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Nocodazole information


Nocodazole
Names
IUPAC name
Methyl [5-(2-thienylcarbonyl)-1H-benzimidazol-2-yl]carbamate
Identifiers
CAS Number
  • 31430-18-9 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:34892 ☒N
ChEMBL
  • ChEMBL9514 ☒N
ChemSpider
  • 3979 ☒N
ECHA InfoCard 100.046.008 Edit this at Wikidata
EC Number
  • 250-626-5
KEGG
  • C13719 ☒N
PubChem CID
  • 4122
UNII
  • SH1WY3R615 ☒N
CompTox Dashboard (EPA)
  • DTXSID9031800 Edit this at Wikidata
InChI
  • 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) ☒N
    Key: KYRVNWMVYQXFEU-UHFFFAOYSA-N ☒N
  • InChI=1/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)
    Key: KYRVNWMVYQXFEU-UHFFFAOYAF
SMILES
  • O=C(C2=CC=CS2)C1=CC=C(N=C(NC(OC)=O)N3)C3=C1
Properties
Chemical formula
C14H11N3O3S
Molar mass 301.32 g·mol−1
Appearance White with faint yellow cast powder
Melting point 256 °C (493 °F; 529 K)
Solubility in water
Approximately 10 mg/mL in DMSO
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Nocodazole is an antineoplastic agent which exerts its effect in cells by interfering with the polymerization of microtubules.[1] Microtubules are one type of fibre which constitutes the cytoskeleton, and the dynamic microtubule network has several important roles in the cell, including vesicular transport, forming the mitotic spindle and in cytokinesis. Several drugs including vincristine and colcemid are similar to nocodazole in that they interfere with microtubule polymerization.

Nocodazole has been shown to decrease the oncogenic potential of cancer cells via another microtubules-independent mechanisms. Nocodazole stimulates the expression of LATS2 which potently inhibits the Wnt signaling pathway by abrogating the interaction between the Wnt-dependent transcriptional co-factors beta-catenin and BCL9.[2]

It is related to mebendazole by replacement of the left most benzene ring by thiophene.

  1. ^ Kuhn, Michael (17 January 2006). "The microtubule depolymerizing drugs nocodazole and colchicine inhibit the uptake of Listeria monocytogenes by P388D1 macrophages". FEMS Microbiology Letters. 160 (1): 87–90. doi:10.1111/j.1574-6968.1998.tb12895.x. PMID 9495017.
  2. ^ Li, Jiong; Chen, Xiaohong; Ding, Xiangming; Cheng, Yingduan; Zhao, Bin; Lai, Zhi-Chun; Al Hezaimi, Khalid; Hakem, Razqallah; Guan, Kun-Liang (2013-12-26). "LATS2 suppresses oncogenic Wnt signaling by disrupting β-catenin/BCL9 interaction". Cell Reports. 5 (6): 1650–1663. doi:10.1016/j.celrep.2013.11.037. ISSN 2211-1247. PMC 3897473. PMID 24360964.

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Nocodazole

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Fenbendazole

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active metabolite of another anthelmintic drug, febantel. Ivermectin Nocodazole Praziquantel "Fenbendazole: From MD Anderson to Joe Tippens". Institute...

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Cell synchronization

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dividing cells. Cells will remain arrested until the nocodazole has been washed out. Nocodazole does not appear to disrupt interphase metabolism, and...

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Induced cell cycle arrest

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cell cycle again. Nocodazole is a chemical agent that interferes with the polymerization of microtubules. Cells treated with nocodazole arrest with a G2...

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Synchronous culture

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removed from the culture and the cells then begin to grow synchronously. Nocodazole, for example, has been used in biological research for synchronization...

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Vinblastine

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cycles. Microtubule-disruptive drugs like vinblastine, colcemid, and nocodazole have been reported to act by two mechanisms. At very low concentrations...

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Praziquantel

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cause problems in dogs with MDR1 mutations. Fenbendazole Oxfendazole Nocodazole "Product monograph brand safety updates". Health Canada. February 2024...

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Cytoskeletal drugs

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Wadsworth P, Cassimeris L (June 1997). "Nanomolar concentrations of nocodazole alter microtubule dynamic instability in vivo and in vitro". Molecular...

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Microtubule

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e.g. Ixabepilone, work in a similar way to the taxanes. Vinorelbine, Nocodazole, vincristine, and colchicine have the opposite effect, blocking the polymerization...

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Mad2

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metaphase-to-anaphase transition in response to the microtubule poison nocodazole. Subsequent cloning of the Xenopus laevis orthologue, facilitated by the...

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Nuclear transfer

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used to increase cloning efficiency. Microtubule inhibitors, such as nocodazole, are used to arrest the oocyte in M phase, during which its nuclear membrane...

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Spindle checkpoint

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mechanism exists at the metaphase-to-anaphase transition. Using drugs such as nocodazole and colchicine, the mitotic spindle disassembles and the cell cycle is...

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Epiboly

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progresses. Treating embryos with the microtubule depolymerizing agent nocodazole completely blocks epiboly of the YSL and partially blocks epiboly of the...

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Asymmetric cell division

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the prospective smaller AB cell become downregulated. Experiments using nocodazole and taxol support this observation. Taxol, which stabilized microtubules...

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Purinosome

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polymerization with nocodazole blocks formation of the purinosome macrobodies, and reduces the flux of de novo purine biosynthesis. However, nocodazole also blocks...

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Stress granule

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is based on the fact that disruption of microtubules with the chemical nocodazole blocks the appearance of the granules. Furthermore, many signaling molecules...

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Anterograde tracing

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of substances interacting with microtubular function and axonal flow [nocodazole, taxol and erythro-9-3-(2-hydroxynonyl)adenine]". The Journal of General...

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DRG2

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"Overexpression of DRG2 increases G2/M phase cells and decreases sensitivity to nocodazole-induced apoptosis". J. Biochem. 135 (3): 331–5. doi:10.1093/jb/mvh040...

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Telomeres in the cell cycle

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found that when the cells were released and concurrently treated with nocodazole, a G2/M phase cell cycle inhibitor, telomere length increased for the...

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MAP6

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calmodulin binding domain and stabilize microtubules against both cold and nocodazole-induced depolymerization by forming bridges with adjacent tubulin heterodimers...

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HSPA1B

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response to arachidonic acid and the microtubule-depolymerizing drug nocodazole". The Biochemical Journal. 385 (Pt 1): 45–56. doi:10.1042/BJ20040690....

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Aurora kinase C

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when overexpressed. When cells overexpressing Aurora C were treated with nocodazole to turn on the SAC, Aurora B protein stability and activity decreased...

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Control of chromosome duplication

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CDKs regulate the localization of Mcm2-7 is that inactivation of CDKs in nocodazole arrested cells induced accumulation of Mcm2-7 in the nucleus. Cdt1 is...

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