Cyclo(Phe-Pro)CAS# 14705-60-3 |
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| Cas No. | 14705-60-3 | SDF | Download SDF |
| PubChem ID | 99895 | Appearance | Powder |
| Formula | C14H16N2O2 | M.Wt | 244.29 |
| Type of Compound | Miscellaneous | Storage | Desiccate at -20°C |
| Solubility | DMSO : 125 mg/mL (511.69 mM; Need ultrasonic) | ||
| Chemical Name | 3-benzyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione | ||
| SMILES | C1CC2C(=O)NC(C(=O)N2C1)CC3=CC=CC=C3 | ||
| Standard InChIKey | QZBUWPVZSXDWSB-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C14H16N2O2/c17-13-12-7-4-8-16(12)14(18)11(15-13)9-10-5-2-1-3-6-10/h1-3,5-6,11-12H,4,7-9H2,(H,15,17) | ||
| 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. |
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| 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. |
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| 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. | ||
| Description | Cyclo(Phe-Pro) inhibition of cholera toxin and toxin-coregulated pilus production correlated with reduced transcription of the virulence regulator tcpPH and was alleviated by overexpression of tcpPH.Cyclo(Phe-Pro) has been shown to inhibit cancer cell growth and induce apoptosis in HT-29 colon cancer cells. |
| Targets | PARP | Caspase | NF-kB | IkB | IKK |
| In vitro | Caspase-3 activation and induction of PARP cleavage by cyclic dipeptide cyclo(Phe-Pro) in HT-29 cells.[Pubmed: 16309216]Anticancer Res. 2005 Nov-Dec;25(6B):4197-202.Cyclo(Phe-Pro) has been shown to inhibit cancer cell growth and induce apoptosis in HT-29 colon cancer cells. |
| In vivo | Cyclo(Phe-Pro) produced by the human pathogen Vibrio vulnificus inhibits host innate immune responses through the NF-κB pathway.[Pubmed: 25561711]Infect Immun. 2015 Mar;83(3):1150-61.Cyclo(Phe-Pro) (cFP) is a secondary metabolite produced by certain bacteria and fungi. Although recent studies highlight the role of Cyclo(Phe-Pro) in cell-to-cell communication by bacteria, its role in the context of the host immune response is poorly understood. In this study, we investigated the role of Cyclo(Phe-Pro) produced by the human pathogen Vibrio vulnificus in the modulation of innate immune responses toward the pathogen. |
| Kinase Assay | The cyclic dipeptide cyclo(Phe-Pro) inhibits cholera toxin and toxin-coregulated pilus production in O1 El Tor Vibrio cholerae.[Pubmed: 20453095]Vibrio cholerae ToxR downregulates virulence factor production in response to cyclo(Phe-Pro).[Pubmed: 23982069]MBio. 2013 Aug 27;4(5):e00366-13.Vibrio cholerae is an aquatic organism that causes the severe acute diarrheal disease cholera. The ability of V. cholerae to cause disease is dependent upon the production of two critical virulence determinants, cholera toxin (CT) and the toxin-coregulated pilus (TCP). The expression of the genes that encode for CT and TCP production is under the control of a hierarchical regulatory system called the ToxR regulon, which functions to activate virulence gene expression in response to in vivo stimuli. Cyclic dipeptides have been found to be produced by numerous bacteria, yet their biological function remains unknown. V. cholerae has been shown to produce Cyclo(Phe-Pro). Previous studies in our laboratory demonstrated that Cyclo(Phe-Pro) inhibited V. cholerae virulence factor production. J Bacteriol. 2010 Jul;192(14):3829-32.Cyclo(Phe-Pro) is a cyclic dipeptide produced by multiple Vibrio species.
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Cyclo(Phe-Pro) Dilution Calculator
Cyclo(Phe-Pro) Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 4.0935 mL | 20.4675 mL | 40.935 mL | 81.8699 mL | 102.3374 mL |
| 5 mM | 0.8187 mL | 4.0935 mL | 8.187 mL | 16.374 mL | 20.4675 mL |
| 10 mM | 0.4093 mL | 2.0467 mL | 4.0935 mL | 8.187 mL | 10.2337 mL |
| 50 mM | 0.0819 mL | 0.4093 mL | 0.8187 mL | 1.6374 mL | 2.0467 mL |
| 100 mM | 0.0409 mL | 0.2047 mL | 0.4093 mL | 0.8187 mL | 1.0234 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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Caspase-3 activation and induction of PARP cleavage by cyclic dipeptide cyclo(Phe-Pro) in HT-29 cells.[Pubmed:16309216]
Anticancer Res. 2005 Nov-Dec;25(6B):4197-202.
BACKGROUND: Cyclo(Phe-Pro) has been shown to inhibit cancer cell growth and induce apoptosis in HT-29 colon cancer cells. MATERIALS AND METHODS: The molecular mechanisms mediating Cyclo(Phe-Pro)-induced apoptosis in HT-29 cells were investigated. Cells were treated with 5 mM or 10 mM Cyclo(Phe-Pro) for varying times. Immunoblot analysis was used to detect poly(ADP-ribose)polymerase (PARP) cleavage. A fluorescence-based enzymatic assay was used to measure caspase-3 activity. RESULTS: Cyclo(Phe-Pro) (10 mM) induced time-dependent cleavage of PARP, detected as early as 8 hours post treatment. PARP cleavage was blocked by co-administration with the broad-range caspase inhibitor Z-VAD-FMK Cyclo(Phe-Pro) also induced a time-dependent increase (p < 0.01) in caspase-3 activity. This increase in activity was blocked in the presence of the caspase-3 inhibitor Ac-DEVD-CHO. CONCLUSION: These results provide evidence that Cyclo(Phe-Pro)-induced apoptosis in HT-29 cells is mediated by a caspase cascade. These findings warrant further investigation into the potential antitumour activity of Cyclo(Phe-Pro) and its related cyclic dipeptide derivatives.
