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Cyclo(Gly-L-Pro)

CAS# 3705-27-9

Cyclo(Gly-L-Pro)

Catalog No. BCN4059----Order now to get a substantial discount!

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Chemical structure

Cyclo(Gly-L-Pro)

3D structure

Chemical Properties of Cyclo(Gly-L-Pro)

Cas No. 3705-27-9 SDF Download SDF
PubChem ID 126154 Appearance Powder
Formula C7H10N2O2 M.Wt 154.2
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (8aS)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
SMILES C1CC2C(=O)NCC(=O)N2C1
Standard InChIKey OWOHLURDBZHNGG-YFKPBYRVSA-N
Standard InChI InChI=1S/C7H10N2O2/c10-6-4-8-7(11)5-2-1-3-9(5)6/h5H,1-4H2,(H,8,11)/t5-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Cyclo(Gly-L-Pro)

The roots of Panax notoginseng (Burk.)F.H.Chen

Biological Activity of Cyclo(Gly-L-Pro)

DescriptionCyclo(Gly-(L)-Pro) shows immunostimulatory properties. Cyclo(Gly-l-Pro) exhibits potent inhibition of TNF-α release with the IC50 values of 4.5 ug/mL, respectively, it also exhibits significant diminution of IL-1β and IL-6 mRNA-expression levels and NO production.
TargetsIFN-γ | IL Receptor | TNF-α | NO
In vitro

Induction of immune-related gene expression in Ctenopharyngodon idella kidney cells by secondary metabolites from immunostimulatory Alcaligenes faecalis FY-3.[Pubmed: 22606987 ]

Scand J Immunol. 2012 Aug;76(2):131-40.

This study was undertaken to isolate active secondary metabolites from immunostimulatory Alcaligenes faecalis FY-3 and evaluate their activities using grass carp Ctenopharyngodon idella kidney (CIK) cells.
METHODS AND RESULTS:
By applying chromatography techniques and successive recrystallization, three purified metabolites were obtained and identified by spectral data (mass spectrometry and nuclear magnetic resonance) as: (1) phenylacetic acid, (2) p-hydroxyphenylacetylamide and (3) Cyclo(Gly-L-Pro). CIK cells were stimulated by different concentrations (1, 10 and 100 μg/ml) of the isolated compounds, and expression of MyD88, IL-1β, TNF-α, type I-IFN and IL-8 genes at different time points (2, 8 and 24 h) post-stimulation was quantified by real-time PCR. The known immunostimulatory agent lipopolysaccharide (LPS) was used as a positive control. To analyse whether these compounds are toxic to the cells, the methyl tetrazolium assay was employed to measure changes in cell viability. The obtained results revealed that transcribing level of MyD88, an important adaptor molecule in toll-like receptor signalling pathway, was augmented remarkably by all the three isolated compounds and LPS as early as 2-h exposure. These compounds also induced gene expression of cytokines such as IL-1β, TNF-α and type I-IFN. Under the experimental conditions, none of the test compounds is toxic to the CIK cells.
CONCLUSIONS:
These findings demonstrate that the immunostimulatory properties of the three metabolites [phenylacetic acid, p-hydroxyphenylacetylamide and Cyclo(Gly-L-Pro) ] from A. faecalis FY-3 in CIK cells and highlight the potential of using these metabolites as immunostimulants in fish aquaculture.

Attenuation of TNF-α secretion by L-proline-based cyclic dipeptides produced by culture broth of Pseudomonas aeruginosa.[Pubmed: 26546220 ]

Bioorg Med Chem Lett. 2015 Dec 15;25(24):5756-61.


METHODS AND RESULTS:
To identify small molecule inhibitors of TNF-α, bioassay- and LC-MS-guided chemical investigation on EtOAc extract of Pseudomonas aeruginosa ABS-36 culture broth (EEPA) was performed, which yielded four proline-based cyclic dipeptides, Cyclo(Gly-L-Pro) (1), cyclo(l-Pro-l-Phe) (2), cyclo(trans-4-hydroxy-l-Pro-l-Phe) (3) and cyclo(trans-4-hydroxy-l-Pro-l-Leu) (4). Compounds 1 and 3 exhibited potent inhibition of TNF-α release with IC50 values of 4.5 and 14.2μg/mL, respectively, while EEPA showed IC50 of 38.8μg/mL under lipopolysaccharide treated RAW 264.7 cell ELISA assay. Also, marked attenuation of mRNA-expression of TNF-α was shown by all compounds. In vivo testing in rats of EEPA and chemically synthesized 4 validated significant TNF-α reduction with 51% (500mg/kg) and 79% (50mg/kg), respectively. In addition, all compounds exhibited significant diminution of IL-1β and IL-6 mRNA-expression levels and NO production.
CONCLUSIONS:
All samples displayed only weak toxicity to lipopolysaccharide-induced RAW 264.7 cells.

