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| Targets |
Cyclo(his-pro) targets multiple pathways. It is a metabolite of thyrotropin-releasing hormone. It acts as a dopamine uptake inhibitor and anti-inflammatory agent. It shields against oxidative damage by activating Nrf2. It can affect diverse inflammatory and stress responses.
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| ln Vitro |
cyclo(his-pro) (Cyclo(histidyl-proline); 50 μM; 1-48 hours) raises nuclear levels of Nrf2 and inhibits NF-κB nuclear translocation. Cyclo(His-Pro) alone has little effect on the nuclear translocation of these transcription factors [2]. cyclo(his-pro) (50 μM; 48 hours before PQ exposure) removes protein nitration following paraquat (PQ) exposure and mitigates its functional implications as determined by caspase 3 activity and cytochromes in cells Reduced apoptosis as indicated in version c [2]. Cyclo (his-pro) suppresses paraquat-induced nuclear accumulation of NF-κB in rat pheochromocytoma PC12 cells through the Nrf2/heme oxygenase-1 pathway [2].
Cyclo(his-pro) is a dopamine uptake inhibitor and anti-inflammatory agent. It shields against oxidative damage by activating Nrf2. It has various biological effects in the CNS, as well as endocrine effects. It can affect diverse inflammatory and stress responses. |
| ln Vivo |
Applying Cyclo(his-pro) (Cyclo(histidyl proline) topically to the right ear 30 minutes before to TPA exposure will lessen TPA-induced otitis media, indicating that it has anti-inflammatory properties [2]. Cyclo(his-pro) inhibits LPS-induced gliosis by downregulating TNFα expression in the liver and brain, which has anti-inflammatory effects in vivo on the central nervous system. Furthermore, by upregulating Bip, raising ER stress sensitivity, and inducing the unfolded protein response, Cyclo (his-pro) reduces ER stress [3].
Cyclo(his-pro) is orally active and can cross the blood-brain barrier. It has been shown to have effects on neuroinflammation-based degenerative conditions through both oral and parenteral administration routes. It is a metabolite of thyrotropin-releasing hormone. |
| Enzyme Assay |
Cyclo(his-pro) is evaluated in cell-free assays for its ability to activate Nrf2. The compound is incubated with Nrf2 and a reporter system, and the activation of Nrf2 is measured. Its antioxidant activity can be assessed using biochemical assays.
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| Cell Assay |
Western Blot analysis [1]
Cell Types: PC12 cells Tested Concentrations: 50 μM Incubation Duration: 1, 2, 4, 8, 24, 48 hrs (hours) Experimental Results: Nrf2 nuclear levels increased and NF-κB nuclear translocation was inhibited. Cyclo(his-pro) is assessed in cell-based assays to study its effects on dopamine uptake, inflammation, and oxidative stress. Cells are treated with Cyclo(his-pro), and dopamine uptake, inflammatory markers, and oxidative stress markers are measured. |
| Animal Protocol |
Animal/Disease Models: Sixty-two/three-month-old male C57BL/6 mice (25-30 g) [2]
Doses: 1.8 mg/ear Route of Administration: Apply topically to the right ear; 30 minutes before TPA Experimental Results: TPA Reduce ear edema caused. Cyclo(his-pro) is administered orally or parenterally in animal models to evaluate its effects on neuroinflammation and degenerative conditions. It has been shown to have effects on neuroinflammation-based degenerative conditions. |
| ADME/Pharmacokinetics |
Cyclo(his-pro) is orally active and can cross the blood-brain barrier. It has a molecular weight of 234.25 and a molecular formula of C11H14N4O2. It has a CAS number of 53109-32-3. The compound is a cyclic dipeptide.
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| Toxicity/Toxicokinetics |
No detailed toxicity data is available for Cyclo(his-pro). The compound is for research use only and is not intended for human therapeutic use. It is a naturally occurring compound and is generally considered safe for research purposes.
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| References | |
| Additional Infomation |
cyclic peptide (L-histidine-L-proline) is a homocyclic peptide formed by the condensation of the amino and carboxyl groups of L-histidine with the carboxyl and amino groups of L-proline. It is a metabolite of thyrotropin-releasing hormone (TRH). It is a human serum metabolite with dopamine uptake inhibitor and anti-inflammatory effects. It is a homocyclic peptide, dipeptide, pyrrolopyrazine compound, belonging to the imidazole class of compounds. Its function is related to L-histidine and L-proline.
Cyclo(his-pro) is a naturally occurring cyclic dipeptide. It has a CAS number of 53109-32-3. It is a metabolite of thyrotropin-releasing hormone. It is used in research to study neuroinflammation, oxidative stress, and dopamine uptake. It is not approved for clinical use. |
| Molecular Formula |
C11H14N4O2
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|---|---|
| Molecular Weight |
234.259
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| Exact Mass |
234.112
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| CAS # |
53109-32-3
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| Related CAS # |
Cyclo(his-pro) TFA;936749-56-3
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| PubChem CID |
449094
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.36g/cm3
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| Boiling Point |
650.3ºC at 760mmHg
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| Flash Point |
347.1ºC
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| LogP |
-0.4
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
17
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| Complexity |
346
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| Defined Atom Stereocenter Count |
2
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| SMILES |
C1C[C@H]2C(=O)N[C@H](C(=O)N2C1)CC3=CN=CN3
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| InChi Key |
NAKUGCPAQTUSBE-IUCAKERBSA-N
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| 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
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| Chemical Name |
(3S,8aS)-3-(1H-imidazol-5-ylmethyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
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| Synonyms |
Cyclo(-His-Pro); Cyclo(his-pro)
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O : ≥ 30 mg/mL (~128.07 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.2688 mL | 21.3438 mL | 42.6876 mL | |
| 5 mM | 0.8538 mL | 4.2688 mL | 8.5375 mL | |
| 10 mM | 0.4269 mL | 2.1344 mL | 4.2688 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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