Colchicine

Catalog #:

IN0048

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IN0048-1g

USD93.0

Synonyms: Colchicine

IUPAC Name:

N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide

Functional Activity:

Colchicine inhibits microtubule polymerization by binding to tubulin, one of the main constituents of microtubules. Availability of tubulin is essential to mitosis, and therefore colchicine effectively functions as a "mitotic poison" or spindle poison. Since one of the defining characteristics of cancer cells is a significantly increased rate of mitosis, this means that cancer cells are significantly more vulnerable to colchicine poisoning than are normal cells. However, the therapeutic value of colchicine against cancer is (as is typical with chemotherapy agents) limited by its toxicity against normal cells.

The mitosis inhibiting function of colchicine has been of great use in the study of cellular genetics. To see the chromosomes of a cell under a light microscope, it is important that they be viewed near the point in the cell cycle in which they are most dense. This occurs near the middle of mitosis, so mitosis must be stopped before it completes. Adding colchicine to a culture during mitosis is part of the standard procedure for doing karyotype studies.

Apart from inhibiting mitosis (a process heavily dependent on cytoskeletal changes), colchicine also inhibits neutrophil motility and activity, leading to a net anti-inflammatory effect.

Technical Data:

M.Wt: 399.44

Formula: C₂₂H₂₅ NO₆

Solubility: Soluble in 100 mM DMSO

Purity: >97%

Storage: Store at room temperature

CAS No.: 64-86-8

Special Conditions

This product is a Dangerous Good (UN2811) and carries a $10 dangerous goods packaging fee.

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References for Colchicine:

1. Huzil, J. T., Barakat, K., and Tuszynski, J. A. Electrostatic contributions to colchicine binding within tubulin isotypes. Electromagn Biol Med, 28: 355-364, 2009.

2. Tripathi, A., Durrant, D., Lee, R. M., Baruchello, R., Romagnoli, R., Simoni, D., and Kellogg, G. E. Hydropathic analysis and biological evaluation of stilbene derivatives as colchicine site microtubule inhibitors with anti-leukemic activity. J Enzyme Inhib Med Chem, 24: 1237-1244, 2009.

3. Fellows, M. D. and O'Donovan, M. R. Etoposide, cadmium chloride, benzo[a]pyrene, cyclophosphamide and colchicine tested in the in vitro mammalian cell micronucleus test (MNvit) in the presence and absence of cytokinesis block using L5178Y mouse lymphoma cells and 2-aminoanthracene tested in MNvit in the absence of cytokinesis block using TK6 cells at AstraZeneca UK, in support of OECD draft Test Guideline 487. Mutat Res, 702: 163-170.

4. Dahan, A., Sabit, H., and Amidon, G. L. Multiple efflux pumps are involved in the transepithelial transport of colchicine: combined effect of p-glycoprotein and multidrug resistance-associated protein 2 leads to decreased intestinal absorption throughout the entire small intestine. Drug Metab Dispos, 37: 2028-2036, 2009.

5. Soulere, L. Toward docking-based virtual screening for discovering antitubulin agents by targeting taxane and colchicine binding sites. ChemMedChem, 4: 161-163, 2009.

Certificate of Analysis/MSDS is available upon request with lot number