beta-Naphthoflavone
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MedKoo CAT#: 540310

CAS#: 6051-87-2

Description: beta-Naphthoflavone is a AhR agonist and antioxidant. It inhibits cigarette smoked-induced DNA damage and tumor development and induces cell cycle arrest in breast cancer cells.


Price and Availability

Size
Price

1g
USD 175
Size
Price

5g
USD 320
Size
Price

beta-Naphthoflavone, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 540310
Name: beta-Naphthoflavone
CAS#: 6051-87-2
Chemical Formula: C19H12O2
Exact Mass: 272.0837
Molecular Weight: 272.3
Elemental Analysis: C, 83.81; H, 4.44; O, 11.75


Synonym: beta-Naphthoflavone; beta-NF

IUPAC/Chemical Name: 3-phenyl-1H-benzo[f]chromen-1-one

InChi Key: OUGIDAPQYNCXRA-UHFFFAOYSA-N

InChi Code: 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 Code: O=C1C2=C3C=CC=CC3=CC=C2OC(C4=CC=CC=C4)=C1


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Wang C, Xu CX, Bu Y, Bottum KM, Tischkau SA. Beta-naphthoflavone (DB06732) mediates estrogen receptor-positive breast cancer cell cycle arrest through AhR-dependent regulation of PI3K/AKT and MAPK/ERK signaling. Carcinogenesis. 2014 Mar;35(3):703-13. doi: 10.1093/carcin/bgt356. Epub 2013 Oct 26. PubMed PMID: 24163404; PubMed Central PMCID: PMC3941744.

2: Chatuphonprasert W, Sangkawat T, Nemoto N, Jarukamjorn K. Suppression of beta-naphthoflavone induced CYP1A expression and lipid-peroxidation by berberine. Fitoterapia. 2011 Sep;82(6):889-95. doi: 10.1016/j.fitote.2011.05.002. Epub 2011 May 23. PubMed PMID: 21624442.

3: Elsherbiny ME, El-Kadi AO, Brocks DR. The effect of beta-naphthoflavone on the metabolism of amiodarone by hepatic and extra-hepatic microsomes. Toxicol Lett. 2010 Jun 2;195(2-3):147-54. doi: 10.1016/j.toxlet.2010.03.019. Epub 2010 Apr 1. PubMed PMID: 20362646.

4: Udomsuk L, Chatuphonprasert W, Jarukamjorn K, Sithithaworn P. Andrographolide Ameliorates Beta-Naphthoflavone-Induced CYP1A Enzyme Activity and Lipid Peroxidation in Hamsters with Acute Opisthorchiasis. J Med Assoc Thai. 2016 Jan;99 Suppl 1:S22-7. PubMed PMID: 26817235.

5: Ferreira RS, Chivittz CD, Santos GS, Zanette J. Cytochrome P450 1A mRNA in the guppy Phalloceros caudimaculatus and response to beta-naphthoflavone and environmental samples. Aquat Toxicol. 2016 Dec;181:86-93. doi: 10.1016/j.aquatox.2016.10.023. Epub 2016 Oct 25. PubMed PMID: 27821351.

6: Fujita Y, Yonehara M, Tetsuhashi M, Noguchi-Yachide T, Hashimoto Y, Ishikawa M. beta-Naphthoflavone analogs as potent and soluble aryl hydrocarbon receptor agonists: improvement of solubility by disruption of molecular planarity. Bioorg Med Chem. 2010 Feb;18(3):1194-203. doi: 10.1016/j.bmc.2009.12.036. Epub 2009 Dec 21. PubMed PMID: 20060304.

7: Shimada Y, Dewa Y, Ichimura R, Suzuki T, Mizukami S, Hayashi SM, Shibutani M, Mitsumori K. Antioxidant enzymatically modified isoquercitrin suppresses the development of liver preneoplastic lesions in rats induced by beta-naphthoflavone. Toxicology. 2010 Feb 9;268(3):213-8. doi: 10.1016/j.tox.2009.12.019. Epub 2010 Jan 5. PubMed PMID: 20045035.

8: Heinrich P, Diehl U, Förster F, Braunbeck T. Improving the in vitro ethoxyresorufin-O-deethylase (EROD) assay with RTL-W1 by metabolic normalization and use of β-naphthoflavone as the reference substance. Comp Biochem Physiol C Toxicol Pharmacol. 2014 Aug;164:27-34. doi: 10.1016/j.cbpc.2014.04.005. Epub 2014 Apr 22. PubMed PMID: 24768776.

