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Merck

M1404

Nocodazole

≥99% (TLC), Microtubule inhibitor, powder

Synonyme(s) :

Methyl N-(5-thenoyl-2-benzimidazolyl)carbamate, Methyl [5-(2-thienylcarbonyl)-1H-benzimidazol-2-yl]carbamate, Oncodazole, R 17934, [5-(2-Thienylcarbonyl)-1H-benzimidazol-2-yl]-carbamic acid methyl ester

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About This Item

Formule empirique (notation de Hill) :
C14H11N3O3S
Numéro CAS:
Poids moléculaire :
301.32
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
250-626-5
MDL number:
Beilstein/REAXYS Number:
1085978

Nom du produit

Nocodazole, ≥99% (TLC), powder

InChI key

KYRVNWMVYQXFEU-UHFFFAOYSA-N

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)

SMILES string

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

assay

≥99% (TLC)

form

powder

mp

300 °C (dec.)

solubility

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

storage temp.

2-8°C

Quality Level

Gene Information

human ... TUBB(203068)

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Application

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.

Biochem/physiol Actions

Nocodazole is an antimitotic agent that disrupts microtubules by binding to β−tubulin and preventing formation of one of the two interchain disulfide linkages, thus inhibiting microtubule dynamics, disruption of mitotic spindle function, and fragmentation of the Golgi complex. Nocodazole arrests the cell cycle at G2/M phase and also prevents phosphorylation of the T cell antigen receptor and inhibits its activity. Nocodazole stimulates the intrinsic GTPase activity of tubulin and activates the JNK/SAPK signaling pathway and induces apoptosis in several normal and tumor cell lines. Nocodazole has been shown to enhance CRISPR homology-directed repair (HDR) efficiency and increase Cas9-mediated editing frequencies.

General description

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.

Physical form

Color white to faint yellow and pink

pictograms

Health hazard

signalword

Warning

Hazard Classifications

Muta. 2 - Repr. 2

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Consulter la Bibliothèque de documents

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)
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
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
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

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