1. NF-κB
    Metabolic Enzyme/Protease
  2. NF-κB
    Endogenous Metabolite
  3. Cyclo(his-pro)

Cyclo(his-pro) (Synonyms: Cyclo(histidyl-proline); Histidylproline diketopiperazine)

Cat. No.: HY-101402
Handling Instructions

Cyclo(his-pro) (Cyclo(histidyl-proline)) is an orally active cyclic dipeptide structurally related to tyreotropin-releasing hormone. Cyclo(his-pro) could inhibit NF-κB nuclear accumulation. Cyclo(his-pro) can cross the brain-blood-barrier and affect diverse inflammatory and stress responses.

For research use only. We do not sell to patients.

Cyclo(his-pro) Chemical Structure

Cyclo(his-pro) Chemical Structure

CAS No. : 53109-32-3

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Based on 1 publication(s) in Google Scholar

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Description

Cyclo(his-pro) (Cyclo(histidyl-proline)) is an orally active cyclic dipeptide structurally related to tyreotropin-releasing hormone[1]. Cyclo(his-pro) could inhibit NF-κB nuclear accumulation. Cyclo(his-pro) can cross the brain-blood-barrier and affect diverse inflammatory and stress responses[2].

IC50 & Target[1]

NF-κB

 

Human Endogenous Metabolite

 

In Vitro

cyclo(his-pro) (Cyclo(histidyl-proline); 50 μM; 1-48 hours) increases the nuclear level of Nrf2 and inhibits NF-κB nuclear translocation. Cyclo(His-Pro) alone has no effect on nuclear translocation of these transcription factors[2].
cyclo(his-pro) (50 μM; prior to PQ exposure for 48 hours) abolishes protein nitration that followed paraquat (PQ) exposure and lessenes its functional consequences, as shown by decrease in cell apoptosis, detected by caspase 3 activity and by cytochrome c release[2].
Cyclo(his-pro) inhibits NF-κB nuclear accumulation induced by paraquat in rat pheochromocytoma PC12 cells via the Nrf2/heme oxygenase-1 pathway[2].

Western Blot Analysis[1]

Cell Line: PC12 cells
Concentration: 50 μM
Incubation Time: 1, 2, 4, 8, 24, 48 hours
Result: Increased the nuclear level of Nrf2 and inhibited NF-κB nuclear translocation.
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.
Molecular Weight

234.25

Formula

C₁₁H₁₄N₄O₂

CAS No.

53109-32-3

Sequence

Cyclo(His-Pro)

Sequence Shortening

Cyclo(HP)

SMILES

O=C(N[[email protected]]1CC2=CN=CN2)[[email protected]@](CCC3)([H])N3C1=O

Shipping

Room temperature in continental US; may vary elsewhere.

Storage
Powder -80°C 2 years
  -20°C 1 year
In solvent -80°C 6 months
  -20°C 1 month
Solvent & Solubility
In Vitro: 

H2O : ≥ 30 mg/mL (128.07 mM)

*"≥" means soluble, but saturation unknown.

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 4.2689 mL 21.3447 mL 42.6894 mL
5 mM 0.8538 mL 4.2689 mL 8.5379 mL
10 mM 0.4269 mL 2.1345 mL 4.2689 mL
*Please refer to the solubility information to select the appropriate solvent.
References
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Keywords:

Cyclo(his-pro)Cyclo(histidyl-proline)Histidylproline diketopiperazineNF-κBEndogenous MetaboliteNuclear factor-κBNuclear factor-kappaBorallyactivecyclicdipeptidetyreotropin-releasinghormonebrain-blood-barrierinflammatorystressresponsesInhibitorinhibitorinhibit

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Cyclo(his-pro)
Cat. No.:
HY-101402
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