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| Other Sizes |
| Targets |
Cyclo-(Pro-Gly) targets multiple biological pathways. It inhibits chitinase B activity and exhibits weak antibacterial properties. The compound acts as a quorum-sensing molecule in microbial communication, influencing bacterial population behavior. In the central nervous system, Cyclo-(Pro-Gly) appears to facilitate memory and may be involved in a novel memory regulatory mechanism, as suggested by its presence in rat brain. The compound also demonstrates neuroprotective activities, potentially through modulation of neurotransmitter systems or reduction of oxidative stress.
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| ln Vitro |
In vitro studies demonstrate that Cyclo-(Pro-Gly) exhibits weak antibacterial activity with a minimum inhibitory concentration (MIC) of 0.8 g/L against Bacillus subtilis. The compound shows antioxidant properties through free radical scavenging activity and inhibits chitinase B enzymatic activity. Cyclo-(Pro-Gly) possesses antialgal activity against common harmful red tide microalgae. Cytotoxicity has been observed at concentrations of 10 μmol/L. The compound's multifunctional nature makes it valuable in chemistry, microbiology, and neurological research.
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| ln Vivo |
Cyclo-(Pro-Gly) (0.1 and 10 mg/kg, ip) appears to be a chemical that facilitates memory, and its presence in the rat brain indicates the possibility of a novel memory regulatory mechanism[3].
In vivo studies in rats demonstrate that Cyclo-(Pro-Gly) administered intraperitoneally at doses of 0.1 and 10 mg/kg appears to facilitate memory. The compound's presence in rat brain suggests the possibility of a novel endogenous memory regulatory mechanism. Cyclo-(Pro-Gly) exhibits anti-amnestic effects and neuroprotective actions in animal models. The compound has been identified as an endogenous cyclic dipeptide in rat brain, indicating potential physiological roles in cognition and memory processes. Further in vivo studies are warranted to explore its therapeutic potential in neurodegenerative and cognitive disorders. |
| Enzyme Assay |
In vitro enzyme/receptor binding assays for Cyclo-(Pro-Gly) typically involve chitinase B inhibition assays using fluorogenic substrates. Enzyme activity is measured by the release of fluorescent product upon substrate cleavage, with inhibition calculated as percentage decrease in fluorescence compared to control. For antibacterial activity assessment, broth microdilution methods are used to determine minimum inhibitory concentration (MIC) against bacterial strains such as Bacillus subtilis. Antioxidant activity is evaluated using DPPH or ABTS radical scavenging assays, measuring the compound's ability to neutralize free radicals.
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| Cell Assay |
In vitro cellular assays for Cyclo-(Pro-Gly) typically employ various cell lines to assess its biological activities. Cytotoxicity is evaluated using standard cell viability assays such as MTT or CCK-8 in relevant cell lines, with observed cytotoxicity at 10 μmol/L. For neuroprotective studies, neuronal cell cultures are treated with the compound prior to or concurrently with neurotoxic insults, and cell survival is assessed. Antimicrobial activity is evaluated in bacterial culture systems using disc diffusion or broth microdilution methods. The compound's antioxidant effects are assessed in cellular models of oxidative stress.
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| Animal Protocol |
In vivo animal experiments for Cyclo-(Pro-Gly) typically utilize rodent models. The compound is administered intraperitoneally at doses of 0.1 and 10 mg/kg. Memory-enhancing effects are evaluated using behavioral paradigms such as passive avoidance tests or Morris water maze. The compound's presence in rat brain is confirmed through brain tissue analysis following administration. Neuroprotective effects are assessed in models of neurodegeneration or cognitive impairment. Dosing regimens and administration routes are optimized based on the specific experimental endpoints and animal species used.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of Cyclo-(Pro-Gly) are characteristic of small cyclic dipeptides. With a molecular weight of 154.17 g/mol, the compound is expected to have favorable oral absorption and blood-brain barrier penetration. Its presence in rat brain following intraperitoneal administration confirms central nervous system bioavailability. The compound is soluble in DMSO and may dissolve in water, ethanol, or DMF. Storage conditions: powder at -20°C for 3 years or 4°C for 2 years; in solvent at -80°C for 6 months or -20°C for 1 month.
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| Toxicity/Toxicokinetics |
The toxicological profile of Cyclo-(Pro-Gly) is generally favorable given its status as a naturally occurring compound found in green algae and present endogenously in rat brain. Cytotoxicity has been observed at concentrations of 10 μmol/L, suggesting a concentration-dependent safety margin. As a diketopiperazine commonly found in foods and biological systems, the compound is expected to have low acute toxicity. Standard toxicological evaluations including repeated-dose toxicity, genotoxicity, and reproductive toxicity studies would be required for therapeutic development, though such comprehensive data are not extensively published for this specific compound.
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| References |
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| Additional Infomation |
Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione is an organic nitrogen and organic oxygen compound whose function is related to α-amino acids. It has been reported that hexahydropyrrolo[1,2-a]pyrazine-1,4-dione exists in Streptomyces nigra, Streptomyces antioxidans, and Streptomyces xanthophaeus, and relevant data have been reported.
Cyclo-(Pro-Gly) (CAS# 19179-12-5, molecular formula C₇H₁₀N₂O₂, molecular weight 154.17) is an alkaloid isolated from green algae Ulva prolifera. It possesses antialgal, anti-amnestic, and neuroprotection activities. The compound is a product of both the mevalonate pathway and the MEP pathway of isoprenoid precursor biosynthesis. It is widely used in biochemical experiments and drug synthesis research. No clinical trials or regulatory approvals have been identified. Storage: powder at -20°C for 3 years or 4°C for 2 years. |
| Molecular Formula |
C7H10N2O2
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|---|---|
| Molecular Weight |
154.1665
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| Exact Mass |
154.074
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| CAS # |
19179-12-5
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| PubChem CID |
193540
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| Appearance |
White to off-white solid
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
447.9±34.0 °C at 760 mmHg
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| Flash Point |
224.7±25.7 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.569
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| LogP |
-2.74
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
11
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| Complexity |
215
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C1C2([H])C([H])([H])C([H])([H])C([H])([H])N2C(C([H])([H])N1[H])=O
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| InChi Key |
OWOHLURDBZHNGG-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H10N2O2/c10-6-4-8-7(11)5-2-1-3-9(5)6/h5H,1-4H2,(H,8,11)
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| Chemical Name |
2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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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 | 6.4863 mL | 32.4317 mL | 64.8635 mL | |
| 5 mM | 1.2973 mL | 6.4863 mL | 12.9727 mL | |
| 10 mM | 0.6486 mL | 3.2432 mL | 6.4863 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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