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N3633

Sigma-Aldrich

β-Naphthoflavone

≥98%

Sinónimos:

beta-Naphthoflavone, 5,6-Benzoflavone, BNF

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About This Item

Fórmula empírica (notación de Hill):
C19H12O2
Número de CAS:
6051-87-2
Peso molecular:
272.30
Beilstein/REAXYS Number:
18991
EC Number:
227-958-4
MDL number:
MFCD00004986
UNSPSC Code:
12352100
PubChem Substance ID:
57654450
NACRES:
NA.22

assay

≥98%

color

off-white to yellow

mp

164-166 °C (lit.)

storage temp.

2-8°C

SMILES string

O=C1C=C(Oc2ccc3ccccc3c12)c4ccccc4

InChI

1S/C19H12O2/c20-16-12-18(14-7-2-1-3-8-14)21-17-11-10-13-6-4-5-9-15(13)19(16)17/h1-12H

InChI key

OUGIDAPQYNCXRA-UHFFFAOYSA-N

Gene Information

rat ... Gabra2(29706)

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General description

β-Naphthoflavone is a polyaromatic hydrocarbon.

Application

β-Naphthoflavone has been used:
  • as aryl hydrocarbon receptor agonist to elucidate its effect on Cyp1A1 expression in embryos of transgenic cytochrome P450 1A1 (cyp1a) reporter zebrafish
  • as AhR agonists, to treat primary normal human epidermal keratinocytes (NHEKs) to study about aryl hydrocarbon receptor (AhR) activation by western blot analysis
  • to determine its effect on the expression of dystrophin (Dp)71
  • to stimulate the expression of causes recombination (Cre) recombinase and to delete the flanking alleles of locus of crossing (x) over, P1 (loxP) sequences

Biochem/physiol Actions

β-Naphthoflavone (BNF) is an exogenous ligand for aryl hydrocarbon receptor (AhR) in humans. It is an inducer of phase I detoxification enzymes (CYPs) and phase II enzymes (UDP-GTs) and NAD(P)H-dependent quinone oxyreductase-1(NQO1). It also induces cytochrome P450 (Cyp1a). BNF represses the expression of Duchenne muscular dystrophy gene, dystrophin (Dp)71 by altering the binding of the transcription factors.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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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Induction of a chloracne phenotype in an epidermal equivalent model by 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin (TCDD) is dependent on aryl hydrocarbon receptor activation and is not reproduced by aryl hydrocarbon receptor knock down
Forrester AR, et al.
Journal of Dermatological Science, 73(1), 10-22 (2014)
The polyaromatic hydrocarbon beta-naphthoflavone alters binding of YY1, Sp1, and Sp3 transcription factors to the Dp71 promoter in hepatic cells
Becerril-Esquivel C, et al.
Molecular Medicine Reports, 17(4), 6150-6155 (2018)
Improvement in aqueous solubility in small molecule drug discovery programs by disruption of molecular planarity and symmetry.
Minoru Ishikawa et al.
Journal of medicinal chemistry, 54(6), 1539-1554 (2011-02-25)
Wei Zhang et al.
Bioorganic & medicinal chemistry, 17(5), 2077-2090 (2009-02-10)
Functionalized benzylidene-indolin-2-ones are widely associated with antiproliferative activity. The scaffold is not normally associated with chemoprevention in spite of the presence of a nitrogen-linked Michael acceptor moiety that may predispose members to induction of NQO1, a widely used biomarker of
Preethi Korangath et al.
Science advances, 6(13), eaay1601-eaay1601 (2020-04-02)
The factors that influence nanoparticle fate in vivo following systemic delivery remain an area of intense interest. Of particular interest is whether labeling with a cancer-specific antibody ligand ("active targeting") is superior to its unlabeled counterpart ("passive targeting"). Using models
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