Synonym:

IUPAC/Chemical Name: methyl (5-(thiophene-2-carbonyl)-1H-benzo[d]imidazol-2-yl)carbamate

InChi Key: KYRVNWMVYQXFEU-UHFFFAOYSA-N

InChi Code: 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 Code: O=C(OC)NC1=NC2=CC(C(C3=CC=CS3)=O)=CC=C2N1

Technical Data

Additional Information

Nocodazole is an anti-neoplastic agent which exerts its effect in cells by interfering with the polymerization of microtubules. 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 polymerisation. As nocodazole affects the cytoskeleton, it is often used in cell biology experiments as a control: for example, some dominant negative Rho small GTPases cause a similar effect as nocodazole, and constitutively activated mutants often reverse or negate the effect. Nocodazole is frequently used in cell biology laboratories to synchronize the cell division cycle. Cells treated with nocodazole arrest with a G2- or M-phase DNA content when analysed by flow cytometry. Microscopy of nocodazole-treated cells shows that they do enter mitosis but cannot form metaphase spindles because microtubules (of which the spindles are made) cannot polymerise. The absence of microtubule attachment to kinetochores activates the spindle assembly checkpoint, causing the cell to arrest in prometaphase. For cell synchronization experiments, nocodazole is usually used at a concentration of 40-100 ng/mL of culture medium for a duration of 12-18 hrs. Prolonged arrest of cells in mitosis due to nocodazole treatment typically results in cell death by apoptosis. Another standard cell biological application of nocodazole is to induce the formation of Golgi ministacks in eukaryotic cells. The perinuclear structural organization of the Golgi apparatus in eukaryotes is dependent on microtubule trafficking, but disrupting the trafficking of Golgi elements from the endoplasmic reticulum treatment with nocodazole (33 uM for 3 hours works) induces numerous Golgi elements to form adjacent to ER exit sites. These functional Golgi ministacks remain distributed about the cell, unable to track forward to form a perinuclear Golgi since nocodazole has depolymerized the microtubules.  [source: http://en.wikipedia.org/wiki/Nocodazole].  
 [source: http://en.wikipedia.org/wiki/Nocodazole].  

References

 1: Costa-Borges N, Paramio MT, Santaló J, Ibáñez E. Demecolcine- and nocodazole-induced enucleation in mouse and goat oocytes for the preparation of recipient cytoplasts in somatic cell nuclear transfer procedures. Theriogenology. 2010 Nov 11. [Epub ahead of print] PubMed PMID: 21074837.

2: Samuel T, Fadlalla K, Turner T, Yehualaeshet TE. The flavonoid quercetin transiently inhibits the activity of taxol and nocodazole through interference with the cell cycle. Nutr Cancer. 2010 Nov;62(8):1025-35. PubMed PMID: 21058190.

3: Endo K, Mizuguchi M, Harata A, Itoh G, Tanaka K. Nocodazole induces mitotic cell death with apoptotic-like features in Saccharomyces cerevisiae. FEBS Lett. 2010 Jun 3;584(11):2387-92. Epub 2010 Apr 20. PubMed PMID: 20399776.

4: Lee J, You J, Kim J, Hyun SH, Lee E. Postactivation treatment with nocodazole maintains normal nuclear ploidy of cloned pig embryos by increasing nuclear retention and formation of single pronucleus. Theriogenology. 2010 Mar 1;73(4):429-36. Epub 2009 Dec 8. PubMed PMID: 20004011.

5: Hunsperger EA, Roehrig JT. Nocodazole delays viral entry into the brain following footpad inoculation with West Nile virus in mice. J Neurovirol. 2009;15(3):211-8. PubMed PMID: 19444694.

6: Fuchs YF, Eisler SA, Link G, Schlicker O, Bunt G, Pfizenmaier K, Hausser A. A Golgi PKD activity reporter reveals a crucial role of PKD in nocodazole-induced Golgi dispersal. Traffic. 2009 Jul;10(7):858-67. Epub 2009 Apr 25. PubMed PMID: 19416469.

7: Nagano K, Shinkawa T, Mutoh H, Kondoh O, Morimoto S, Inomata N, Ashihara M, Ishii N, Aoki Y, Haramura M. Phosphoproteomic analysis of distinct tumor cell lines in response to nocodazole treatment. Proteomics. 2009 May;9(10):2861-74. PubMed PMID: 19415658.

8: Li D, Li P, Li G, Wang J, Wang E. The effect of nocodazole on the transfection efficiency of lipid-bilayer coated gold nanoparticles. Biomaterials. 2009 Mar;30(7):1382-8. Epub 2008 Dec 17. PubMed PMID: 19091395.

9: Poxleitner MK, Dawson SC, Cande WZ. Cell cycle synchrony in Giardia intestinalis cultures achieved by using nocodazole and aphidicolin. Eukaryot Cell. 2008 Apr;7(4):569-74. Epub 2008 Feb 22. PubMed PMID: 18296622; PubMed Central PMCID: PMC2292626.

10: Chang YC, Nalbant P, Birkenfeld J, Chang ZF, Bokoch GM. GEF-H1 couples nocodazole-induced microtubule disassembly to cell contractility via RhoA. Mol Biol Cell. 2008 May;19(5):2147-53. Epub 2008 Feb 20. PubMed PMID: 18287519; PubMed Central PMCID: PMC2366883.