Cat. No.: HY-125833

Alpha-Naphthoflavone

10 Cited Publications

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Based on 10 publication(s) in Google Scholar

Alpha-Naphthoflavone is an orally active flavonoid that is a potent, competitive inhibitor of aromatasearomatase. IC 50 and K I value were 0.5 and 0.2 microns. Alpha-Naphthoflavone can inhibit cell proliferation and induce apoptosis.

For research use only. We do not sell to patients.

Purity: 99.76%
CAS No.: 604-59-1
Formula: C₁₉H₁₂O₂
Molecular Weight:272.30

Storage:

4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Alpha-Naphthoflavone Chemical Structure

CAS No.: 604-59-1

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Fluorescent Dye

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biological Activity
- Description
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Publications (10)
Solvent & Solubility
- In Vitro
Purity & Documentation
References
Help & FAQs
Classifications
Bioz

Biological Activity

Description

IC₅₀ & Target

Aromatase

All Cytochrome P450 Isoforms :

Cellular Effect

Cell Line	Type	Value	Description	References
2008	IC₅₀	11.3 μM Compound: 14	Inhibition of MRP1 (unknown origin) expressed in human 2008 cells assessed as calcein-AM accumulation preincubated for 30 mins before calcein-AM addition measured up to 90 mins by fluorescence assay Inhibition of MRP1 (unknown origin) expressed in human 2008 cells assessed as calcein-AM accumulation preincubated for 30 mins before calcein-AM addition measured up to 90 mins by fluorescence assay	[PMID: 23851114]
A2780 ADR	IC₅₀	24.6 μM Compound: 14	Inhibition of p-glycoprotein (unknown origin) expressed in human A2780Adr cells assessed as calcein-AM accumulation preincubated for 30 mins before calcein-AM addition measured up to 90 mins by fluorescence assay Inhibition of p-glycoprotein (unknown origin) expressed in human A2780Adr cells assessed as calcein-AM accumulation preincubated for 30 mins before calcein-AM addition measured up to 90 mins by fluorescence assay	[PMID: 23851114]
A549	IC₅₀	32.83 nM Compound: ANF	Reversal of DMBA-stimulated PTX resistance in human A549 cells assessed as PTX IC50 for inhibition of cell viability at 10 uM incubated for 36 hrs in presence of DMBA and PTX by MTT assay (Rvb = 119 +/-2.62 nM) Reversal of DMBA-stimulated PTX resistance in human A549 cells assessed as PTX IC50 for inhibition of cell viability at 10 uM incubated for 36 hrs in presence of DMBA and PTX by MTT assay (Rvb = 119 +/-2.62 nM)	[PMID: 38509663]
HEK293	EC₅₀	40 μM Compound: 4; ANF	Inhibition of human CYP1B1 expressed in HEK293 cells assessed as potentiation of cisplatin-induced cytotoxicity by measuring cisplatin EC50 at 0.016 uM by MTT assay (Rvb = 61 +/- 8 uM) Inhibition of human CYP1B1 expressed in HEK293 cells assessed as potentiation of cisplatin-induced cytotoxicity by measuring cisplatin EC50 at 0.016 uM by MTT assay (Rvb = 61 +/- 8 uM)	[PMID: 28222316]
HEK293	IC₅₀	>50 μM Compound: 4; ANF	Inhibition of human liver CYP1B1 expressed in HEK293 cells using 7-ethoxyresorufin as substrate preincubated for 30 mins followed by substrate addition measured after 60 mins by fluorescence assay Inhibition of human liver CYP1B1 expressed in HEK293 cells using 7-ethoxyresorufin as substrate preincubated for 30 mins followed by substrate addition measured after 60 mins by fluorescence assay	[PMID: 28222316]
HEK293	IC₅₀	>50 μM Compound: 4; ANF	Inhibition of human liver CYP1B1 expressed in HEK293 cells using CEC as substrate preincubated for 30 mins followed by substrate addition measured after 60 mins by fluorescence assay Inhibition of human liver CYP1B1 expressed in HEK293 cells using CEC as substrate preincubated for 30 mins followed by substrate addition measured after 60 mins by fluorescence assay	[PMID: 28222316]
HEK293	IC₅₀	>10000 nM Compound: 3; ANF	Inhibition of recombinant human liver CYP1B1 expressed in HEK293 cells using 7-ethoxyresorufin as substrate pretreated for 30 mins followed by substrate addition measured for 60 mins by EROD assay Inhibition of recombinant human liver CYP1B1 expressed in HEK293 cells using 7-ethoxyresorufin as substrate pretreated for 30 mins followed by substrate addition measured for 60 mins by EROD assay	[PMID: 28259840]
HEK293	IC₅₀	>10000 nM Compound: 3; ANF	Inhibition of recombinant human liver CYP1A1 expressed in HEK293 cells using 7-ethoxyresorufin as substrate pretreated for 30 mins followed by substrate addition measured for 60 mins by EROD assay Inhibition of recombinant human liver CYP1A1 expressed in HEK293 cells using 7-ethoxyresorufin as substrate pretreated for 30 mins followed by substrate addition measured for 60 mins by EROD assay	[PMID: 28259840]
