Cyclo(L-Leu-L-Pro)
(Synonyms: Maculosin 6) 目录号 : GC43342
A diketopiperazine metabolite
Cas No.:2873-36-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Cyclo(L-Leu-L-Pro) is a diketopiperazine metabolite that has been isolated from various bacterial and fungal species including Streptomyces. It is active against twelve strains of vancomycin-resistant enterococci (VRE) with MIC values of 12.5 µg/ml for E. faecalis strains K-99-34, K-00-184, and K-00-221. It also inhibits growth of K562, HL-60, and U937 leukemia cells in a concentration-dependent manner when used at concentrations of 1-500 µg/ml. Cyclo(L-Leu-L-Pro) also has antifouling activity, inhibiting attachment of B. amphitrite larva with an EC50 value of 0.15 mM.
| Cas No. | 2873-36-1 | SDF | |
| 别名 | Maculosin 6 | ||
| Canonical SMILES | O=C([C@H](CC(C)C)N1)N2[C@](CCC2)([H])C1=O | ||
| 分子式 | C11H18N2O2 | 分子量 | 210.3 |
| 溶解度 | Methanol: 50 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.7551 mL | 23.7756 mL | 47.5511 mL |
| 5 mM | 0.951 mL | 4.7551 mL | 9.5102 mL |
| 10 mM | 0.4755 mL | 2.3776 mL | 4.7551 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Cyclo(L-Leucyl-L-Prolyl) from Lactobacillus coryniformis BCH-4 inhibits the proliferation of Aspergillus flavus: an in vitro to in silico approach
Arch Microbiol 2022 Apr 19;204(5):267.PMID:35438350DOI:10.1007/s00203-022-02884-z.
Fungal spoilage led to a considerable economic loss of foodstuff which ultimately affects public health due to mycotoxins production. Moreover, the consumption of commercial antifungal drugs creates side effects and develops antifungal resistance. To overcome these challenges, the current work was aimed to investigate novel antifungal cyclic dipeptide (CDP) from Lactobacillus coryniformis (Loigolactobacillus coryniformis) BCH-4. CDPs have flexible, cyclic, and stable conformation. The proline-based CDPs provide additional structural compatibility and bio-functional values. Keeping in view, high-performance liquid chromatography (HPLC) was performed to explore Cyclo(L-Leu-L-Pro) from L. coryniformis BCH-4. The HPLC detected concentration (135 ± 7.07 mg/mL) exhibited in vitro antifungal activity of 5.66 ± 0.57 mm (inhibitory zone) against Aspergillus flavus. Based on these results, Cyclo(L-Leu-L-Pro) was used as a bioprotectant for selected food samples (grapes, lemon, cashew nuts, and almonds). A significant impact of Cyclo(L-Leu-L-Pro) was observed in contrast with MRS broth (control) and cell-free supernatant. In silico molecular docking analysis of this CDP was carried out against FAD glucose dehydrogenase, dihydrofolate reductase, and urate oxidase of A. flavus as target proteins. Among these proteins, FAD glucose dehydrogenase exerted strong interactions with Cyclo(L-Leu-L-Pro) having S-score of - 8.21. The results evaluated that the detected CDP has strong interactions with selected proteins, causing excellent growth inhibition of A. flavus. Therefore, Cyclo(L-Leu-L-Pro) could be used as a potent bioprotectant against food-borne pathogenic fungi.
Identification of an early stage biofilm inhibitor from Veillonella tobetsuensis
Anaerobe 2018 Aug;52:86-91.PMID:29908228DOI:10.1016/j.anaerobe.2018.06.005.
Oral biofilm, the cause of dental caries and periodontal diseases, consists of multiple bacterial species. Streptococcus spp. and Veillonella spp. have been reported as to be initial and early colonizers of oral biofilms. Our previous studies showed that Veillonella tobetsuensis may play an important role on the development of S. gordonii biofilms without coaggregation involving extracellular biomolecules. In this study, the effect of a cyclic dipeptide autoinducer from culture supernatants from V. tobetsuensis at late-exponential growth phase on S. gordonii biofilm was examined. The cyclic dipeptide, identified as Cyclo (-L-Leu-L-Pro) by gas chromatography/mass spectrometry, inhibited the development of S. gordonii biofilm. Furthermore, Cyclo (-L-Leu-L-Pro) appeared not to cause bactericidal effects on planktonic cells of S. gordonii. This is the first report that oral Veillonella produces Cyclo (-L-Leu-L-Pro) in their culture supernatants. Moreover, the results of this study suggest that Cyclo (-L-Leu-L-Pro) may have an application to inhibit early stage development of oral biofilms.
