| Identification | Back Directory | [Name]
Ribocil-C | [CAS]
1825355-56-3 | [Synonyms]
Ribocil-C
4(3H)-Pyrimidinone, 2-[(3S)-1-[[1-(2-pyrimidinyl)-1H-imidazol-4-yl]methyl]-3-piperidinyl]-6-(2-thienyl)- | [Molecular Formula]
C21H21N7OS | [MOL File]
1825355-56-3.mol | [Molecular Weight]
419.5 |
| Chemical Properties | Back Directory | [Boiling point ]
672.0±65.0 °C(Predicted) | [density ]
1.47±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMSO : ≥ 24.6 mg/mL (58.64 mM) | [form ]
Solid | [pka]
8.44±0.50(Predicted) | [color ]
White to off-white | [SMILES]
O=C1NC([C@@]2([H])CCCN(CC3=CN(C4=NC=CC=N4)C=N3)C2)=NC(C5=CC=CS5)=C1 |
| Hazard Information | Back Directory | [Uses]
Ribocil-C is a highly selective inhibitor of bacterial riboflavin riboswitches. | [Biological Activity]
Ribocil-C is a potent inhibitor of bacterial riboflavin riboswitches. Riboswitches are cis regulatory elements present in non-coding RNA th at specifically bind to natural ligands to regulate gene expression. Ribocil-C blocks the flavin mononucleotide riboswitch-mediated expression of the ribB genewhich is required for riboflavin biosynthesiswith an IC50 value of 23 nM. Ribocil-C inhibited bacterial cell growth of E. coli MB5746 and bacterial burden in a mouse E. coli septicaemia model of infection. | [in vivo]
Higher dose Ribocil-C treatment groups (60 and 120 mg kg21 ribocil-C) demonstrate a dose-dependent reduction in bacterial burden of 1.87 and 3.29 log10[CFU per g spleen] reduction respectively versus shamtreated mice, without mortality or gross effects of toxicity observed[2]. | [References]
[1] Wang H, et al. Dual-Targeting Small-Molecule Inhibitors of the Staphylococcus aureus FMN Riboswitch DisruptRiboflavin Homeostasis in an Infectious Setting. Cell Chem Biol. 2017 May 18;24(5):576-588. DOI:10.1016/j.chembiol.2017.03.014
[2] Howe JA, et al. Selective small-molecule inhibition of an RNA structural element. Nature. 2015 Oct 29;526(7575):672-7. DOI:10.1038/nature15542 |
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