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SML0113

Sigma-Aldrich

Brequinar sodium salt hydrate

≥97% (HPLC)

Sinónimos:

6-Fluoro-2-(2′-fluoro[1,1′-biphenyl]-4-yl)-3-methyl-4-quinolinecarboxylic acid sodium hydrate, Biphenquinate sodium hydrate, DuP 785 hydrate, NSC 368390 hydrate

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About This Item

Fórmula empírica (notación de Hill):
C23H14F2NO2·Na · xH2O
Número de CAS:
96187-53-0
Peso molecular:
397.35 (anhydrous basis)
MDL number:
MFCD21363375
UNSPSC Code:
12352200
PubChem Substance ID:
329825165
NACRES:
NA.77

Quality Level

100

assay

≥97% (HPLC)

form

powder

color

off-white to brown

solubility

DMSO: ≥5 mg/mL

storage temp.

2-8°C

SMILES string

O.[Na+].Cc1c(nc2ccc(F)cc2c1C([O-])=O)-c3ccc(cc3)-c4ccccc4F

InChI

1S/C23H15F2NO2.Na.H2O/c1-13-21(23(27)28)18-12-16(24)10-11-20(18)26-22(13)15-8-6-14(7-9-15)17-4-2-3-5-19(17)25;;/h2-12H,1H3,(H,27,28);;1H2/q;+1;/p-1

InChI key

IZXTTXFXRQGHKO-UHFFFAOYSA-M

Application

Brequinar sodium salt hydrate has been used as a dihydroorotate dehydrogenase (DHODH) inhibitor:
  • in drug response assays
  • to induce depletion of cellular pyrimidine pools
  • in cell proliferation assays

Brequinar sodium salt hydrate may be used in cell signaling studies.

Biochem/physiol Actions

Brequinar exhibits anti-neoplastic activity against refractory solid tumors in human and mouse models. Continuous treatment is required for depletion of pyrimidine pools in the cancer cells and tumor inhibition.
Brequinar inhibits dihydroorotate dehydrogenase (DHODH), the fourth enzyme in the de novo pyrimidine biosynthesis pathway, preventing the synthesis of DNA and RNA. Brequinar has recently been found to have antiviral activity against a broad spectrum of viruses including flaviviruses (dengue virus, West Nile virus, yellow fever virus, and Powassan virus) and also a plus-strand RNA alphavirus (Western equine encephalitis virus) and a negative-strand RNA rhabdovirus (vesicular stomatitis virus).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Identification of new activators of mitochondrial fusion reveals a link between mitochondrial morphology and pyrimidine metabolism
Miret-Casals L, et al.
Cell Chemical Biology, 25(3), 268-278 (2018)
Twana Alkasalias et al.
Cell death discovery, 8(1), 464-464 (2022-11-25)
Highly specific and potent inhibitors of dihydroorotate dehydrogenase (DHODH), an essential enzyme of the de novo pyrimidine ribonucleotide synthesis pathway, are in clinical trials for autoimmune diseases, viral infections and cancer. However, because DHODH inhibitors (DHODHi) are immunosuppressants they may
C L Arteaga et al.
Cancer research, 49(16), 4648-4653 (1989-08-15)
Brequinar sodium is a 4-quinolinecarboxylic acid analogue that inhibits dihydroorotate dehydrogenase and subsequent de novo pyrimidine biosynthesis. It has shown dose-dependent antineoplastic activity against several mouse and human tumor models. This trial evaluated Brequinar given as a single daily i.v.
PTEN regulates glutamine flux to pyrimidine synthesis and sensitivity to dihydroorotate dehydrogenase inhibition
Mathur D, et al.
Cancer Discovery, 7(4), 380-390 (2017)
Christopher F Bennett et al.
Nature chemical biology, 17(6), 703-710 (2021-03-17)
The protein complexes of the mitochondrial electron transport chain exist in isolation and in higher order assemblies termed supercomplexes (SCs) or respirasomes (SC I+III2+IV). The association of complexes I, III and IV into the respirasome is regulated by unknown mechanisms.
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