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M1404

Sigma-Aldrich

诺考达唑

≥99% (TLC), powder

别名:

R 17934, 甲基-(5-噻吩甲酰-2-苯并咪唑基)氨基甲酸, 甲基N(5-噻吩甲酰-2-苯并咪唑基)氨基甲酸, 诺考达唑

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About This Item

经验公式（希尔记法）:
C14H11N3O3S
CAS号:
31430-18-9
分子量:
301.32
Beilstein:
1085978
EC 号:
250-626-5
MDL编号:
MFCD00005588
UNSPSC代码:
12352200
PubChem化学物质编号:
24278535
NACRES:
NA.77

质量水平

300

方案

≥99% (TLC)

表单

powder

mp

300 °C (dec.)

溶解性

DMSO: soluble 10 mg/mL (may require heating)
H2O: insoluble

储存温度

2-8°C

SMILES字符串

COC(=O)Nc1nc2cc(ccc2[nH]1)C(=O)c3cccs3

InChI

1S/C14H11N3O3S/c1-20-14(19)17-13-15-9-5-4-8(7-10(9)16-13)12(18)11-3-2-6-21-11/h2-7H,1H3,(H2,15,16,17,19)

InChI key

KYRVNWMVYQXFEU-UHFFFAOYSA-N

基因信息

human ... TUBB(203068)

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一般描述

Nocodazole (NZO) is an experimental benzimidazole-based agent that targets both protein kinases and microtubules. It serves as a lead compound in the quest for new colchicine binding site inhibitors (CBSIs). This co-crystallized ligand acts as a high-affinity ligand for cancer-related kinases ABL, c-KIT, BRAF, and MEK, and functions as a rapidly-reversible inhibitor of microtubule polymerization.

应用

Nocodazole has been used to induce microtubule depolymerization in mouse melanoma B16-F1 cells. It has also been used to treat A549 cells for mitotic arrest.

生化/生理作用

诺考达唑(Nocodazole)是一种抗有丝分裂剂，通过结合β−−微管蛋白，阻止两对链间二硫键之一的形成，进而抑制微管动力学、破坏有丝分裂纺锤体功能和片段化高尔基复合体来解聚微管。诺考达唑将细胞周期阻滞在G2/M期，也阻止T细胞抗原受体的磷酸化并抑制其活性。在一些正常和肿瘤细胞系中，诺考达唑刺激微管蛋白内在GTP酶活性，激活JNK/SAPK信号传导通路和诱导凋亡。诺考达唑增强CRISPR同源重组修复(HDR)效率和加强Cas9介导的编辑频率。

外形

颜色从白色到淡黄色和粉红色

象形图

Health hazard
GHS08

警示用语：

Warning

危险声明

H341,H361d

危险分类

Muta. 2 - Repr. 2

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

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分析证书(COA)

Lot/Batch Number
0000185274
0000152859
0000369406
0000349966
0000347109

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Microtubule dynamics alter the interphase nucleus
Gerlitz G, et al.
Cellular and Molecular Life Sciences, 70, 1255-1268 (2013)
Muralidharan Mani et al.
Biochimica et biophysica acta. Molecular cell research, 1866(9), 1463-1474 (2019-06-15)
The perinuclear stacks of the Golgi apparatus maintained by dynamic microtubules are essential for cell migration. Activation of Akt (protein kinase B, PKB) negatively regulates glycogen synthase kinase 3β (GSK3β)-mediated tau phosphorylation, which enhances tau binding to microtubules and microtubule
Revisiting activity of some nocodazole analogues as a potential anticancer drugs using molecular docking and DFT calculations
Khattab M and Al-Karmalawy AA
Frontiers in Chemistry, 9, 628398-628398 (2021)
Alessandra Pisciottani et al.
Cells, 8(7) (2019-07-10)
Abscission is the final step of cell division, mediating the physical separation of the two daughter cells. A key player in this process is the microtubule-severing enzyme spastin that localizes at the midbody where its activity is crucial to cut
Yuan He et al.
Journal of virology, 84(24), 12832-12840 (2010-09-24)
Many viruses interact with the host cell division cycle to favor their own growth. In this study, we examined the ability of influenza A virus to manipulate cell cycle progression. Our results show that influenza A virus A/WSN/33 (H1N1) replication
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