Cyclo(his-pro)
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MedKoo CAT#: 526906

CAS#: 53109-32-3

Description: Cyclo(his-pro) is a cyclic dipeptide derived from the hydrolytic removal of the amino-terminal pyroglutamic acid residue of the hypothalamic thyrotropin-releasing hormone, may be important in regulating the nature of the glial cell contribution. Cyclo(His-Pro) is ubiquitous in the central nervous system and is a key substrate of organic cation transporters, which are strongly linked to neuroprotection. Cyclo(His-Pro) has striking potential for therapeutic application by both parenteral and oral administration routes and may represent an important new tool in counteracting neuroinflammation-based degenerative pathologies.

Chemical Structure

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Cyclo(his-pro)
CAS# 53109-32-3
Instruction

Theoretical Analysis

MedKoo Cat#: 526906
Name: Cyclo(his-pro)
CAS#: 53109-32-3
Chemical Formula: C11H14N4O2
Exact Mass: 234.11
Molecular Weight: 234.259
Elemental Analysis: C, 56.40; H, 6.02; N, 23.92; O, 13.66

Price and Availability

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25mg USD 295
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Synonym: Cyclo(his-pro); Cyclo(-His-Pro).

IUPAC/Chemical Name: (3S,8aS)-3-((1H-imidazol-4-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

InChi Key: NAKUGCPAQTUSBE-IUCAKERBSA-N

InChi Code: InChI=1S/C11H14N4O2/c16-10-9-2-1-3-15(9)11(17)8(14-10)4-7-5-12-6-13-7/h5-6,8-9H,1-4H2,(H,12,13)(H,14,16)/t8-,9-/m0/s1

SMILES Code: O=C(N[C@H]1CC2=CNC=N2)[C@@](CCC3)([H])N3C1=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 234.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Kastin AJ, Pan W. Involvement of the Blood-Brain Barrier in Metabolic Regulation. CNS Neurol Disord Drug Targets. 2016 Sep 20. [Epub ahead of print] PubMed PMID: 27658512.

2: Grottelli S, Ferrari I, Pietrini G, Peirce MJ, Minelli A, Bellezza I. The Role of Cyclo(His-Pro) in Neurodegeneration. Int J Mol Sci. 2016 Aug 12;17(8). pii: E1332. doi: 10.3390/ijms17081332. Review. PubMed PMID: 27529240; PubMed Central PMCID: PMC5000729.

3: Jung EY, Hong YH, Park C, Suh HJ. Effects of Cyclo-His-Pro-enriched yeast hydrolysate on blood glucose levels and lipid metabolism in obese diabetic ob/ob mice. Nutr Res Pract. 2016 Apr;10(2):154-60. doi: 10.4162/nrp.2016.10.2.154. Epub 2015 Dec 24. PubMed PMID: 27087898; PubMed Central PMCID: PMC4819125.

4: Lee HJ, Son HS, Park C, Suh HJ. Preparation of Yeast Hydrolysate Enriched in Cyclo-His-Pro (CHP) by Enzymatic Hydrolysis and Evaluation of Its Functionality. Prev Nutr Food Sci. 2015 Dec;20(4):284-91. doi: 10.3746/pnf.2015.20.4.284. Epub 2015 Dec 31. PubMed PMID: 26770916; PubMed Central PMCID: PMC4700918.

5: Prasad C, Imrhan V, Juma S, Maziarz M, Prasad A, Tiernan C, Vijayagopal P. Bioactive Plant Metabolites in the Management of Non-Communicable Metabolic Diseases: Looking at Opportunities beyond the Horizon. Metabolites. 2015 Dec 12;5(4):733-65. doi: 10.3390/metabo5040733. Review. PubMed PMID: 26703752; PubMed Central PMCID: PMC4693193.

6: Bellezza I, Grottelli S, Mierla AL, Cacciatore I, Fornasari E, Roscini L, Cardinali G, Minelli A. Neuroinflammation and endoplasmic reticulum stress are coregulated by cyclo(His-Pro) to prevent LPS neurotoxicity. Int J Biochem Cell Biol. 2014 Jun;51:159-69. doi: 10.1016/j.biocel.2014.03.023. Epub 2014 Mar 31. PubMed PMID: 24699213.

7: Brunetti L, Chiavaroli A, Cocco A, Ferrante C, Ferrucci A, Luisi G, Orlando G, Pinnen F, Vacca M. Synthesis and neuromodulatory effects of TRH-related peptides: inhibitory activity on catecholamine release in vitro. Pharmacol Rep. 2013;65(4):823-35. PubMed PMID: 24145076.