HEK293	IC₅₀	>10 μM Compound: ANF	Inhibition of human CYP1A1 expressed in HEK293 cells using fluorogenic substrate 7-ethoxyresorufin as substrate preincubated for 30 mins followed by substrate addition measured for 60 mins by fluorescence assay Inhibition of human CYP1A1 expressed in HEK293 cells using fluorogenic substrate 7-ethoxyresorufin as substrate preincubated for 30 mins followed by substrate addition measured for 60 mins by fluorescence assay	[PMID: 28711350]
HEK293	IC₅₀	>10 μM Compound: ANF	Inhibition of human CYP1B1 expressed in HEK293 cells using fluorogenic 7-ethoxyresorufin as substrate preincubated for 30 mins followed by substrate addition measured for 60 mins by fluorescence assay Inhibition of human CYP1B1 expressed in HEK293 cells using fluorogenic 7-ethoxyresorufin as substrate preincubated for 30 mins followed by substrate addition measured for 60 mins by fluorescence assay	[PMID: 28711350]
HeLa	IC₅₀	4.98 μM Compound: 69	Inhibition of DNA dependent protein kinase isolated from HeLa cells Inhibition of DNA dependent protein kinase isolated from HeLa cells	[PMID: 15658870]
HepG2	IC₅₀	0.32 μM Compound: alpha-naphthoflavone	Inhibition of TCDD-induced EROD activity in human HepG2 cells after 24 hrs Inhibition of TCDD-induced EROD activity in human HepG2 cells after 24 hrs	[PMID: 15787451]
MCF7	IC₅₀	110.6 μM Compound: ANF	Inhibition of CYP1B1 in TCDD-stimulated human MCF7 cells assessed as inhibition of anticancer drug resistance by measuring docetaxel cytotoxic IC50 at 5 uM after 48 hrs by MTT assay (Rvb = 139.8 +/- 11.5 microM) Inhibition of CYP1B1 in TCDD-stimulated human MCF7 cells assessed as inhibition of anticancer drug resistance by measuring docetaxel cytotoxic IC50 at 5 uM after 48 hrs by MTT assay (Rvb = 139.8 +/- 11.5 microM)	[PMID: 25799264]
MCF7	IC₅₀	98.2 μM Compound: ANF	Inhibition of CYP1B1 in TCDD-stimulated human MCF7 cells assessed as inhibition of anticancer drug resistance by measuring docetaxel cytotoxic IC50 at 10 uM after 48 hrs by MTT assay (Rvb = 139.8 +/- 11.5 microM) Inhibition of CYP1B1 in TCDD-stimulated human MCF7 cells assessed as inhibition of anticancer drug resistance by measuring docetaxel cytotoxic IC50 at 10 uM after 48 hrs by MTT assay (Rvb = 139.8 +/- 11.5 microM)	[PMID: 25799264]
MCF7	EC₅₀	>20 μM Compound: ANF	Antiproliferative activity against human MCF-7 cells overexpressing CYP1A1 assessed as reduction in cell viability Antiproliferative activity against human MCF-7 cells overexpressing CYP1A1 assessed as reduction in cell viability	[PMID: 30448188]
MCF7	IC₅₀	>100 μM Compound: ANF	Cytotoxicity against drug-resistant TCCD-induced human MCF7 cells overexpressing CYP1B1 assessed as reduction in cell viability after 48 hrs by MTT assay Cytotoxicity against drug-resistant TCCD-induced human MCF7 cells overexpressing CYP1B1 assessed as reduction in cell viability after 48 hrs by MTT assay	[PMID: 31803401]
MCF7	IC₅₀	80.7 μM Compound: ANF	Cytotoxicity against human MCF7 cells assessed as reduction in cell viability after 48 hrs by MTT assay Cytotoxicity against human MCF7 cells assessed as reduction in cell viability after 48 hrs by MTT assay	[PMID: 31803401]
MDA-MB-231	IC₅₀	>100 μM Compound: ANF	Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability after 48 hrs by MTT assay Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability after 48 hrs by MTT assay	[PMID: 31803401]
MDCK-II	IC₅₀	1.31 μM Compound: 14	Inhibition of human BCRP expressed in MDCK2 cells assessed as accumulation of Hoechst 33342 preincubated for 30 mins before Hoechst 33342 addition measured after 120 mins by fluorescence assay Inhibition of human BCRP expressed in MDCK2 cells assessed as accumulation of Hoechst 33342 preincubated for 30 mins before Hoechst 33342 addition measured after 120 mins by fluorescence assay	[PMID: 23851114]
MDCK-II	IC₅₀	1.4 μM Compound: 14	Inhibition of human BCRP expressed in MDCK2 cells assessed as accumulation of pheophorbide-A preincubated for 30 mins before pheophorbide-A addition measured after 120 mins by flow cytometry Inhibition of human BCRP expressed in MDCK2 cells assessed as accumulation of pheophorbide-A preincubated for 30 mins before pheophorbide-A addition measured after 120 mins by flow cytometry	[PMID: 23851114]
NCI-H460	IC₅₀	481.4 nM Compound: ANF	Synergistic anti-cancer activity of human PTX-resistant NCI-H460 cells assessed as PTX IC50 at 5 uM incubated for 48 hrs in presence of PTX by CCK8 assay Synergistic anti-cancer activity of human PTX-resistant NCI-H460 cells assessed as PTX IC50 at 5 uM incubated for 48 hrs in presence of PTX by CCK8 assay	[PMID: 38692523]

