| Identification | Back Directory | [Name]
CYCLO(-HIS-PRO) | [CAS]
53109-32-3 | [Synonyms]
HIS-PRO, CYCLIC
CYCLO(-HIS-PRO)
Cyclo-Pro-His-HO
CYCLO(HIS-PRO), >99%
Cyclo(histidyl-proline)
Protirelin EP Impurity E
Cyclo(L-histidyl-L-proline)
histidylproline dioxopiperazine
Histidylproline diketopiperazine
CYCLO(HISTIDYL-PROLINE); HISTIDYLPROLINE DIKETOPIPERAZINE
(3S,6S)-3-(3H-imidazol-4-ylmethyl)-1,4-diazabicyclo[4.4.0]decane-2,5-dione
Cyclo(his-pro),Cyclo(histidyl-proline),Histidylproline diketopiperazine, >99%
3-(1H-imidazol-5-ylmethyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(1H-imidazol-4-ylmethyl)-, (3S,8aS)- | [Molecular Formula]
C11H14N4O2 | [MDL Number]
MFCD00133207 | [MOL File]
53109-32-3.mol | [Molecular Weight]
234.25 |
| Chemical Properties | Back Directory | [Melting point ]
162-164 °C | [Boiling point ]
659.3±48.0 °C(Predicted) | [density ]
1.41±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
DMF: 1 mg/ml; DMSO: 1 mg/ml; Ethanol: 1 mg/ml; PBS (pH 7.2): 1 mg/ml | [form ]
A neat oil | [pka]
12.73±0.40(Predicted) | [color ]
Light yellow to yellow | [Cosmetics Ingredients Functions]
HUMECTANT
ANTIOXIDANT
SKIN CONDITIONING - MISCELLANEOUS
PRESERVATIVE
SKIN PROTECTING | [InChI]
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 | [InChIKey]
NAKUGCPAQTUSBE-IUCAKERBSA-N | [SMILES]
[C@@]12([H])CCCN1C(=O)[C@H](CC1=CNC=N1)NC2=O |
| Hazard Information | Back Directory | [Uses]
Cyclo(L-histidyl-L-proline) is used in the pharmaceutical composition comprising cyclo(His-Pro) for preventing or treating obesity. | [Definition]
ChEBI: Cyclo(L-His-L-Pro) is a homodetic cyclic peptide resulting from the formal condensation of both the amino and acid groups of L-histidine with the acid and amino groups of L-proline. It is a metabolite of thyrotropin-releasing hormone (TRH). It has a role as a human blood serum metabolite, a dopamine uptake inhibitor and an anti-inflammatory agent. It is a homodetic cyclic peptide, a dipeptide, a pyrrolopyrazine and a member of imidazoles. It is functionally related to a L-histidine and a L-proline. | [in vivo]
Cyclo(his-pro) (Cyclo(histidyl-proline); 1.8 mg/ear; topical application on the right ear; 30 min prior to TPA) reduces TPA-induced ear oedema confirming that it can exert anti-inflammatory effect[2].
Cyclo(his-pro) exerts in vivo anti-inflammatory effects in the central nervous system by down-regulating hepatic and cerebral TNFα expression thereby counteracting LPS-induced gliosis. Moreover, by up-regulating Bip, Cyclo(his-pro) increases the ER stress sensitivity andtriggers the unfolded protein response to alleviate the ER stress[3].
| Animal Model: | Sixty two/three month-old male C57BL/6 mice (25-30 g)[2] | | Dosage: | 1.8 mg/ear | | Administration: | Topical application on the right ear; 30 min prior to TPA | | Result: | Reduced TPA-induced ear oedema.
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| [IC 50]
NF-κB; Human Endogenous Metabolite |
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