Thiocolchicine
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MedKoo CAT#: 406478

CAS#: 2730-71-4

Description: Thiocolchicine is a potent tubulin polymerization and microtubule assembly inhibitor, a axonal cytoskeleton modulator and apoptosis inducer. Structurally, thiocolchicine is a colchicine analog in which the C-10 methoxy is replaced with a thiomethyl moiety. Thiocolchicine was shown to bind with high affinity to the colchicine site on tubulin (Ka = 1.07 +/- 0.14 x 10(6) M-1). Thiocolchicine-dimers were shown to be potent topoisomerase I inhibitors.


Chemical Structure

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Thiocolchicine
CAS# 2730-71-4

Theoretical Analysis

MedKoo Cat#: 406478
Name: Thiocolchicine
CAS#: 2730-71-4
Chemical Formula: C22H25NO5S
Exact Mass: 415.14534
Molecular Weight: 415.5
Elemental Analysis: C, 63.59; H, 6.06; N, 3.37; O, 19.25; S, 7.72

Price and Availability

Size Price Availability Quantity
5.0mg USD 150.0 2 Weeks
10.0mg USD 250.0 2 Weeks
25.0mg USD 450.0 2 Weeks
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Synonym: Thiocolchicine.

IUPAC/Chemical Name: N-(1,2,3-trimethoxy-10-(methylthio)-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)acetamide

InChi Key: CMEGANPVAXDBPL-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H25NO5S/c1-12(24)23-16-8-6-13-10-18(26-2)21(27-3)22(28-4)20(13)14-7-9-19(29-5)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24)

SMILES Code: CC(NC1CCC2=CC(OC)=C(OC)C(OC)=C2C3=CC=C(SC)C(C=C13)=O)=O

Appearance: Solid powder

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

Preparing Stock Solutions

The following data is based on the product molecular weight 415.5 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.

Recalculate based on batch purity %
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

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1: Bartusik D, Tomanek B, Lattová E, Perreault H, Tuszynski J, Fallone G. Derivatives of thiocolchicine and its applications to CEM cells treatment using 19F magnetic resonance ex vivo. Bioorg Chem. 2010 Feb;38(1):1-6. doi: 10.1016/j.bioorg.2009.10.002. Epub 2009 Nov 1. PubMed PMID: 19944446.

2: Passarella D, Peretto B, Blasco y Yepes R, Cappelletti G, Cartelli D, Ronchi C, Snaith J, Fontana G, Danieli B, Borlak J. Synthesis and biological evaluation of novel thiocolchicine-podophyllotoxin conjugates. Eur J Med Chem. 2010 Jan;45(1):219-26. doi: 10.1016/j.ejmech.2009.09.047. Epub 2009 Oct 6. PubMed PMID: 19880222.

3: Passarella D, Giardini A, Peretto B, Fontana G, Sacchetti A, Silvani A, Ronchi C, Cappelletti G, Cartelli D, Borlak J, Danieli B. Inhibitors of tubulin polymerization: synthesis and biological evaluation of hybrids of vindoline, anhydrovinblastine and vinorelbine with thiocolchicine, podophyllotoxin and baccatin III. Bioorg Med Chem. 2008 Jun 1;16(11):6269-85. doi: 10.1016/j.bmc.2008.04.025. Epub 2008 May 28. PubMed PMID: 18468444.

4: Wang B, Pan XD, Liu HY, Yang J, Lü ZY, Zhao JH. Synthesis and antitumor activity of nitrogen-based thiocolchicine derivatives. Yao Xue Xue Bao. 2006 Nov;41(11):1057-63. PubMed PMID: 17262947.

5: Danieli B, Giardini A, Lesma G, Passarella D, Silvani A, Appendino G, Noncovich A, Fontana G, Bombardelli E, Sterner O. Synthesis and biological evaluation of paclitaxel-thiocolchicine hybrids. Chem Biodivers. 2004 Feb;1(2):327-45. PubMed PMID: 17191851.

6: Danieli B, Giardini A, Lesma G, Passarella D, Peretto B, Sacchetti A, Silvani A, Pratesi G, Zunino F. Thiocolchicine-podophyllotoxin conjugates: dynamic libraries based on disulfide exchange reaction. J Org Chem. 2006 Mar 31;71(7):2848-53. PubMed PMID: 16555841.

7: Lee SH, Park SK, Kim JM, Kim MH, Kim KH, Chun KW, Cho KH, Youn JY, Namgoong SK. New synthetic thiocolchicine derivatives as lowtoxic anticancer agents. Arch Pharm (Weinheim). 2005 Dec;338(12):582-9. PubMed PMID: 16353277.

8: Raspaglio G, Ferlini C, Mozzetti S, Prislei S, Gallo D, Das N, Scambia G. Thiocolchicine dimers: a novel class of topoisomerase-I inhibitors. Biochem Pharmacol. 2005 Jan 1;69(1):113-21. PubMed PMID: 15588720.

9: Ferri P, Bruno C, Cecchini T, Ciaroni S, Ambrogini P, Guidi L, Cuppini R, Bombardelli E, Morazzoni P, Riva A, Del Grande P. Effects of thiocolchicine on axonal cytoskeleton of the rat peroneus nerve. Exp Toxicol Pathol. 2002 Nov;54(3):211-6. PubMed PMID: 12484558.

10: Banerjee A, Kasmala LT, Hamel E, Sun L, Lee KH. Interaction of novel thiocolchicine analogs with the tubulin isoforms from bovine brain. Biochem Biophys Res Commun. 1999 Jan 19;254(2):334-7. PubMed PMID: 9918839.



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