8: Choi SA, Yun JW, Park HS, Choi JW. Hypoglycemic dipeptide cyclo (His-Pro) significantly altered plasma proteome in streptozocin-induced diabetic rats and genetically-diabetic (ob/ob) mice. Mol Biol Rep. 2013 Feb;40(2):1753-65. doi: 10.1007/s11033-012-2229-0. Epub 2012 Oct 20. PubMed PMID: 23086277.

9: Choi SA, Suh HJ, Yun JW, Choi JW. Differential gene expression in pancreatic tissues of streptozocin-induced diabetic rats and genetically-diabetic mice in response to hypoglycemic dipeptide cyclo (His-Pro) treatment. Mol Biol Rep. 2012 Sep;39(9):8821-35. doi: 10.1007/s11033-012-1746-1. Epub 2012 Jun 17. PubMed PMID: 22707198.

10: Park SW, Choi SA, Yun JW, Choi JW. Alterations in pancreatic protein expression in STZ-induced diabetic rats and genetically diabetic mice in response to treatment with hypoglycemic dipeptide Cyclo (His-Pro). Cell Physiol Biochem. 2012;29(3-4):603-16. PubMed PMID: 22616141.

11: Minelli A, Grottelli S, Mierla A, Pinnen F, Cacciatore I, Bellezza I. Cyclo(His-Pro) exerts anti-inflammatory effects by modulating NF-κB and Nrf2 signalling. Int J Biochem Cell Biol. 2012 Mar;44(3):525-35. doi: 10.1016/j.biocel.2011.12.006. Epub 2011 Dec 14. PubMed PMID: 22185821.

12: Jung EY, Lee HS, Choi JW, Ra KS, Kim MR, Suh HJ. Glucose tolerance and antioxidant activity of spent brewer's yeast hydrolysate with a high content of Cyclo-His-Pro (CHP). J Food Sci. 2011 Mar;76(2):C272-8. doi: 10.1111/j.1750-3841.2010.01997.x. Epub 2011 Feb 1. PubMed PMID: 21535746.

13: Koo KB, Suh HJ, Ra KS, Choi JW. Protective effect of cyclo(his-pro) on streptozotocin-induced cytotoxicity and apoptosis in vitro. J Microbiol Biotechnol. 2011 Feb;21(2):218-27. PubMed PMID: 21364307.

14: Minelli A, Conte C, Grottelli S, Bellezza I, Emiliani C, Bolaños JP. Cyclo(His-Pro) up-regulates heme oxygenase 1 via activation of Nrf2-ARE signalling. J Neurochem. 2009 Nov;111(4):956-66. doi: 10.1111/j.1471-4159.2009.06376.x. Epub 2009 Sep 7. Erratum in: J Neurochem. 2014 Mar;128(6):975. PubMed PMID: 19735445.

15: Wainwright CL, McGrath JC. Themed section: Advances in nutritional pharmacology. Editorial. Br J Pharmacol. 2009 Sep;158(2):393-4. doi: 10.1111/j.1476-5381.2009.00457.x. PubMed PMID: 19732059; PubMed Central PMCID: PMC2757679.

16: Abiram A, Kolandaivel P. Structural analysis and the effect of cyclo(His-Pro) dipeptide on neurotoxins--a dynamics and density functional theory study. J Mol Model. 2010 Feb;16(2):193-202. doi: 10.1007/s00894-009-0531-0. Epub 2009 Jun 25. PubMed PMID: 19554355.

17: Song MK, Rosenthal MJ, Song AM, Uyemura K, Yang H, Ament ME, Yamaguchi DT, Cornford EM. Body weight reduction in rats by oral treatment with zinc plus cyclo-(His-Pro). Br J Pharmacol. 2009 Sep;158(2):442-50. doi: 10.1111/j.1476-5381.2009.00201.x. Epub 2009 May 5. PubMed PMID: 19422374; PubMed Central PMCID: PMC2757683.

18: Minelli A, Conte C, Grottelli S, Bellezza I, Cacciatore I, Bolaños JP. Cyclo(His-Pro) promotes cytoprotection by activating Nrf2-mediated up-regulation of antioxidant defence. J Cell Mol Med. 2009 Jun;13(6):1149-61. doi: 10.1111/j.1582-4934.2008.00326.x. Epub 2008 Mar 29. PubMed PMID: 18373731; PubMed Central PMCID: PMC4496110.

19: Minelli A, Bellezza I, Grottelli S, Galli F. Focus on cyclo(His-Pro): history and perspectives as antioxidant peptide. Amino Acids. 2008 Aug;35(2):283-9. Epub 2007 Dec 28. Review. PubMed PMID: 18163175.

20: Taubert D, Grimberg G, Stenzel W, Schömig E. Identification of the endogenous key substrates of the human organic cation transporter OCT2 and their implication in function of dopaminergic neurons. PLoS One. 2007 Apr 25;2(4):e385. PubMed PMID: 17460754; PubMed Central PMCID: PMC1851987.