金黄三羧酸

金黄三羧酸用途

Aurintricarboxylic acid 是高效的,αβ- 亚甲基 -ATP 敏感选择性 P2X1Rs 和 P2X3Rs 变构拮抗剂,对 rP2X1R 和 rP2X3R 作用的 IC50 值分别为 8.6 nM 和 72.9 nM。Aurintricarboxylic acid 是一种有效的抗流感剂,通过直接抑制神经氨酸酶 (neuraminidase) 作用。Aurintricarboxylic acid 也是拓扑异构酶 II 和凋亡抑制剂。Aurintricarboxylic acid 是选择性的 TWEAK-Fn14 信号通路抑制剂。

金黄三羧酸名称

[ CAS 号 ]:
4431-00-9

[ 中文名 ]:
金精三羧酸

[ 英文名 ]:
Aurintricarboxylic acid

[中文别名 ]:

[英文别名 ]:

Aurintricarboxylic acid
EINECS 224-628-1
MFCD00011663

金黄三羧酸生物活性

[ 描述 ]:

[ 相关类别 ]:

信号通路 >> 抗感染 >> 流感病毒

信号通路 >> 细胞周期/DNA损伤 >> 拓扑异构酶

研究领域 >> 感染

研究领域 >> 炎症/免疫

信号通路 >> 跨膜转运 >> P2X受体

研究领域 >> 神经疾病

[ 靶点 ]

Topoisomerase II

rP2X1R:8.6 nM (IC50)

rP2X3R:72.9 nM (IC50)

Apoptosis

[体外研究]

金杂羧酸对rP2X1Rs和rP2X3Rs有较强的抑制作用,IC50值分别为8.6nm和72.9nm,对P2X2/3Rs、P2X2Rs、P2X4Rs或P2X7Rs的抑制作用较弱[1]。金丝桃酸对ATP诱导电流的抑制作用是浓度依赖性的[1]。金丝桃酸是P2X3R的非竞争性拮抗剂[1]。金丝桃酸能抑制严重急性呼吸综合征相关冠状病毒(SARS-CoV)和痘苗病毒[2]。金丝桃酸保护MDCK细胞免受甲型流感病毒PR8、NY或N感染[2]。金丝桃酸抑制甲型和乙型流感病毒的复制[2]。金丝桃酸抑制甲型和乙型流感病毒神经氨酸酶活性[2]。金丝桃酸抑制TWEAK-Fn14介导的NF-κB活化[4]。金杂羧酸(10μM；0.5-2小时)抑制GBM细胞中TWEAK-Fn14介导的NF-κB、Akt和Src磷酸化[4]。金丝桃酸阻断神经胶质瘤细胞中刺激的Rac1激活和TRAF2向Fn14胞质域的募集[4]。金丝桃酸抑制TWEAK刺激的胶质瘤细胞迁移和侵袭而不引起细胞毒性[4]。Western Blot分析[4]细胞株：T98G,A172,GBM44胶质瘤细胞浓度：10μM孵育时间：0.5小时,1小时,2小时结果：三种GBM细胞株中NF-κB家族成员p65,Akt,Src磷酸化等下游信号的激活均被阻断。

[参考文献]

[1]. Obrecht AS, et al. Identification of aurintricarboxylic acid as a potent allosteric antagonist of P2X1 and P2X3 receptors. Neuropharmacology. 2019 Nov 1;158:107749.

[2]. Hashem AM, et al. Aurintricarboxylic acid is a potent inhibitor of influenza A and B virus neuraminidases. PLoS One. 2009 Dec 17;4(12):e8350.

[3]. Benchokroun Y, et al. Aurintricarboxylic acid, a putative inhibitor of apoptosis, is a potent inhibitor of DNA topoisomerase II in vitro and in Chinese hamster fibrosarcoma cells. Biochem Pharmacol. 1995 Jan 31;49(3):305-13.

[4]. Benchokroun Y, et al. Aurintricarboxylic acid, a putative inhibitor of apoptosis, is a potent inhibitor of DNA topoisomerase II in vitro and in Chinese hamster fibrosarcoma cells. Biochem Pharmacol. 1995 Jan 31;49(3):305-13.

金黄三羧酸物理化学性质

[ 密度 ]:
1.6±0.1 g/cm3

[ 沸点 ]:
759.6±60.0 °C at 760 mmHg

[ 熔点 ]:
300 °C(lit.)

[ 分子式 ]:
C₂₂H₁₄O₉

[ 分子量 ]:
422.341

[ 闪点 ]:
427.1±29.4 °C

[ 精确质量 ]:
422.063782

[ PSA ]:
169.43000

[ LogP ]:
4.09

[ 外观性状 ]:
powder | dark red to brown

[ 蒸汽压 ]:
0.0±2.7 mmHg at 25°C

[ 折射率 ]:
1.751

[ 储存条件 ]:
室温

[ 水溶解性 ]:
1 M NH4OH: 10 mg/mL

金黄三羧酸MSDS

详细MSDS(安全技术说明书)

金黄三羧酸毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GU4790000

CHEMICAL NAME :: 1,4-Cyclohexadiene-1-carboxylic acid, 3-(bis(3-carboxy-4-hydroxyphenyl)methylene)-6-oxo-

CAS REGISTRY NUMBER :: 4431-00-9

BEILSTEIN REFERENCE NO. :: 2228904

LAST UPDATED :: 199701

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C22-H14-O9

MOLECULAR WEIGHT :: 422.36

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 340 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 558 mg/kg/18D-I

TOXIC EFFECTS :: Related to Chronic Data - death

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Rodent - mouse Liver

DOSE/DURATION :: 100 umol/L

REFERENCE :: AMOKAG Acta Medicia Okayama. (Okayama Univ. Medical School, Okayama, Japan) V.27 1973- Volume(issue)/page/year: 33,149,1979

金黄三羧酸安全信息

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

[ 危害码 (欧洲) ]:
Xi: Irritant;

[ 风险声明 (欧洲) ]:
36/37/38

[ 安全声明 (欧洲) ]:
S26-S36

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

[ WGK德国 ]:
3

[ RTECS号 ]:
GU4790000

金黄三羧酸制备

水杨酸与甲醛反应得到亚甲基二水杨酸，再将其与水杨酸、亚硝酰硫酯混合反应，得金黄三羧酸。

金黄三羧酸文献

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Pflugers Arch. 467(2) , 389-98, (2015)

Skeletal muscles contain several subtypes of myofibers that differ in contractile and metabolic properties. Transcriptional control of fiber-type specification and adaptation has been intensively inve...

Chemical genetics reveals a complex functional ground state of neural stem cells.

Nat. Chem. Biol. 3(5) , 268-273, (2007)

The identification of self-renewing and multipotent neural stem cells (NSCs) in the mammalian brain holds promise for the treatment of neurological diseases and has yielded new insight into brain canc...

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