| CAS NO: | 604-59-1 |
| 包装 | 价格(元) |
| 10g | 电议 |
| 25g | 电议 |
| Storage | Store at -20°C |
| M.Wt | 272.3 |
| Cas No. | 604-59-1 |
| Formula | C19H12O2 |
| Synonyms | 7,8-Benzoflavone,NSC 407011 |
| Solubility | insoluble in EtOH; insoluble in H2O; ≥10 mg/mL in DMSO |
| Chemical Name | 2-phenyl-4H-naphtho[1,2-b]pyran-4-one |
| Canonical SMILES | O=C1C2=C(C(C=CC=C3)=C3C=C2)OC(C4=CC=CC=C4)=C1 |
| 运输条件 | 蓝冰运输或根据您的需求运输。 |
| 一般建议 | 为了使其更好的溶解，请用37℃加热试管并在超声波水浴中震动片刻。不同厂家不同批次产品溶解度各有差异，仅做参考。若实验所需浓度过大至产品溶解极限，请添加助溶剂助溶或自行调整浓度。溶液形式一般不宜长期储存，请尽快用完。 |
α-Naphthoflavone (α-NF), also known as 7,8-benzoflavone and 2-phenyl-benzo(h)chromen-4-one, is a synthetic flavone derivative. α-Naphthoflavone is a potent inhibitor of the enzyme aromatase, which implicated in converting testosterone to estrogen [1]. It can be prepared from 2-naphthol and cinnamaldehyde [2]. α-naphthoflavone functions as both an Ah receptor antagonist and an inhibitor of cytochrome P450 activity. α-naphthoflavone stimulated P450 3A4 by selectively binding and activating an otherwise inactive subpopulation of this P450 and promoting benzo[a]pyrene binding to the latter [3].
In vitro: α-NF inhibited microsomal rabbit CYP3A6 and human CYP3A4 irreversibly. α-NF and β-NF strongly inhibited CYP1A-mediated ethoxyresorufin O-deethylase (EROD) activity with the Ki value of 9.1 ± 0.8 and 7.6 ± 1.1 nM, respectively. α-NF at 0.5, 5, 50 and 500 μM inhibited liver microsome-catalyzed AFB1-DNA binding by 22, 58, 84 and 91%, respectively [4].
In vivo: α-NF inhibited CYP1A enzymes and caused both synergism and antagonism of retene toxicity to rainbow trout (Oncorhynchus mykiss) [5]. In male Sprague–Dawley rats, treatment with αNF had no significant effects on body mass after 5 days and caused only minor increases of liver, kidney, and heart CYP1A1 mRNA. In contrast, lung CYP1A1 mRNA was increased by αNF treatment to levels comparable to that seen with β-NF treatment [6].
References:
[1]. Campbell D R, Kurzer M S. Flavonoid inhibition of aromatase enzyme activity in human preadipocytes[J]. The Journal of steroid biochemistry and molecular biology, 1993, 46(3): 381-388.
[2]. Harvey R G, HAHN J T A I, Bukowska M, et al. A new chromone and flavone synthesis and its utilization for the synthesis of potentially antitumorigenic polycyclic chromones and flavones[J]. Journal of organic chemistry, 1990, 55(25): 6161-6166.
[3]. Koley A P, Buters J T M, Robinson R C, et al. Differential mechanisms of cytochrome P450 inhibition and activation by α-naphthoflavone[J]. Journal of Biological Chemistry, 1997, 272(6): 3149-3152.
[4]. Takahashi N, Miranda C L, Henderson M C, et al. Inhibition of in vitro aflatoxin B1-DNA binding in rainbow trout by CYP1A inhibitors: α-naphthoflavone, β-naphthoflavone and trout CYP1A1 peptide antibody[J]. Comparative Biochemistry and Physiology Part C: Pharmacology, Toxicology and Endocrinology, 1995, 110(3): 273-280.
[5]. Hodson P V, Qureshi K, Noble C A J, et al. Inhibition of CYP1A enzymes by α-naphthoflavone causes both synergism and antagonism of retene toxicity to rainbow trout (Oncorhynchus mykiss)[J]. Aquatic toxicology, 2007, 81(3): 275-285.
[6]. Sinal C J, Webb C D, Bend J R. Differential in vivo effects of α‐
aphthoflavone and β‐
aphthoflavone on CYP1A1 and CYP2E1 in rat liver, lung, heart, and kidney[J]. Journal of biochemical and molecular toxicology, 1999, 13(1): 29-40.
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