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M1404

Sigma-Aldrich

Nocodazole

≥99% (TLC), powder

Sinônimo(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

Fórmula empírica (Notação de Hill):
C14H11N3O3S
Número CAS:
31430-18-9
Peso molecular:
301.32
Beilstein:
1085978
Número CE:
250-626-5
Número MDL:
MFCD00005588
Código UNSPSC:
12352200
ID de substância PubChem:
24278535
NACRES:
NA.77

Nível de qualidade

300

Ensaio

≥99% (TLC)

forma

powder

pf

300 °C (dec.)

solubilidade

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

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

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)

chave InChI

KYRVNWMVYQXFEU-UHFFFAOYSA-N

Informações sobre genes

human ... TUBB(203068)

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Descrição geral

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.

Aplicação

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.

Ações bioquímicas/fisiológicas

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.

forma física

Color white to faint yellow and pink

Pictogramas

Health hazard
GHS08

Palavra indicadora

Warning

Frases de perigo

H341,H361d

Classificações de perigo

Muta. 2 - Repr. 2

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

Certificados de análise (COA)

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Colchicina ≥95% (HPLC), powder

Sigma-Aldrich

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Colchicina

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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