Synonym
Nocodazole; NSC 238159; NSC-238159; NSC238159; Oncodazole; R 17,934; R 17934; R-17934; R17934;
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
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
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].
Biological target:
Nocodazole (Oncodazole) is a rapidly-reversible inhibitor of microtubule.
In vitro activity:
A 48 hours exposure of human erythrocytes to nocodazole (≥ 30 µg/ml) significantly increased the percentage of annexin-V-binding cells without significantly modifying average forward scatter. Nocodazole significantly increased Fluo3-fluorescence, significantly increased DCF fluorescence and significantly increased ceramide surface abundance.
Reference: Cell Physiol Biochem. 2016;38(1):379-92. https://pubmed.ncbi.nlm.nih.gov/26824457/
In vivo activity:
For the in vivo tests, nocodazole -treated mice displayed elevated levels of IFN-γ, MCP-1 and IL-10 while Brucella-infected nocodazole -treated mice showed high levels of TNF, IFN-γ, MCP-1, IL-10 and IL-6 as compared to controls. Furthermore, nocodazole treatment reduced inflammation and Brucella proliferation in the spleens of mice.
Reference: Microb Pathog. 2017 Feb;103:87-93. https://pubmed.ncbi.nlm.nih.gov/28017899/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
3.0 |
9.96 |
| DMSO |
11.9 |
39.47 |
| DMSO:PBS (pH 7.2) (1:3) |
0.3 |
0.83 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
301.32
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Signoretto E, Honisch S, Briglia M, Faggio C, Castagna M, Lang F. Nocodazole Induced Suicidal Death of Human Erythrocytes. Cell Physiol Biochem. 2016;38(1):379-92. doi: 10.1159/000438638. Epub 2016 Jan 29. PMID: 26824457.
2. Ganguly A, Yang H, Sharma R, Patel KD, Cabral F. The role of microtubules and their dynamics in cell migration. J Biol Chem. 2012 Dec 21;287(52):43359-69. doi: 10.1074/jbc.M112.423905. Epub 2012 Nov 7. PMID: 23135278; PMCID: PMC3527923.
3. Reyes AW, Hop HT, Arayan LT, Huy TX, Min W, Lee HJ, Chang HH, Kim S. Nocodazole treatment interrupted Brucella abortus invasion in RAW 264.7 cells, and successfully attenuated splenic proliferation with enhanced inflammatory response in mice. Microb Pathog. 2017 Feb;103:87-93. doi: 10.1016/j.micpath.2016.11.028. Epub 2016 Dec 23. PMID: 28017899.
4. Attia SM, Ahmad SF, Okash RM, Bakheet SA. Dominant lethal effects of nocodazole in germ cells of male mice. Food Chem Toxicol. 2015 Mar;77:101-4. doi: 10.1016/j.fct.2015.01.004. Epub 2015 Jan 13. PMID: 25595372.
In vitro protocol:
1. Signoretto E, Honisch S, Briglia M, Faggio C, Castagna M, Lang F. Nocodazole Induced Suicidal Death of Human Erythrocytes. Cell Physiol Biochem. 2016;38(1):379-92. doi: 10.1159/000438638. Epub 2016 Jan 29. PMID: 26824457.
2. Ganguly A, Yang H, Sharma R, Patel KD, Cabral F. The role of microtubules and their dynamics in cell migration. J Biol Chem. 2012 Dec 21;287(52):43359-69. doi: 10.1074/jbc.M112.423905. Epub 2012 Nov 7. PMID: 23135278; PMCID: PMC3527923.
In vivo protocol:
1. Reyes AW, Hop HT, Arayan LT, Huy TX, Min W, Lee HJ, Chang HH, Kim S. Nocodazole treatment interrupted Brucella abortus invasion in RAW 264.7 cells, and successfully attenuated splenic proliferation with enhanced inflammatory response in mice. Microb Pathog. 2017 Feb;103:87-93. doi: 10.1016/j.micpath.2016.11.028. Epub 2016 Dec 23. PMID: 28017899.
2. Attia SM, Ahmad SF, Okash RM, Bakheet SA. Dominant lethal effects of nocodazole in germ cells of male mice. Food Chem Toxicol. 2015 Mar;77:101-4. doi: 10.1016/j.fct.2015.01.004. Epub 2015 Jan 13. PMID: 25595372.
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.
