Date published: 2025-12-6

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Thiocolchicine (CAS 2730-71-4)

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Alternate Names:
10-Thio-colchicine
Application:
Thiocolchicine is a specific tubulin synthesis inhibitor and Topo I inhibitor
CAS Number:
2730-71-4
Molecular Weight:
415.5
Molecular Formula:
C22H25NO5S
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Thiocolchicine, a derivative of colchicine, exhibits potent inhibition of microtubule assembly (IC50 = 2.5 µM). By impeding the binding of colchicine to tubulin (Ki = 0.7 µM in a radioligand binding assay), it exerts its inhibitory effects. Thiocolchicine proves effective in suppressing the proliferation of MDA-MB-231. Functioning as an antimitotic alkaloid, thiocolchicine plays a role as an inhibitor of tubulin polymerization and microtubule assembly, thereby modulating the axonal cytoskeleton. It also serves as an apoptosis inducer. Notably, the presence of thiocolchicine-dimers demonstrates potent inhibition of topoisomerase I activity. Structurally analogous to colchicine, thiocolchicine replaces the C-10 methoxy group with a thiomethyl moiety. This substitution enables high-affinity binding to the colchicine site on tubulin (Ka = 1.07 +/- 0.14 x 10 M-1). Additionally, the formation of thiocolchicine-dimers further enhances its potency as a topoisomerase I inhibitor.


Thiocolchicine (CAS 2730-71-4) References

  1. Effects of thiocolchicine on axonal cytoskeleton of the rat peroneus nerve.  |  Ferri, P., et al. 2002. Exp Toxicol Pathol. 54: 211-6. PMID: 12484558
  2. [Antimitotic activity and toxicity of some derivatives of colchicine and thiocolchicine].  |  JEQUIER, R., et al. 1955. Arch Int Pharmacodyn Ther. 103: 243-55. PMID: 13259737
  3. Colchicine analogues: effect on amyloidogenesis in a murine model and, in vitro, on polymorphonuclear leukocytes.  |  Wolach, B., et al. 1992. Eur J Clin Invest. 22: 630-4. PMID: 1459179
  4. Synthesis and biological evaluation of paclitaxel-thiocolchicine hybrids.  |  Danieli, B., et al. 2004. Chem Biodivers. 1: 327-45. PMID: 17191851
  5. Synthesis and antitumor activity of nitrogen-based thiocolchicine derivatives.  |  Wang, B., et al. 2006. Yao Xue Xue Bao. 41: 1057-63. PMID: 17262947
  6. Inhibitors of tubulin polymerization: synthesis and biological evaluation of hybrids of vindoline, anhydrovinblastine and vinorelbine with thiocolchicine, podophyllotoxin and baccatin III.  |  Passarella, D., et al. 2008. Bioorg Med Chem. 16: 6269-85. PMID: 18468444
  7. Synthesis and biological evaluation of novel thiocolchicine-podophyllotoxin conjugates.  |  Passarella, D., et al. 2010. Eur J Med Chem. 45: 219-26. PMID: 19880222
  8. Conformation of thiocolchicine and two B-ring-modified analogues bound to tubulin studied with optical spectroscopy.  |  Lincoln, P., et al. 1991. Biochemistry. 30: 1179-87. PMID: 1991097
  9. N-acetylcolchinol O-methyl ether and thiocolchicine, potent analogs of colchicine modified in the C ring. Evaluation of the mechanistic basis for their enhanced biological properties.  |  Kang, GJ., et al. 1990. J Biol Chem. 265: 10255-9. PMID: 2191947
  10. Antitubulin effects of derivatives of 3-demethylthiocolchicine, methylthio ethers of natural colchicinoids, and thioketones derived from thiocolchicine. Comparison with colchicinoids.  |  Muzaffar, A., et al. 1990. J Med Chem. 33: 567-71. PMID: 2299625
  11. Experimental and computational study of the interaction of novel colchicinoids with a recombinant human αI/βI-tubulin heterodimer.  |  Mane, JY., et al. 2013. Chem Biol Drug Des. 82: 60-70. PMID: 23480279
  12. Association of thiocolchicine with tubulin.  |  Chabin, RM. and Hastie, SB. 1989. Biochem Biophys Res Commun. 161: 544-50. PMID: 2735908
  13. Synthesis and Antiproliferative Screening Of Novel Analogs of Regioselectively Demethylated Colchicine and Thiocolchicine.  |  Czerwonka, D., et al. 2020. Molecules. 25: PMID: 32151042
  14. New Class of Betulinic Acid-Based Nanoassemblies of Cabazitaxel, Podophyllotoxin, and Thiocolchicine.  |  Colombo, E., et al. 2020. ACS Med Chem Lett. 11: 895-898. PMID: 32435402
  15. A novel synthesis of colchicide and analogues from thiocolchicine and congeners: reevaluation of colchicide as a potential antitumor agent.  |  Dumont, R., et al. 1987. J Med Chem. 30: 732-5. PMID: 3560165

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Thiocolchicine, 5 mg

sc-202838A
5 mg
$125.00

Thiocolchicine, 100 mg

sc-202838
100 mg
$194.00