| Identification | Back Directory | [Name]
N-(dibenzo[b,d]furan-3-yl)-5-nitrofuran-2-carboxamide | [CAS]
329198-87-0 | [Synonyms]
C-178
N-(3-Dibenzofuranyl)-5-nitro-2-furancarboxamide
2-Furancarboxamide, N-3-dibenzofuranyl-5-nitro-
N-(dibenzo[b,d]furan-3-yl)-5-nitrofuran-2-carboxamide | [Molecular Formula]
C17H10N2O5 | [MOL File]
329198-87-0.mol | [Molecular Weight]
322.27 |
| Chemical Properties | Back Directory | [Melting point ]
>225°C (dec.) | [Boiling point ]
448.3±35.0 °C(Predicted) | [density ]
1.506±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Soluble in DMSO (up to 25 mg/ml) | [form ]
solid | [pka]
11.35±0.43(Predicted) | [color ]
Orange | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. |
| Hazard Information | Back Directory | [Description]
C-178 is a covalent inhibitor of stimulator of interferon genes (STING). It binds to Cys91 on STING to block its palmitoylation and prevents recruitment and phosphorylation of TBK1 in HEK293T cells. C-178 (0.01-1.25 μM) selectively reduces STING-, but not RIG-I- or TBK1-, mediated IFN-β reporter activity in HEK293 cells. It also prevents increases in Ifnb1 expression in bone marrow-derived macrophages (BMDMs) induced by cyclic di-GMP , double-stranded DNA, and LPS when used at a concentration of 0.5 μM. | [Uses]
N-?(3-?Dibenzofuranyl)-?5-?nitro-2-?furancarboxamide is synthesized from Dibenzo[b,d]furan-3-amine (D418205), which is a building block used as a reactant in the preparation of dibenzofuryl(phosphonomethyl)alanines as endothelin converting enzyme inhibitors. | [in vitro]
C-178 targets the poorly characterized N-terminal portion of mmSTING that includes the transmembrane domains. Moreover, C-178 interferes with this process by inhibiting the palmitoylation of STING. C-178 does not appreciably affect STING responses in human cells.C-178 (0-1 μM; 1 hour) alone does not appreciably affect the gene expression profile of BMDMs. In addition, it inhibits the CMA-induced phosphorylation of TBK1.C-178 (1 μM; 1 hour) decreases cdG, dsDNA, CMA and LPS-induced Ifnb1 expression in mouse bone marrow-derived macrophages.C-178 (1 μM; 0.5-4 hours) inhibits the CMA-induced p-TBK1 and sting protein expression as a time-dependent manner in mouse embryonic fibroblasts. | [References]
1) Haag?et al.?(2018),?Targeting STING with covalent small-molecule inhibitors; Nature?559?269 |
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BOC Sciences
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DC Chemicals
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