N3633
β-Naphthoflavone
≥98%
Synonyme(s) :
beta-Naphthoflavone, 5,6-Benzoflavone, BNF
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A propos de cet article
Formule empirique (notation de Hill) :
C19H12O2
Numéro CAS:
Poids moléculaire :
272.30
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
227-958-4
Beilstein/REAXYS Number:
18991
MDL number:
Assay:
≥98%
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Laissez-nous vous aiderInChI 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
Catégories apparentées
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.
Classe de stockage
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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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)
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)
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
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)
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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