In Vitro

Alpha-Naphthoflavone (0.01-100 μM, 5 min) induces vascular relaxation by inducing extracellular calcium inflow and NO formation^[2].
Alpha-Naphthoflavone (0.01-100 μM, 48 h) can inhibit HeLa cell proliferation, block the G1/S phase, and increase p53 level and apoptosis^[3].
Alpha-Naphthoflavone (5, 10, 20, 40 μM, 24 h) can protect HepG2 hepatocytes treated with oleic acid (OA)^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Proliferation Assay^[3]

Cell Line:

HeLa
Concentration:

0.01, 1, 10, 100 μM
Incubation Time:

6 days
Result:

Decreased cell proliferation in a dose-dependent manner with IC₅₀ value of 36.81 μM.

Apoptosis Analysis^[3]

Cell Line:

HeLa
Concentration:

50 μM
Incubation Time:

12, 24, 36 h
Result:

Induced a mild but significant apoptosis rate.

Western Blot Analysis^[3]

Cell Line:

HeLa
Concentration:

50 μM
Incubation Time:

12, 24, 36 h
Result:

Increased the level of p53 at 12 h.

In Vivo

Alpha-Naphthoflavone (80, 160 mg/kg/day, gavage for 4 weeks) has protective effects on NAFLD mice induced by high-fat diet (HFD)^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

HFD-induced mice model^[4]
Dosage:

80, 160 mg/kg
Administration:

i.g.
Result:

Decreased the levels of AST, TG and TC.

Chemical Information

CAS No. 604-59-1
Appearance Solid
Molecular Weight 272.30
Formula C₁₉H₁₂O₂
Color White to light yellow
SMILES

O=C1C=C(C2=CC=CC=C2)OC3=C1C=CC4=CC=CC=C43
Structure Classification
- Flavonoids
- Flavones
Initial Source
- Plants
- Compositae
Shipping

Room temperature in continental US; may vary elsewhere.
Storage

4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Publications (10)

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Phytomedicine

Effect of allyl isothiocyanate on oxidative stress in COPD via the AhR / CYP1A1 and Nrf2 / NQO1 pathways and the underlying mechanism. [Abstract]

2023 Jun:114:154774. PMID: 36996530
J Hazard Mater

Stereostructure-activity mechanism of cyproconazole by cytochrome P450 in rat liver microsomes: A combined experimental and computational study. [Abstract]

2021 Aug 15:416:125764. PMID: 33827004
Cell Rep

Aryl hydrocarbon receptor-induced activation of AIM2 inflammasome is mediated by MOMP and MPT: A vital therapeutic pathway for inflammation. [Abstract]

2025 Dec 10;44(12):116673. PMID: 41385364
Environ Pollut

Enantioselective metabolic mechanism and metabolism pathway of tetraconazole in human liver microsomes: In vitro and in silico study. [Abstract]