Structural Identification, Synthesis and Biological Activity of Two Volatile Cyclic Dipeptides in a Terrestrial Vertebrate
Sci Rep 2020 Mar 9;10(1):4303.PMID:32152427DOI:10.1038/s41598-020-61312-8.
Single substances within complex vertebrate chemical signals could be physiologically or behaviourally active. However, the vast diversity in chemical structure, physical properties and molecular size of semiochemicals makes identifying pheromonally active compounds no easy task. Here, we identified two volatile cyclic dipeptides, Cyclo(L-Leu-L-Pro) and cyclo(L-Pro-L-Pro), from the complex mixture of a chemical signal in terrestrial vertebrates (lizard genus Sceloporus), synthesised one of them and investigated their biological activity in male intra-specific communication. In a series of behavioural trials, lizards performed more chemosensory behaviour (tongue flicks, lip smacks and substrate lickings) when presented with the synthesised cyclo(L-Pro-L-Pro) chemical blend, compared to the controls, the Cyclo(L-Leu-L-Pro) blend, or a combined blend with both cyclic dipeptides. The results suggest a potential semiochemical role of cyclo(L-Pro-L-Pro) and a modulating effect of Cyclo(L-Leu-L-Pro) that may depend on the relative concentration of both compounds in the chemical signal. In addition, our results stress how minor compounds in complex mixtures can produce a meaningful behavioural response, how small differences in structural design are crucial for biological activity, and highlight the need for more studies to determine the complete functional landscape of biologically relevant compounds.
Mycotoxins from Fusarium proliferatum: new inhibitors of papain-like cysteine proteases
Braz J Microbiol 2020 Sep;51(3):1169-1175.PMID:32189177DOI:10.1007/s42770-020-00256-7.
Papain-like cysteine proteases (PLCPs) in plants are essential to prevent phytopathogen invasion. In order to search for cysteine protease inhibitors and to investigate compounds that could be associated to pineapple Fusarium disease, a chemistry investigation was performed on Fusarium proliferatum isolated from Ananas comosus (pineapple) and cultivated in Czapek medium. From F. proliferatum extracts, nine secondary metabolites were isolated and characterized by nuclear magnetic resonance spectroscopy and mass spectrometry experiments: beauvericin (1), fusaric acid (2), N-ethyl-3-phenylacetamide (3), N-acetyltryptamine (4), cyclo(L-Val-L-Pro) cyclodipeptide (5), Cyclo(L-Leu-L-Pro) cyclodipeptide (6), Cyclo(L-Leu-L-Pro) diketopiperazine (7), 2,4-dihydroxypyrimidine (8), and 1H-indole-3-carbaldehyde (9). Compounds 1, 3, and 6 showed significant inhibition of papain, with IC50 values of 25.3 ± 1.9, 39.4 ± 2.5, and 7.4 ± 0.5 μM, respectively. Compound 1 also showed significant inhibition against human cathepsins V and B with IC50 of 46.0 ± 3.0 and 6.8 ± 0.7 μM, respectively. The inhibition of papain by mycotoxins (fusaric acid and beauvericin) may indicate a mechanism of Fusarium in the roles of infection process.
Antioxidant constituents in distillation residue of Awamori spirits
J Agric Food Chem 2007 Jan 10;55(1):75-9.PMID:17199316DOI:10.1021/jf062029d.
Constituents in a distillation residue of Awamori (millet spirits) and their antioxidant activity are investigated in this study. The supernatant of the distillation residue obtained by centrifugation was partitioned with n-hexane, chloroform, ethyl acetate, and n-butanol against water to afford the corresponding solubles. Among them, n-hexane and chloroform solubles showed higher antioxidant potency than l-ascorbic acid by the bleomycin-Fe method. In chloroform solubles, seven cyclic dipeptides were identified along with ethyl 2-pyrrolidione-5-carboxylate, tyrosol, and ethyl p-hydoroxyphenyllactate. Antioxidant activity of ethyl p-hydoroxyphenyllactate was 4.2 times that of l-ascorbic acid, whereas cyclic dipeptides showed activity 0.89-1.29 times as strong as that of l-ascorbic acid. On the other hand, scavenging effect of cyclic dipeptides against O(2)(-.) and OH(.) by using electron spin resonance was also investigated. In the results, cyclo(l-Ile-l-Pro) showed significantly strong inhibitory effect against OH(.) (95.4% at 2.5 x 10-3 M) and cyclo(l-Phe-l-Pro), cyclo(l-Pro-l-Val), and Cyclo(L-Leu-L-Pro) inhibited OH(.) 64.9, 54.1, and 51.0%, respectively, whereas alpha-tocopherol showed 37.7% inhibition, though only a few cyclic dipeptides weakly inhibited O(2)(-.).