The cyclic dipeptide cyclo(Phe-Pro) inhibits cholera toxin and toxin-coregulated pilus production in O1 El Tor Vibrio cholerae.[Pubmed:20453095]
J Bacteriol. 2010 Jul;192(14):3829-32.
Cyclo(Phe-Pro) is a cyclic dipeptide produced by multiple Vibrio species. In this work, we present evidence that Cyclo(Phe-Pro) inhibits the production of the virulence factors cholera toxin (CT) and toxin-coregulated pilus (TCP) in O1 El Tor Vibrio cholerae strain N16961 during growth under virulence gene-inducing conditions. The Cyclo(Phe-Pro) inhibition of CT and TCP production correlated with reduced transcription of the virulence regulator tcpPH and was alleviated by overexpression of tcpPH.
Vibrio cholerae ToxR downregulates virulence factor production in response to cyclo(Phe-Pro).[Pubmed:23982069]
MBio. 2013 Aug 27;4(5):e00366-13.
UNLABELLED: Vibrio cholerae is an aquatic organism that causes the severe acute diarrheal disease cholera. The ability of V. cholerae to cause disease is dependent upon the production of two critical virulence determinants, cholera toxin (CT) and the toxin-coregulated pilus (TCP). The expression of the genes that encode for CT and TCP production is under the control of a hierarchical regulatory system called the ToxR regulon, which functions to activate virulence gene expression in response to in vivo stimuli. Cyclic dipeptides have been found to be produced by numerous bacteria, yet their biological function remains unknown. V. cholerae has been shown to produce Cyclo(Phe-Pro). Previous studies in our laboratory demonstrated that Cyclo(Phe-Pro) inhibited V. cholerae virulence factor production. For this study, we report on the mechanism by which Cyclo(Phe-Pro) inhibited virulence factor production. We have demonstrated that exogenous Cyclo(Phe-Pro) activated the expression of leuO, a LysR-family regulator that had not been previously associated with V. cholerae virulence. Increased leuO expression repressed aphA transcription, which resulted in downregulation of the ToxR regulon and attenuated CT and TCP production. The Cyclo(Phe-Pro)-dependent induction of leuO expression was found to be dependent upon the virulence regulator ToxR. Cyclo(Phe-Pro) did not affect toxR transcription or ToxR protein levels but appeared to enhance the ToxR-dependent transcription of leuO. These results have identified leuO as a new component of the ToxR regulon and demonstrate for the first time that ToxR is capable of downregulating virulence gene expression in response to an environmental cue. IMPORTANCE: The ToxR regulon has been a focus of cholera research for more than three decades. During this time, a model has emerged wherein ToxR functions to activate the expression of Vibrio cholerae virulence factors upon host entry. V. cholerae and other enteric bacteria produce Cyclo(Phe-Pro), a cyclic dipeptide that we identified as an inhibitor of V. cholerae virulence factor production. This finding suggested that Cyclo(Phe-Pro) was a negative effector of virulence factor production and represented a molecule that could potentially be exploited for therapeutic development. In this work, we investigated the mechanism by which Cyclo(Phe-Pro) inhibited virulence factor production. We found that Cyclo(Phe-Pro) signaled through ToxR to activate the expression of leuO, a new virulence regulator that functioned to repress virulence factor production. Our results have identified a new arm of the ToxR regulon and suggest that ToxR may play a broader role in pathogenesis than previously known.
Cyclo(Phe-Pro) produced by the human pathogen Vibrio vulnificus inhibits host innate immune responses through the NF-kappaB pathway.[Pubmed:25561711]
Infect Immun. 2015 Mar;83(3):1150-61.
Cyclo(Phe-Pro) (cFP) is a secondary metabolite produced by certain bacteria and fungi. Although recent studies highlight the role of cFP in cell-to-cell communication by bacteria, its role in the context of the host immune response is poorly understood. In this study, we investigated the role of cFP produced by the human pathogen Vibrio vulnificus in the modulation of innate immune responses toward the pathogen. cFP suppressed the production of proinflammatory cytokines, nitric oxide, and reactive oxygen species in a lipopolysaccharide (LPS)-stimulated monocyte/macrophage cell line and in bone marrow-derived macrophages. Specifically, cFP inhibited inhibitory kappaB (IkappaB) kinase (IKK) phosphorylation, IkappaBalpha degradation, and nuclear factor kappaB (NF-kappaB) translocation to the cell nucleus, indicating that cFP affects the NF-kappaB pathway. We searched for genes that are responsible for cFP production in V. vulnificus and identified VVMO6_03017 as a causative gene. A deletion of VVMO6_03017 diminished cFP production and decreased virulence in subcutaneously inoculated mice. In summary, cFP produced by V. vulnificus actively suppresses the innate immune responses of the host, thereby facilitating its survival and propagation in the host environment.
