Cat. No.: HY-101402

Cyclo(his-pro)

(Synonyms: Cyclohistidyl-proline; Histidylproline diketopiperazine)

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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.

Purity: 98.95%
CAS No.: 53109-32-3
Formula: C₁₁H₁₄N₄O₂
Molecular Weight:234.25

Storage:

Pure form -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month

Cyclo(his-pro) Chemical Structure

CAS No.: 53109-32-3

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Fluorescent Dye

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biological Activity
- Description
- IC₅₀ & Target
- In Vitro
- In Vivo
Chemical Information
Solvent & Solubility
- In Vitro
Purity & Documentation
References
Help & FAQs
Classifications
Bioz

Biological Activity

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

All NF-κB Isoforms :

All Endogenous Metabolite Isoforms :

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].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

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].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

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.

Chemical Information

CAS No. 53109-32-3
Appearance Solid-Liquid Mixture
Molecular Weight 234.25
Formula C₁₁H₁₄N₄O₂
Color Colorless to off-white
SMILES

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

Cyclohistidyl-proline; Histidylproline diketopiperazine
Sequence Shortening

Cyclo(HP)
Structure Classification
- Others
Initial Source
- Endogenous metabolite
Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Pure form	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Solvent & Solubility

In Vitro:

DMSO : 50 mg/mL (213.45 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

H₂O : ≥ 30 mg/mL (128.07 mM)

* "≥" means soluble, but saturation unknown.

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

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. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

Molarity Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

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Purity & Documentation

Select Batch:

Purity: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (278 KB)
SDS (396 KB)
- English - EN (396 KB)
- Français - FR (396 KB)
- Deutsch - DE (396 KB)
- Norwegian - NO (396 KB)
- Español - ES (396 KB)
- Swedish - SV (396 KB)
- Italian - IT (396 KB)
- Korean - KR (396 KB)
- Portuguese - PT (396 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

References

[1]. Grottelli S, et al. The Role of Cyclo(His-Pro) in Neurodegeneration. Int J Mol Sci. 2016 Aug 12;17(8). pii: E1332. [Content Brief]

[2]. Minelli A, et al. 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. [Content Brief]

[3]. Bellezza I, et al. 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. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
H₂O / DMSO	1 mM	4.2689 mL	21.3447 mL	42.6894 mL	106.7236 mL
	5 mM	0.8538 mL	4.2689 mL	8.5379 mL	21.3447 mL
	10 mM	0.4269 mL	2.1345 mL	4.2689 mL	10.6724 mL
	15 mM	0.2846 mL	1.4230 mL	2.8460 mL	7.1149 mL
	20 mM	0.2134 mL	1.0672 mL	2.1345 mL	5.3362 mL
	25 mM	0.1708 mL	0.8538 mL	1.7076 mL	4.2689 mL
	30 mM	0.1423 mL	0.7115 mL	1.4230 mL	3.5575 mL
	40 mM	0.1067 mL	0.5336 mL	1.0672 mL	2.6681 mL
	50 mM	0.0854 mL	0.4269 mL	0.8538 mL	2.1345 mL
	60 mM	0.0711 mL	0.3557 mL	0.7115 mL	1.7787 mL
	80 mM	0.0534 mL	0.2668 mL	0.5336 mL	1.3340 mL
	100 mM	0.0427 mL	0.2134 mL	0.4269 mL	1.0672 mL

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

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Cyclo(his-pro)

Immunology/Inflammation Compound Library

Metabolism/Protease Compound Library

NF-κB Signaling Compound Library

Stem Cell Signaling Compound Library

Natural Product Library

CNS-Penetrant Compound Library

Human Endogenous Metabolite Compound Library

Anti-Aging Compound Library

Antioxidant Compound Library

Oxygen Sensing Compound Library

Endoplasmic Reticulum Stress Compound Library

Pyroptosis Compound Library

Orally Active Compound Library

Anti-Pancreatic Cancer Compound Library

Anti-Cancer Metabolism Compound Library

Transcription Factor-Targeted Library

Food-Sourced Compound Library

Peptide Library

Cyclic Peptide Library

Human Metabolite Library

Heterocyclic Compound Library

Pain-Related Compound Library

Animal-Sourced Natural Product Library

Multi-Target Compound Library

Radioprotector Library

Bioactive Compound Library Max

MCE Bioactive Compound Library

Natural Product Library Plus

Peptide Compound Library

Natural Product and Natural Product-Like Compound Library

Bioactive Compound Library

Non-Alcoholic Fatty Liver Disease (NAFLD) Compound Library

RO5 Drug-like Natural Product Library

Cell Proliferation Compound Library

High-Throughput Bioactive Compound Library

High-Throughput Natural Product Library

Mass Spectrometry Human Endogenous Metabolite Library

Mass Spectrometry Human Metabolite Library

Natural Product Diversity Scaffold Library

Lactylation Compound Library

Mass Spectrometry Natural Product Library

All NF-κB Isoforms

All Endogenous Metabolite Isoforms

Biological Activity

Chemical Information

Solvent & Solubility

Purity & Documentation

References

Help & FAQs

Complete Stock Solution Preparation Table

Cyclo(his-pro) Related Classifications

Cat. No.: HY-101402