N3633
β-Naphthoflavone
≥98%
Synonym(s):
beta-Naphthoflavone, 5,6-Benzoflavone, BNF
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About This Item
Empirical Formula (Hill Notation):
C19H12O2
CAS Number:
Molecular Weight:
272.30
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
227-958-4
Beilstein/REAXYS Number:
18991
MDL number:
Assay:
≥98%
InChI key
OUGIDAPQYNCXRA-UHFFFAOYSA-N
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
SMILES string
O=C1C=C(Oc2ccc3ccccc3c12)c4ccccc4
assay
≥98%
color
off-white to yellow
Quality Level
Gene Information
rat ... Gabra2(29706)
storage temp.
2-8°C
Related Categories
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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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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)
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)
Fabienne Fontao et al.
Toxicological sciences : an official journal of the Society of Toxicology, 160(2), 230-243 (2017-10-04)
We have previously shown that cytochrome P450 1A1 (CYP1A1) was highly induced for a long period of time in a patient who had been poisoned by 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD), a compound known to activate the aryl hydrocarbon receptor (AhR). During that period
Werner Borken et al.
Scientific reports, 6, 39072-39072 (2016-12-16)
Biological N2 fixation (BNF) in the rhizosphere of Podocarpaceae is currently attributed to unspecific diazotrophs with negligible impact on N acquisition. Here, we report specific and high associative BNF in dead cells of root nodules of Lepidothamnus fonkii distributed in
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)
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