2026 May 1:396:127849. PMID: 41720237
Environ Pollut

Assessing environmental and human health risks: Insight from the enantioselective metabolism and degradation of fenpropidin. [Abstract]

2024 May 25:124214. PMID: 38801883
Pharmaceutics

Plasma Protein Binding, Biostability, Metabolite Profiling, and CYP450 Phenotype of TPB15 Across Different Species: A Novel Smoothened Inhibitor for TNBC Therapy. [Abstract]

2025 Mar 26;17(4):423. PMID: 40284418
J Agric Food Chem

Enantioselective Metabolic Mechanism and Metabolism Pathway of Pydiflumetofen in Rat Liver Microsomes: In Vitro and In Silico Study. [Abstract]

2022 Mar 2;70(8):2520-2528. PMID: 35184556
Ecotoxicol Environ Saf

Aristolochic acid-induced dyslipidemia and hepatotoxicity: The potential role of FXR and AHR receptors. [Abstract]

2024 Nov 5:287:117266. PMID: 39509784
AAPS J

Cannabinoid Interactions with Cytochrome P450 Drug Metabolism: a Full-Spectrum Characterization. [Abstract]

2021 Jun 28;23(4):91. PMID: 34181150
Research Square Preprint

2023 Oct 28.

Solvent & Solubility

In Vitro:

DMSO : 25 mg/mL (91.81 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

3.6724 mL

18.3621 mL

36.7242 mL

5 mM

0.7345 mL

3.6724 mL

7.3448 mL

10 mM

0.3672 mL

1.8362 mL

3.6724 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Molarity Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

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Purity & Documentation

Select Batch:

Purity: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (283 KB)
SDS (392 KB)
- English - EN (392 KB)
- Français - FR (392 KB)
- Deutsch - DE (392 KB)
- Norwegian - NO (392 KB)
- Español - ES (392 KB)
- Swedish - SV (392 KB)
- Italian - IT (392 KB)
- Korean - KR (392 KB)
- Portuguese - PT (392 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

References

[1]. Campbell DR, et al. Flavonoid inhibition of aromatase enzyme activity in human preadipocytes. J Steroid Biochem Mol Biol. 1993 Sep;46(3):381-8. [Content Brief]

[2]. Cheng YW, et al. Alpha-naphthoflavone induces vasorelaxation through the induction of extracellular calcium influx and NO formation in endothelium. Naunyn Schmiedebergs Arch Pharmacol. 2003 Nov;368(5):377-85. [Content Brief]

[3]. Flores-Pérez A, et al. Apoptosis induction and inhibition of HeLa cell proliferation by alpha-naphthoflavone and resveratrol are aryl hydrocarbon receptor-independent. Chem Biol Interact. 2018 Feb 1;281:98-105. [Content Brief]

[4]. Xia H, et al. Alpha-naphthoflavone attenuates non-alcoholic fatty liver disease in oleic acid-treated HepG2 hepatocytes and in high fat diet-fed mice. Biomed Pharmacother. 2019 Oct;118:109287. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	3.6724 mL	18.3621 mL	36.7242 mL	91.8105 mL
	5 mM	0.7345 mL	3.6724 mL	7.3448 mL	18.3621 mL
	10 mM	0.3672 mL	1.8362 mL	3.6724 mL	9.1811 mL
	15 mM	0.2448 mL	1.2241 mL	2.4483 mL	6.1207 mL
	20 mM	0.1836 mL	0.9181 mL	1.8362 mL	4.5905 mL
	25 mM	0.1469 mL	0.7345 mL	1.4690 mL	3.6724 mL
	30 mM	0.1224 mL	0.6121 mL	1.2241 mL	3.0604 mL
	40 mM	0.0918 mL	0.4591 mL	0.9181 mL	2.2953 mL
	50 mM	0.0734 mL	0.3672 mL	0.7345 mL	1.8362 mL
	60 mM	0.0612 mL	0.3060 mL	0.6121 mL	1.5302 mL
	80 mM	0.0459 mL	0.2295 mL	0.4591 mL	1.1476 mL

Keywords

Alpha-Naphthoflavone

10 Cited Publications

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Alpha-Naphthoflavone

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Publications Citing Use of MedChemExpress (MCE) Alpha-Naphthoflavone

All Cytochrome P450 Isoforms

Biological Activity

Chemical Information

Publications (10)

Solvent & Solubility

Purity & Documentation

References

Help & FAQs

Complete Stock Solution Preparation Table

Alpha-Naphthoflavone Related Classifications

HY-125833 Related Classifications