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Merck
CN
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文件

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

检测方案

≥99% (TLC)

形式

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

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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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
Microtubule dynamics alter the interphase nucleus
Gerlitz G, et al.
Cellular and Molecular Life Sciences, 70, 1255-1268 (2013)
Yuxi Wang et al.
The FEBS journal, 283(1), 102-111 (2015-10-16)
Microtubules are dynamic assemblies of αβ-tubulin heterodimers and have been recognized as highly attractive targets for cancer chemotherapy. A broad range of agents bind to tubulin and interfere with microtubule assembly. Despite having a long history of characterization, colchicine binding
Yuanming Cheng et al.
Cell reports, 28(7), 1703-1716 (2019-08-15)
Stem cells balance cellular fates through asymmetric and symmetric divisions in order to self-renew or to generate downstream progenitors. Symmetric commitment divisions in stem cells are required for rapid regeneration during tissue damage and stress. The control of symmetric commitment remains
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)
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