287897
双羟香豆素
A cell-permeable quinone reductase inhibitor with anticoagulant properties.
别名:
双羟香豆素, 3，3ʹ-亚甲基双（4-羟基香豆素），双羟基香豆素，双香豆酚
产品名称
双羟香豆素, A cell-permeable quinone reductase inhibitor with anticoagulant properties.
SMILES string
[o]1c2c(c(c([c]1=O)Cc3[c]([o]c4c(c3O)cccc4)=O)O)cccc2
InChI
1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2
InChI key
DOBMPNYZJYQDGZ-UHFFFAOYSA-N
description
Merck USA index - 14, 3090
assay
≥98% (titration)
form
solid
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze
protect from light
color
white
solubility
0.1 M NaOH: 15 mg/mL
pyridine: 50 mg/mL
shipped in
ambient
storage temp.
2-8°C
Quality Level
相关类别
Biochem/physiol Actions
主要靶标
在体外阻断布雷菲德菌素A依赖性单ADP-核糖基化
在体外阻断布雷菲德菌素A依赖性单ADP-核糖基化
产物不与ATP竞争。
可逆：否
细胞可渗透性：是
靶标IC50：180 µM和150 µM，分别用于阻断体外布雷菲德菌素A依赖的单ADP-核糖基化和活细胞中高尔基体的分解。
Disclaimer
毒性：有毒 & 致癌/致畸性（G）
General description
一种具有抗凝血特性的细胞渗透性醌还原酶抑制剂。与NADH或NADPH竞争性结合以抑制NAD(P)H:醌氧化还原酶（NQO1）。显示抑制IGF-I，甲萘醌和DMNQ介导的应激激活的蛋白激酶/c-Jun NH2末端激酶（SAPK/JNK）的激活以及随后c-Jun的磷酸化以及应激诱导的SAPK/JNK的激活（高渗山梨糖醇）。不会影响p38的磷酸化或蛋白激酶B（AKT）激活。还显示在MCF7乳腺癌细胞中诱导凋亡。在体外和MCF7/VPα细胞（用GST A1-1转染的MCF7的多药耐药性衍生物）中抑制谷胱甘肽S转移酶(GST)A1-1酶（Kiu = 4.4 µM，Kic = 3.6 µM）。阻断体外布雷菲德菌素A依赖的单ADP-核糖基化和活细胞中高尔基体的分解（IC50分别为180 µM 和150 µM）。
Other Notes
Seanor, K.L., et al. 2003.Antioxid.Redox.Signal5, 103.
Krause, D., et al. 2001.J. Biol. Chem.276, 19244.
Pink, J.J., et al. 2000.J. Biol. Chem.275, 5416.
Cross, J.V., et al. 1999.J. Biol. Chem.274, 31150.
Morrow, C.S., et al. 1998.J. Biol. Chem.273, 20114.
Weigert, R., et al. 1997.J. Biol. Chem.272, 14200.
Krause, D., et al. 2001.J. Biol. Chem.276, 19244.
Pink, J.J., et al. 2000.J. Biol. Chem.275, 5416.
Cross, J.V., et al. 1999.J. Biol. Chem.274, 31150.
Morrow, C.S., et al. 1998.J. Biol. Chem.273, 20114.
Weigert, R., et al. 1997.J. Biol. Chem.272, 14200.
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Packaging
用惰性气体包装
Preparation Note
溶液中不稳定；仅在使用前进行复溶。
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Oral - Aquatic Chronic 2 - STOT RE 1 Oral
存储类别
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Tatiana A Giovannucci et al.
Cell death & disease, 12(10), 914-914 (2021-10-08)
Malignant cells display an increased sensitivity towards drugs that reduce the function of the ubiquitin-proteasome system (UPS), which is the primary proteolytic system for destruction of aberrant proteins. Here, we report on the discovery of the bioactivatable compound CBK77, which
Hong-Zhong Zhou et al.
Cell communication and signaling : CCS, 17(1), 168-168 (2019-12-18)
Our previous study has demonstrated that NAD(P)H: quinone oxidoreductase 1 (NQO1) is significantly upregulated in human liver cancer where it potentiates the apoptosis evasion of liver cancer cell. However, the underlying mechanisms of the oncogenic function of NQO1 in HCC
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