9: Stauber KL, Laskin JD, Yurkow EJ, Thomas PE, Laskin DL, Conney AH. Flow cytometry reveals subpopulations of murine epidermal cells that are refractory to induction of cytochrome P-4501A1 by beta-naphthoflavone. J Pharmacol Exp Ther. 1995 May;273(2):967-76. PubMed PMID: 7752102.

10: Ishida K, Taguchi M, Akao T, Hashimoto Y. Involvement of the CYP1A subfamily in stereoselective metabolism of carvedilol in beta-naphthoflavone-treated Caco-2 cells. Biol Pharm Bull. 2009 Mar;32(3):513-6. PubMed PMID: 19252307.

11: Koleva M, Staneva-Stoytcheva D. Effect of nifedipine on the enzyme-inducing activity of phenobarbital and beta-naphthoflavone. Acta Physiol Pharmacol Bulg. 1991;17(2-3):122-8. PubMed PMID: 1819909.

12: Hayashi H, Taniai E, Morita R, Hayashi M, Nakamura D, Wakita A, Suzuki K, Shibutani M, Mitsumori K. Enhanced liver tumor promotion but not liver initiation activity in rats subjected to combined administration of omeprazole and β-naphthoflavone. J Toxicol Sci. 2012;37(5):969-85. PubMed PMID: 23038005.

13: Degen GH. Inhibition of prostaglandin H synthase-catalyzed cooxidation of diethylstilbestrol by alpha-naphthoflavone and beta-naphthoflavone. J Biochem Toxicol. 1988 Spring;3:1-10. PubMed PMID: 3148723.

14: Sun JQ, Lau PP, Strobel HW. Aging modifies the expression of hepatic microsomal cytochromes P-450 after pretreatment of rats with beta-naphthoflavone or phenobarbital. Exp Gerontol. 1986;21(2):65-73. PubMed PMID: 3758228.

15: Lakshmi VM, Hsu FF, Zenser TV. Identification of new 2-amino-3-methylimidazo[4,5-f]quinoline urinary metabolites from beta-naphthoflavone-treated mice. Drug Metab Dispos. 2009 Aug;37(8):1690-7. doi: 10.1124/dmd.109.027342. Epub 2009 May 18. PubMed PMID: 19451400; PubMed Central PMCID: PMC2712437.

16: Brauze D, Januchowski R, Szyfter K. Differences between rats and mice in induction of 4S beta-naphthoflavone-binding protein expression by treatment with beta-naphthoflavone. J Appl Genet. 2002;43(3):371-6. PubMed PMID: 12177527.

17: Chen EP, Chen L, Ji Y, Tai G, Wen YH, Ellens H. A mechanism-based mathematical model of aryl hydrocarbon receptor-mediated CYP1A induction in rats using beta-naphthoflavone as a tool compound. Drug Metab Dispos. 2010 Dec;38(12):2278-85. doi: 10.1124/dmd.110.034421. Epub 2010 Sep 15. PubMed PMID: 20843940.

18: Riviere JL, Devaux A, Gonin O, Monod G. Effect of beta-naphthoflavone and MCPA on liver and kidney drug-metabolizing enzymes from the carp, Cyprinus carpio. Ecotoxicol Environ Saf. 1990 Jun;19(3):276-84. PubMed PMID: 2364910.

19: Shi LZ, Czuprynski CJ. Beta-naphthoflavone causes an AhR-independent inhibition of invasion and intracellular multiplication of Listeria monocytogenes in murine hepatocytes. Microb Pathog. 2009 Nov;47(5):258-66. doi: 10.1016/j.micpath.2009.08.004. Epub 2009 Aug 26. PubMed PMID: 19715752; PubMed Central PMCID: PMC2767476.

20: Yokota H, Inoue H, Taniyama H, Kobayashi T, Iwano H, Kagawa Y, Okada H, Yuasa A. High induction of phenol UDP-glucuronosyltransferase in the kidney medulla of beta-naphthoflavone-treated rats. Biochim Biophys Acta. 1997 Aug 29;1336(2):165-70. PubMed PMID: 9305786.