Cyclo(L-Pro-L-Val) (Synonyms: Cyclo(L-prolyl-L-valine)) |
Catalog No.GC45416
One-Click Copy Product Info
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Cyclo(L-Pro-L-Val) is a diketopiperazine, and it is active against the bacteria Staphylococcus aureus and Bacillus subtilis, which have MICs values of 16.3μg/ml and 18.2μg/ml respectively.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 2854-40-2
Sample solution is provided at 25 µL, 10mM.
Cyclo(L-Pro-L-Val) is a diketopiperazine, and it is active against the bacteria Staphylococcus aureus and Bacillus subtilis, which have MICs values of 16.3μg/ml and 18.2μg/ml respectively[1, 2]. Cyclo(L-Pro-L-Val) has biocontrol bacterial inhibitory activity, especially against the phytopathogenic Gram-positive bacterium Rhodococcus fascians LMG 3605[3].
Cyclo(L-Pro-L-Val) (0.1 or 1mg/mL; 24h) presented the highest promising ability to inhibit the E. coli[4]. Cyclo(L-Pro-L-Val) (50 or 100μM; 1h) markedly inhibited the NO production in a concentration-dependent manner in LPS-treated (1μg/mL; 24h) RAW 264.7 mouse macrophages cells[5].
Cyclo(L-Pro-L-Val) (200μM; 48 or 72h) remarkably inhibited the tumor progression in a zebrafish xenograft model[6]. Cyclo(L-Pro-L-Val) (100μM; 24h) increase slightly the survival rates of zebrafish embryos in the treatment groups compared to the control[6, 7].
References:
[1] BRACK C, MIKOLASCH A, SCHAUER F. 2,5-Diketopiperazines produced by Bacillus pumilus during bacteriolysis of Arthrobacter citreus [J]. Mar Biotechnol (NY), 2014, 16(4): 385-95.
[2] EL-GENDY BEL D, RATEB M E. Antibacterial activity of diketopiperazines isolated from a marine fungus using t-butoxycarbonyl group as a simple tool for purification [J]. Bioorg Med Chem Lett, 2015, 25(16): 3125-8.
[3] CIMMINO A, BEJARANO A, MASI M, et al. Isolation of 2,5-diketopiperazines from Lysobacter capsici AZ78 with activity against Rhodococcus fascians [J]. Nat Prod Res, 2021, 35(23): 4969-77.
[4] NUMAN M, SHAH M, ASAF S, et al. Bioactive Compounds from Endophytic Bacteria Bacillus subtilis Strain EP1 with Their Antibacterial Activities [J]. Metabolites, 2022, 12(12):
[5] LEE D, LEE S R, KANG K S, et al. Bioactive Phytochemicals from Mulberry: Potential Anti-Inflammatory Effects in Lipopolysaccharide-Stimulated RAW 264.7 Macrophages [J]. Int J Mol Sci, 2021, 22(15):
[6] JINENDIRAN S, TENG W, DAHMS H U, et al. Induction of mitochondria-mediated apoptosis and suppression of tumor growth in zebrafish xenograft model by cyclic dipeptides identified from Exiguobacterium acetylicum [J]. Sci Rep, 2020, 10(1): 13721.
[7] FONTANA C M, VAN DOAN H. Zebrafish xenograft as a tool for the study of colorectal cancer: a review [J]. Cell Death Dis, 2024, 15(1): 23.
| Cell experiment [1]: | |
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Cell lines |
A mouse macrophage cell line, RAW 264.7 |
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Preparation Method |
A mouse macrophage cell line, RAW 264.7, was cultured in DMEM containing 4mM L-glutamine, antibiotics (1% penicillin/streptomycin), and 10% fetal bovine serum in humidified air environment at 37℃ in a 5% CO2. RAW264.7 cells (3×104 cells/well) were exposed to the indicated concentrations of Cyclo(L-Pro-L-Val) for 1h and then incubated for an additional 24h with LPS (1μg/mL). At the end of the incubation, each culture supernatant was blended with the Griess reagent to determine NO production by RAW 264.7 cells. Optical density at 540nm of the mixture was determined using a spectrophotometer microplate. |
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Reaction Conditions |
50 or 100μM; 1h |
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Applications |
Cyclo(L-Pro-L-Val) markedly inhibited the NO production in a concentration-dependent manner in LPS-treated RAW 264.7 mouse macrophages cells. |
| Animal experiment [2]: | |
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Animal models |
Male C57BL/6J mice |
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Preparation Method |
For cell labelling, HT-29 cells were incubated with cell tracker CM-Dil dye at a final volume was 20μL/mL for 25min at 37°C. To remove theunstrained dye, cells were washed twice and re-suspended with 1×PBS, pH 7.4 to a final density of 2.1×106 cells/mL. Prior transplantation, CM-Dil labelled cells were assessed for viability using trypan blue exclusion assay. More than >90% of viable cells were used. For xenotransplantation, 48 hours post-fertilization (hpf) wild-type ABiC embryos were anaesthetized in 0.01% tricaine methanesulfonate solution containing 0.3% phenylthiocarbamide. After anesthetization, CM-Dil labelled HT-29 cells grafted into the yolk sac of each zebrafish embryos by using a microinjector IM-300. After injection, embryos were incubated for 1h at 28°C. For confirmation of the visible cell mass at the injection site, zebrafish were transferred to an incubator and maintained at 37°C. Xenograft model for antitumor assay: Five hundred CM-Dil labelled HT-29 xenograft zebrafish embryos were randomly selected and hosed into 4 replicate wells in 12-well cell culture plates. 200μM of Cyclo(L-Pro-L-Val) were treated with transplanted embryos. Before DKPs treatment, the initial fluorescence intensity of transplanted cancer cells was measured at 0 hour post-injection (hpi). At the end of experiment 24, 48, and 72h, all embryos were selected from each well and were photographed under an inverted fluorescence microscope. |
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Dosage form |
200μM; 48 or 72h |
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Applications |
Cyclo(L-Pro-L-Val) remarkably inhibited the tumor progression in a zebrafish xenograft model. |
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References: |
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| Cas No. | 2854-40-2 | SDF | |
| Synonyms | Cyclo(L-prolyl-L-valine) | ||
| Canonical SMILES | O=C([C@H](C(C)C)N1)N2[C@](CCC2)([H])C1=O | ||
| Formula | C10H16N2O2 | M.Wt | 196.2 |
| Solubility | PBS (pH 7.2): 2mg/mL | Storage | Store at -20°C |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.0968 mL | 25.4842 mL | 50.9684 mL |
| 5 mM | 1.0194 mL | 5.0968 mL | 10.1937 mL |
| 10 mM | 509.7 μL | 2.5484 mL | 5.0968 mL |
Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)
g
μL
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Calculation results:
Working concentration: mg/ml;
Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid 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 master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL saline, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.
Quality Control & SDS
- View current batch:
- Purity: >98.00% Appearance: A solid
- COA (Certificate of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 20 reference(s) in Google Scholar.)