dipeptide from the linear peptide". Bioscience, Biotechnology, and Biochemistry. 83 (12): 2355–2363. doi:10.1080/09168451.2019.1659718. PMID 31462170. S2CID 201663846.
  3. ^ Fan D, Alamri Y, Liu K, MacAskill M, Harris P, Brimble M, et al. (June 2018). "Supplementation of Blackcurrant Anthocyanins Increased Cyclic Glycine-Proline in the Cerebrospinal Fluid of Parkinson Patients: Potential Treatment to Improve Insulin-Like Growth Factor-1 Function". Nutrients. 10 (6): 714. doi:10.3390/nu10060714. PMC 6024688. PMID 29865234.
  4. ^ US 7232798, Tran LH, "Neuroprotection and neurogenesis by administering cyclic prolyl glycine", issued 19 June 2007, assigned to NeuroBioMed Corp. 
  5. ^ "Traneurocin". AdisInsight. Springer Nature Switzerland AG. 25 September 2024. Retrieved 19 October 2024.
  6. ^ "Delving into the Latest Updates on Traneurocin with Synapse". Synapse. 19 September 2024. Retrieved 19 October 2024.
  7. ^ Gudasheva TA, Grigoriev VV, Koliasnikova KN, Zamoyski VL, Seredenin SB (November 2016). "Neuropeptide cycloprolylglycine is an endogenous positive modulator of AMPA receptors". Doklady. Biochemistry and Biophysics. 471 (1): 387–389. doi:10.1134/S160767291606003X. PMID 28058675.
  8. ^ Cite error: The named reference ChoiChoiKopp2024 was invoked but never defined (see the help page).
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