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Cyclo(L-Pro-L-Val) Sale

(Synonyms: 环(L-脯-L-缬)二肽) 目录号 : GC45416

Cyclo(L-Pro-L-Val)是一种双酮哌嗪,对金黄色葡萄球菌和枯草芽孢杆菌有抗菌活性,其MIC值分别为16.3μg/ml和18.2μg/ml。

Cyclo(L-Pro-L-Val) Chemical Structure

Cas No.:2854-40-2

规格 价格 库存 购买数量
25mg
¥504.00
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50mg
¥924.00
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100mg
¥1,764.00
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250mg
¥3,878.00
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Sample solution is provided at 25 µL, 10mM.

Description

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.

Cyclo(L-Pro-L-Val)是一种双酮哌嗪,对金黄色葡萄球菌和枯草芽孢杆菌有抗菌活性,其MIC值分别为16.3μg/ml和18.2μg/ml[1,2]。Cyclo(L-Pro-L-Val)具有生物防治细菌的抑制活性,特别是对植物致病性革兰氏阳性菌蓝球菌LMG 3605[3]

Cyclo(L-Pro-L-Val) (0.1 or 1mg/mL; 24h)对大肠杆菌有强烈抑制作用[4]。Cyclo(L-Pro-L-Val) (50 or 100μM; 1h)以浓度依赖性显著抑制RAW 264.7小鼠巨噬细胞中LPS(1μg/mL; 24h)诱导的NO生成[5]

使用Cyclo(L-Pro-L-Val) (200μM; 48 or 72h) 处理斑马鱼异种移植模型,Cyclo(L-Pro-L-Val)显著抑制斑马鱼异种移植模型的肿瘤进程[6]。使用Cyclo(L-Pro-L-Val) (100μM; 24h)处理斑马鱼胚胎,与对照组相比,给予Cyclo(L-Pro-L-Val)的斑马鱼胚胎存活率略有增加[6,7]

实验参考方法

Cell experiment [1]:

Cell lines

A mouse macrophage cell line, RAW 264.7

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.

Reaction Conditions

50 or 100μM; 1h

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]:

Animal models

Male C57BL/6J mice

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.

Dosage form

200μM; 48 or 72h

Applications

Cyclo(L-Pro-L-Val) remarkably inhibited the tumor progression in a zebrafish xenograft model.

References:
[1] 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):
[2] 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.

化学性质

Cas No. 2854-40-2 SDF
别名 环(L-脯-L-缬)二肽
Canonical SMILES O=C([C@H](C(C)C)N1)N2[C@](CCC2)([H])C1=O
分子式 C10H16N2O2 分子量 196.2
溶解度 PBS (pH 7.2): 2mg/mL 储存条件 Store at -20°C
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1 mM 5.0968 mL 25.4842 mL 50.9684 mL
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10 mM 0.5097 mL 2.5484 mL 5.0968 mL
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