| Identification | Back Directory | [Name]
Pyrrolo(2,1-F)pyrazine-1,4-dione, 2,3,6,7,8,8A-hexahydro-3-(phenylmethyl)- | [CAS]
14705-60-3 | [Synonyms]
Cyclo(D-phenylalanyl-L-prolyl)
Hexahydro-3-(phenylmethyl)pyrrolo[1,2-a]pyrazine-1,4-dione
Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(phenylmethyl)-
3-(Phenylmethyl)-2,3,6,7,8,8A-hexahydropyrrolo(2,1-F)pyrazine-1,4-dione
Pyrrolo(2,1-F)pyrazine-1,4-dione, 2,3,6,7,8,8A-hexahydro-3-(phenylmethyl)- | [Molecular Formula]
C14H16N2O2 | [MDL Number]
MFCD00101617 | [MOL File]
14705-60-3.mol | [Molecular Weight]
244.29 |
| Chemical Properties | Back Directory | [Boiling point ]
509.5±39.0 °C(Predicted) | [density ]
1.26±0.1 g/cm3(Predicted) | [solubility ]
DMF: 1 mg/ml; Ethanol: 1 mg/ml | [form ]
A solid | [pka]
13.21±0.40(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Uses]
Cyclo(Phe-Pro) (Cyclo(phenylalanylprolyl)) is a quorum-sensing molecule of Vibrio vulnificus that specifically interacts with RIG-I, inhibiting RIG-I polyubiquitination, suppressing IRF-3 activation, and reducing type I interferon production. Cyclo(Phe-Pro) enhances susceptibility to HCV and influenza virus and also alleviates plant aluminum toxicity stress. The mechanism of Cyclo(Phe-Pro) involves the regulation of host immune signaling pathways, bacterial virulence gene expression, and plant antioxidant systems, making it a promising candidate for research in viral infections, bacterial virulence regulation, and agricultural stress resistance[1][2][3]. | [in vivo]
Cyclo(Phe-Pro) (50 mg/kg, i.v., once daily for 3 days) promoted HCV replication and suppressed poly(I:C)-induced antiviral response in the HCV-infected Huh7 subcutaneous xenograft NOD/SCID mouse model[1]. | Animal Model: | Subcutaneous xenograft model of HCV-infected Huh7 cells in NOD/SCID mice[1] | | Dosage: | 50 mg/kg | | Administration: | Intravenous injection (i.v.), once daily for 3 days | | Result: | Reversed poly(I:C)-induced HCV RNA reduction, restoring serum HCV RNA levels. |
| [References]
[1] Lee W, et al. Vibrio vulnificus quorum-sensing molecule cyclo(Phe-Pro) inhibits RIG-I-mediated antiviral innate immunity. Nat Commun. 2018 Apr 23;9(1):1606. DOI:10.1038/s41467-018-04075-1
[2] Bina XR, et al. The cyclic dipeptide cyclo(Phe-Pro) inhibits cholera toxin and toxin-coregulated pilus production in O1 El Tor Vibrio cholerae. J Bacteriol. 2010 Jul;192(14):3829-32. DOI:10.1128/JB.00191-10
[3] Wang Y, et al. Novel application of cyclo(-Phe-Pro) in mitigating aluminum toxicity through oxidative stress alleviation in wheat roots. Environ Pollut. 2024 Dec 15;363(Pt 2):125241. DOI:10.1016/j.envpol.2024.125241 |
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