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N3633

Sigma-Aldrich

β-Naphthoflavone

≥98%

Sinonimo/i:

beta-Naphthoflavone, 5,6-Benzoflavone, BNF

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About This Item

Formula empirica (notazione di Hill):
C19H12O2
Numero CAS:
6051-87-2
Peso molecolare:
272.30
Beilstein:
18991
Numero CE:
227-958-4
Numero MDL:
MFCD00004986
Codice UNSPSC:
12352100
ID PubChem:
57654450
NACRES:
NA.22

Saggio

≥98%

Colore

off-white to yellow

Punto di fusione

164-166 °C (lit.)

Temperatura di conservazione

2-8°C

Stringa SMILE

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
OUGIDAPQYNCXRA-UHFFFAOYSA-N

Informazioni sul gene

rat ... Gabra2(29706)

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Descrizione generale

β-Naphthoflavone is a polyaromatic hydrocarbon.

Applicazioni

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

Azioni biochim/fisiol

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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

Certificati d'analisi (COA)

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Sigma-Aldrich

R3501

Rifampicin

Aroclor 1254 ampule of 50 mg, analytical standard

Supelco

48586

Aroclor 1254

Sulfaphenazole ≥98%

Sigma-Aldrich

S0758

Sulfaphenazole

Transcriptome regulation and chromatin occupancy by E2F3 and MYC in mice
Tang X, et al.
Scientific data, 3(4), 160008-160008 (2016)
Cyp1a reporter zebrafish reveals target tissues for dioxin
Kim KH, et al.
Aquatic Toxicology (Amsterdam, Netherlands), 134, 57-65 (2013)
beta-naphthoflavone interferes with cyp1c1, cox2 and IL-8 gene transcription and leukotriene B4 secretion in Atlantic cod (Gadus morhua) head kidney cells during inflammation
Holen E and Olsvik P
Fish & Shellfish Immunology, 54(1), 128-134 (2016)
Ryeo-Ok Kim et al.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, 157(2), 172-182 (2012-11-28)
CYP1A is involved in the metabolism of diverse chemicals, including polycyclic aromatic hydrocarbons and alkylated-PAHs, as a first line of detoxification mechanism. First, we identified and characterized the CYP1A gene from the marine medaka, Oryzias melastigma. O. melastigma CYP1A (Om-CYP1A)
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)
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