M1404

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

Properties

• 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)

Description

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

Safety Information

• pictograms: GHS08
• signalword: Warning
• hcodes: H341,H361d
• pcodes: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Muta. 2 - Repr. 2
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)