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M1404

Sigma-Aldrich

Nocodazole

≥99% (TLC), powder

Synonym(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

Empirical Formula (Hill Notation):
C14H11N3O3S
CAS Number:
31430-18-9
Molecular Weight:
301.32
Beilstein:
1085978
EC Number:
250-626-5
MDL number:
MFCD00005588
UNSPSC Code:
12352200
PubChem Substance ID:
24278535
NACRES:
NA.77

Quality Level

300

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

SMILES string

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

Gene Information

human ... TUBB(203068)

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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.

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.

Physical form

Color white to faint yellow and pink

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H341,H361d

Hazard Classifications

Muta. 2 - Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
Therese Wilhelm et al.
Nature communications, 10(1), 3585-3585 (2019-08-10)
Replication stress, a hallmark of cancerous and pre-cancerous lesions, is linked to structural chromosomal aberrations. Recent studies demonstrated that it could also lead to numerical chromosomal instability (CIN). The mechanism, however, remains elusive. Here, we show that inducing replication stress
Shunsuke Ishii et al.
Scientific reports, 9(1), 11635-11635 (2019-08-14)
Lysosomes are largely responsible for significant degradation of intracellular and extracellular proteins via the secretory pathway, autophagy, and endocytosis. Therefore, dysregulation of lysosomal homeostasis influences diverse cellular functions. However, a straightforward and quantitative method to measure the integrity of the
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