Cyclo(Pro-Gly)

CAS# 19179-12-5

Cyclo(Pro-Gly)

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Chemical structure

Cyclo(Pro-Gly)

3D structure

Chemical Properties of Cyclo(Pro-Gly)

Cas No. 19179-12-5 SDF Download SDF
PubChem ID 193540 Appearance Powder
Formula C7H10N2O2 M.Wt 154.17
Type of Compound Miscellaneous Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
SMILES C1CC2C(=O)NCC(=O)N2C1
Standard InChIKey OWOHLURDBZHNGG-UHFFFAOYSA-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)
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(Pro-Gly)

The Penicillium oxalicum

Biological Activity of Cyclo(Pro-Gly)

DescriptionCyclo(Pro-Gly) is an active metabolite of piracetam-N-phenylacetyl-L-prolylglycine (GWS-111), it shows a greater resistance to an enzymatic effect than natural neuropeptides. Cyclo-(Gly-Pro) shows cytotoxicity at the concentration of 10 umol/L, it inhibits the growth of Bacillus subtilis with the minimal inhibitory concentration (MIC) value of 0.8, 0.8 g/L.
TargetsAntifection
In vitro

The Endophytic Fungus Strain FTJZZJ09 Isolated from the Bulbs of Fritillaria thunbergii and Its Antibacterial Metabolites[Reference: WebLink]

Microbiology China,2010, 37(10):1475-80.


METHODS AND RESULTS:
In the present study, an endophytic fungus isolate FTJZZJ09, which isolated from the fresh bulbs of Fritillaria thunbergii Miq., was identified as Penicillium chrysogenum based on its morphological characters and internal transcribed spacer (ITS) sequence. After being cultured in the modified CzapeK-DoX medium (3 g/L maltose, 3 g/L peptone A, 0.1 g/L K2HPO4, 0.05 g/L KCl, 0.3 g/L NaNO3, 0.05 g/L MgSO4·7H2O, 0.001 g/L FeSO4·7H2O, pH 6.5), it can secrete antibacterial metabolites under the condition of 28°C in a rotary shaker at 160 r/min for 7 days. Three antibacterial compounds were isolated from the ethyl acetate extract of the fermentation broth by silica gel, they were elucidated as Cyclo(Pro-Gly) , cyclo (Pro-Val) and 2-acetyl-4 (3H) quinazolinone.
CONCLUSIONS:
All the three compounds could inhibit the growth of Bacillus subtilis with the minimal inhibitory concentration (MIC) value of 0.8, 0.8, and 0.4 g/L respectively, while they showed no apparent effects against the growth of Gram-negative bacteria.

The antitumor active component from marine derived actinomycete S1001[Reference: WebLink]

Chinese Journal of Antibiotics, 2006, 31(1):36-38,62.


METHODS AND RESULTS:
To explore the antitumor active component in fermentation of a marine derived actinomycete S1001,8 compounds were isolated and purified by using solvent extraction,silica gel column and preparative HPLC.The separation procedure was traced by a bioassay using tsFT210 cell lines.By means of physico-chemical properties and spectral analyses,the structures of compounds were determined as: 4′,5,7-trihydroxyisoflavone(),4-(2,4-dihydroxybenzamido) benzoic acid (2),cyclo-(Gly-Ala)(3),Cyclo(Pro-Gly) (4),(cyclo)-(Leu-Tyr)(5),cyclo-(Val-Leu)(6),cyclo-(Val-Ile)(7),cyclo-(Phe-Gly)(8),respectively.
CONCLUSIONS:
The antitumor activities of these compounds were assayed by the SRB method against K562 cell line.Compounds 4, 5 and 7 showed cytotoxicity at the concentration of 10 μmol/L.

Protocol of Cyclo(Pro-Gly)

Structure Identification
Journal of Mass Spectrometry Volume 33, Issue 1, pages 25–34, January 1998

Energetics of the cyclo(Pro–Gly) cation fragmentation: a mass spectrometric study and theoretical calculations[Reference: WebLink]


METHODS AND RESULTS:
The energetics of HNCO elimination from the Cyclo(Pro-Gly) radical cation was studied by electron ionization tandem mass spectrometry, photoionization mass spectrometry and RRKM/QET modeling. The heat of formation and vibrational frequencies of the reactant were calculated by density functional theory (DFT). Homodesmotic reactions involving Cyclo(Pro-Gly) were used to derive its heat of formation at 0 K as -72.0±3.0 kcal mol-1 (1 kcal=4.184 kJ). Vibrational frequencies were calculated at the B3LYP/6–31G(d) level. The critical energy for HNCO loss was determined from the experiment, by modeling, to be 1.2±0.1 eV. The heat of formation of the Cyclo(Pro-Gly) radical cation and of the product ion C6H9NO+• at 0 K were determined to be 130.9±3.0 and ⩽182.8±5.0 kcal mol-1, respectively.
CONCLUSIONS:
The salient features of the potential energy profile along the reaction coordinate were probed by DFT calculations.