Cyclo(Gly-L-Pro) Dilution Calculator

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Preparing Stock Solutions of Cyclo(Gly-L-Pro)

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.4851 mL 32.4254 mL 64.8508 mL 129.7017 mL 162.1271 mL
5 mM 1.297 mL 6.4851 mL 12.9702 mL 25.9403 mL 32.4254 mL
10 mM 0.6485 mL 3.2425 mL 6.4851 mL 12.9702 mL 16.2127 mL
50 mM 0.1297 mL 0.6485 mL 1.297 mL 2.594 mL 3.2425 mL
100 mM 0.0649 mL 0.3243 mL 0.6485 mL 1.297 mL 1.6213 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Cyclo(Gly-L-Pro)

Induction of immune-related gene expression in Ctenopharyngodon idella kidney cells by secondary metabolites from immunostimulatory Alcaligenes faecalis FY-3.[Pubmed:22606987]

Scand J Immunol. 2012 Aug;76(2):131-40.

This study was undertaken to isolate active secondary metabolites from immunostimulatory Alcaligenes faecalis FY-3 and evaluate their activities using grass carp Ctenopharyngodon idella kidney (CIK) cells. By applying chromatography techniques and successive recrystallization, three purified metabolites were obtained and identified by spectral data (mass spectrometry and nuclear magnetic resonance) as: (1) phenylacetic acid, (2) p-hydroxyphenylacetylamide and (3) cyclo-(Gly-(L)-Pro). CIK cells were stimulated by different concentrations (1, 10 and 100 mug/ml) of the isolated compounds, and expression of MyD88, IL-1beta, TNF-alpha, type I-IFN and IL-8 genes at different time points (2, 8 and 24 h) post-stimulation was quantified by real-time PCR. The known immunostimulatory agent lipopolysaccharide (LPS) was used as a positive control. To analyse whether these compounds are toxic to the cells, the methyl tetrazolium assay was employed to measure changes in cell viability. The obtained results revealed that transcribing level of MyD88, an important adaptor molecule in toll-like receptor signalling pathway, was augmented remarkably by all the three isolated compounds and LPS as early as 2-h exposure. These compounds also induced gene expression of cytokines such as IL-1beta, TNF-alpha and type I-IFN. Under the experimental conditions, none of the test compounds is toxic to the CIK cells. These findings demonstrate that the immunostimulatory properties of the three metabolites [phenylacetic acid, p-hydroxyphenylacetylamide and cyclo-(Gly-(L)-Pro)] from A. faecalis FY-3 in CIK cells and highlight the potential of using these metabolites as immunostimulants in fish aquaculture.

Attenuation of TNF-alpha secretion by L-proline-based cyclic dipeptides produced by culture broth of Pseudomonas aeruginosa.[Pubmed:26546220]

Bioorg Med Chem Lett. 2015 Dec 15;25(24):5756-61.

To identify small molecule inhibitors of TNF-alpha, bioassay- and LC-MS-guided chemical investigation on EtOAc extract of Pseudomonas aeruginosa ABS-36 culture broth (EEPA) was performed, which yielded four proline-based cyclic dipeptides, Cyclo(Gly-L-Pro) (1), cyclo(l-Pro-l-Phe) (2), cyclo(trans-4-hydroxy-l-Pro-l-Phe) (3) and cyclo(trans-4-hydroxy-l-Pro-l-Leu) (4). Compounds 1 and 3 exhibited potent inhibition of TNF-alpha release with IC50 values of 4.5 and 14.2mug/mL, respectively, while EEPA showed IC50 of 38.8mug/mL under lipopolysaccharide treated RAW 264.7 cell ELISA assay. Also, marked attenuation of mRNA-expression of TNF-alpha was shown by all compounds. In vivo testing in rats of EEPA and chemically synthesized 4 validated significant TNF-alpha reduction with 51% (500mg/kg) and 79% (50mg/kg), respectively. In addition, all compounds exhibited significant diminution of IL-1beta and IL-6 mRNA-expression levels and NO production. All samples displayed only weak toxicity to lipopolysaccharide-induced RAW 264.7 cells.

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