反-查耳酮

反-查耳酮用途

trans-Chalcone 是从Aronia melanocarpa 果皮中分离出来的,是类黄酮前体的双酚核心结构。trans-Chalcone 是有效的脂肪酸合酶 (FAS) 和 α-淀粉酶 (b>α-amylase) 抑制剂。trans-Chalcone 引起细胞周期停滞并诱导乳腺癌细胞系 MCF-7 凋亡。trans-Chalcone 具有抗真菌和抗癌活性。

反-查耳酮名称

[ CAS 号 ]:
614-47-1

[ 中文名 ]:
反式-查耳酮

[ 英文名 ]:
(E)-Chalcone

[中文别名 ]:

[英文别名 ]:

Phenyl (E)-2-phenylethenyl ketone
RV1U1R &&E Form
Phenyl styryl ketone
2-Propen-1-one, 1,3-diphenyl-, (E)-
a-Benzylideneacetophenone
b-Phenylacrylophenone
β-Phenylacrylophenone
1-Benzoyl-2-phenylethylene
chalcone
trans-benzylideneacetophenone

反-查耳酮生物活性

[ 描述 ]:

[ 相关类别 ]:

信号通路 >> 细胞凋亡 >> 细胞凋亡

研究领域 >> 癌症

信号通路 >> 代谢酶/蛋白酶 >> 脂肪酸合成酶(FAS)

信号通路 >> 抗感染 >> 真菌

研究领域 >> 炎症/免疫

[体外研究]

反式查尔酮竞争性抑制猪胰腺癌α-Ki为48的淀粉酶μM[2]。反式查尔酮(30.23-98.03μ米；24小时)诱导MCF-7细胞周期阻滞和凋亡[1]。反式查尔酮(30.23-98.03μ米；24小时)降低凋亡相关蛋白Bcl-2的表达并诱导CIDEA基因的表达[1]。反式查尔酮(58.25μ米；6,24小时)对Bcl-2有较强的抑制作用,对APAF1和BAX有较强的诱导作用,对CIDEA有较强的诱导作用[1]。反式查尔酮(24小时)抑制MCF-7细胞活力(IC20=30.23)μ米；IC50=58.25μ米；IC80=98.03μM) 是的。反式查尔酮(48h)的IC50s为41.53μM和48.41μM分别用于MCF-7和3T3细胞系。反式查尔酮具有明显的细胞毒性活性[1]。凋亡分析[1]细胞系：MCF-7细胞浓度：30.23、58.25、98.03μ结果：诱导乳腺癌细胞株凋亡。细胞周期分析[1]细胞系：MCF-7细胞浓度：30.23、58.25、98.03μM孵育时间：24小时结果：导致细胞周期阻滞于G1期。westernblot分析[1]细胞系：MCF-7细胞浓度：20,40,80μ结果：降低凋亡相关蛋白Bcl-2的表达,诱导CIDEA基因的表达。细胞周期蛋白D1在48h出现明显降解。RT-PCR[1]细胞系：MCF-7细胞浓度：58.25μ结果：24小时内对Bcl-2有较强的抑制作用,对APAF1和BAX有较强的诱导作用,对CIDEA有较强的诱导作用。

[参考文献]

[1]. Luis Felipe Buso Bortolotto, et al. Cytotoxicity of trans-chalcone and licochalcone A against breast cancer cells is due to apoptosis induction and cell cycle arrest. Biomed Pharmacother. 2017 Jan;85:425-433.

[2]. Mahmoud Najafian, et al. Trans-chalcone: a novel small molecule inhibitor of mammalian alpha-amylase. Mol Biol Rep. 2011 Mar;38(3):1617-20.

[3]. Tamires Aparecida Bitencourt, et al. Trans-chalcone and quercetin down-regulate fatty acid synthase gene expression and reduce ergosterol content in the human pathogenic dermatophyte Trichophyton rubrum. BMC Complement Altern Med. 2013 Sep 17;13:229.

反-查耳酮物理化学性质

[ 密度 ]:
1.1±0.1 g/cm3

[ 沸点 ]:
346.6±25.0 °C at 760 mmHg

[ 熔点 ]:
55-57ºC

[ 分子式 ]:
C₁₅H₁₂O

[ 分子量 ]:
208.255

[ 闪点 ]:
150.1±18.1 °C

[ 精确质量 ]:
208.088821

[ PSA ]:
17.07000

[ LogP ]:
4.01

[ 蒸汽压 ]:
0.0±0.8 mmHg at 25°C

[ 折射率 ]:
1.625

[ 储存条件 ]:
室温，密封

反-查耳酮MSDS

详细MSDS(安全技术说明书)

反-查耳酮安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H302-H319-H335

[ 警示性声明 ]:
P261-P305 + P351 + P338

[ 个人防护装备 ]:
dust mask type N95 (US);Eyeshields;Gloves

[ 危害码 (欧洲) ]:
Xn:Harmful;

[ 风险声明 (欧洲) ]:
R22;R36/37

[ 安全声明 (欧洲) ]:
S22-S36/37/39-S45

[ 危险品运输编码 ]:
NONH for all modes of transport

[ WGK德国 ]:
3

[ RTECS号 ]:
UD5576750

反-查耳酮合成路线

详细合成路线

反-查耳酮上下游产品

反-查耳酮上游产品

反-查耳酮下游产品

反-查耳酮文献

Impact of induced fit on ligand binding to the androgen receptor: a multidimensional QSAR study to predict endocrine-disrupting effects of environmental chemicals.

J. Med. Chem. 48 , 5666-74, (2005)

We investigated the influence of induced fit of the androgen receptor binding pocket on free energies of ligand binding. On the basis of a novel alignment procedure using flexible docking, molecular d...

A chemical screening approach reveals that indole fluorescence is quenched by pre-fibrillar but not fibrillar amyloid-beta.

Bioorg. Med. Chem. Lett. 19 , 4952-7, (2009)

Aggregated amyloid-beta (Abeta) peptide is implicated in the pathology of Alzheimer's disease. In vitro and in vivo, these aggregates are found in a variety of morphologies, including globular oligome...

Novel chalcone derivatives as potent Nrf2 activators in mice and human lung epithelial cells.

J. Med. Chem. 54 , 4147-59, (2011)

Nrf2-mediated activation of antioxidant response element is a central part of molecular mechanisms governing the protective function of phase II detoxification and antioxidant enzymes against carcinog...

更多文献