Cyclo(Pro-Gly) Dilution Calculator

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Preparing Stock Solutions of Cyclo(Pro-Gly)

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.4863 mL 32.4317 mL 64.8635 mL 129.7269 mL 162.1587 mL
5 mM 1.2973 mL 6.4863 mL 12.9727 mL 25.9454 mL 32.4317 mL
10 mM 0.6486 mL 3.2432 mL 6.4863 mL 12.9727 mL 16.2159 mL
50 mM 0.1297 mL 0.6486 mL 1.2973 mL 2.5945 mL 3.2432 mL
100 mM 0.0649 mL 0.3243 mL 0.6486 mL 1.2973 mL 1.6216 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(Pro-Gly)

Streptomyces nigra sp. nov. Is a Novel Actinobacterium Isolated From Mangrove Soil and Exerts a Potent Antitumor Activity in Vitro.[Pubmed:30072967]

Front Microbiol. 2018 Jul 18;9:1587.

A new bacterial strain, designated 452(T), was isolated from the rhizosphere soil of the mangrove Avicennia marina in China. As determined, its cell wall peptidoglycan contained LL-diaminopimelic acid; MK-9(H8) and MK-9(H6) were the major isoprenoid quinones; and iso-C16:0 (31.3%), anteiso-C15:0 (16.9%), and iso-C15:0 (12.5%) were the major cellular fatty acids (>10.0%). Phylogenetic analysis based on the 16S rRNA gene sequence revealed that strain 452(T) formed a distinct lineage in the clade of the genus Streptomyces, and was closely related to S. coerulescens DSM 40146(T) (99.6% sequence identity), S. bellus DSM 40185(T) (99.5%), and S. coeruleorubidus DSM 41172(T) (99.3%). The DNA-DNA relatedness between strain 452(T) and these type strains ranged between 29.3 and 42.3%. Based on the phenotypic, chemotaxonomic, and phylogenetic features, the strain 452(T) is considered to represent a novel species of the genus Streptomyces, for which the name Streptomyces nigra sp. nov. is proposed. The type strain is 452(T) (=KCTC 39960(T) = MCCC 1K03346(T)). Further, strain 452(T) extracts exhibited a pronounced antitumor activity against human cancer cell lines A549, HCT-116, and HepG2, but not against normal human colon cells CCD-18Co. Active substances in the fermentation broth of strain 452(T) were isolated by bioassay-guided analysis, and then purified using a macroporous resin, silica gel, sephadex LX-20 column, and semi-preparative high-performance liquid chromatography (HPLC). Eight proline-containing diketopiperazines, namely, cyclo(Pro-Ala), Cyclo(Pro-Gly), cyclo(Pro-Phe), cyclo(Pro-Met), cyclo(Pro-Val), cyclo(Pro-Leu), cyclo(Pro-Tyr), and cyclo(L-Leu-trans-4-hydroxy-L-Pro), were identified by electrospray ionization mass spectrometry (MS) and nuclear magnetic resonance (NMR). The compounds displayed different levels of cytotoxicity. The highest cytotoxicity was exhibited by cyclo(Pro-Ala) and cyclo(Pro-Met) against A549 cells, and cyclo(Phe-Pro) and cyclo(Pro-Ala) against HCT-116 cells, with average IC50 values equal to 18.5, 27.3, 32.3, and 47.6 mug/mL, respectively. The diversity of diketopiperazines and other chemicals produced by 452(T) was further investigated using gas chromatography (GC)-MS and liquid chromatography (LC)-MS. The analysis revealed 16 types of metabolites with antitumor activity and 16 other types of diketopiperazines. Hence, extracts of the newly identified strain may be used a starting material for the development of antitumor agents.

Chiral Recognition of Diketopiperazine Cyclo(Pro-Gly) and Propranolol Using (-)-Epigallocatechin-3-O-gallate.[Pubmed:26833443]

Chem Pharm Bull (Tokyo). 2016;64(2):142-9.

In the (1)H-NMR spectrum of a solution containing an equimolecular amount of cyclo(L-Pro-Gly), cyclo(D-Pro-Gly) and (-)-epigallocatechin-3-O-gallate (EGCg) in a D2O, a difference in the chemical shift of (1)H-NMR signal for H7alpha, H7beta,8alpha of the Pro residue was observed. Judging from the crystal structures of the 2 : 2 complexes of EGCg and cyclo(L-Pro-Gly), cyclo(D-Pro-Gly), the difference in the chemical shift resulted mainly from a magnetic anisotropic shielding effect by the ring current from the B ring of EGCg. Therefore, it was considered that chirality of Cyclo(Pro-Gly) was recognized by EGCg in the D2O solution. Furthermore, in the (1)H-NMR spectrum of a solution containing an equimolecular amount of racemic propranolol ((R)- and (S)-propranolols) and EGCg in D2O, the (1)H-NMR signal for H2 of the naphthalene group was observed as two doublets, suggesting that the racemic propranolol formed diastereomers of complexes with EGCg; as a result, chirality of propranolol was recognized by EGCg in the D2O solution.

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