Thiocolchicine

• CAT Number: R048124
• CAS Number: 2730-71-4
• Molecular Formula: C22H25NO5S
• Molecular Weight: 415.504
• Purity: ≥95%
• Target: microtublin inhibitor
• Storage: -20°C
• IUPAC Name: N-[(7S)-1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
• InChI: 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)/t16-/m0/s1
• InChIKey: CMEGANPVAXDBPL-INIZCTEOSA-N
• SMILES: CC(=O)NC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)SC)OC)OC)OC

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.

Reference

1:A prospective, randomized, single – blind study comparing intraplaque injection of thiocolchicine and verapamil in Peyronie/’s Disease: a pilot study. Toscano L Jr, Rezende MV, Mello LF, Paulillo D, Glina S.Int Braz J Urol. 2016 Sep-Oct;42(5):1005-1009. doi: 10.1590/S1677-5538.IBJU.2015.0598. PMID: 24893912 Free PMC Article2:Derivatives of thiocolchicine and its applications to CEM cells treatment using 19F magnetic resonance ex vivo. Bartusik D, Tomanek B, Lattová E, Perreault H, Tuszynski J, Fallone G.Bioorg Chem. 2010 Feb;38(1):1-6. doi: 10.1016/j.bioorg.2009.10.002. Epub 2009 Nov 1. PMID: 19944446 3:Synthesis and biological evaluation of novel thiocolchicine-podophyllotoxin conjugates. Passarella D, Peretto B, Blasco y Yepes R, Cappelletti G, Cartelli D, Ronchi C, Snaith J, Fontana G, Danieli B, Borlak J.Eur J Med Chem. 2010 Jan;45(1):219-26. doi: 10.1016/j.ejmech.2009.09.047. Epub 2009 Oct 6. PMID: 19880222 4:Inhibitors of tubulin polymerization: synthesis and biological evaluation of hybrids of vindoline, anhydrovinblastine and vinorelbine with thiocolchicine, podophyllotoxin and baccatin III. Passarella D, Giardini A, Peretto B, Fontana G, Sacchetti A, Silvani A, Ronchi C, Cappelletti G, Cartelli D, Borlak J, Danieli B.Bioorg Med Chem. 2008 Jun 1;16(11):6269-85. doi: 10.1016/j.bmc.2008.04.025. Epub 2008 May 28. PMID: 18468444 5:Synthesis and antitumor activity of nitrogen-based thiocolchicine derivatives. Wang B, Pan XD, Liu HY, Yang J, Lü ZY, Zhao JH.Yao Xue Xue Bao. 2006 Nov;41(11):1057-63. PMID: 17262947 6:Synthesis and biological evaluation of paclitaxel-thiocolchicine hybrids. Danieli B, Giardini A, Lesma G, Passarella D, Silvani A, Appendino G, Noncovich A, Fontana G, Bombardelli E, Sterner O.Chem Biodivers. 2004 Feb;1(2):327-45. PMID: 17191851 7:Thiocolchicine-podophyllotoxin conjugates: dynamic libraries based on disulfide exchange reaction. Danieli B, Giardini A, Lesma G, Passarella D, Peretto B, Sacchetti A, Silvani A, Pratesi G, Zunino F.J Org Chem. 2006 Mar 31;71(7):2848-53. PMID: 16555841 8:New synthetic thiocolchicine derivatives as lowtoxic anticancer agents. Lee SH, Park SK, Kim JM, Kim MH, Kim KH, Chun KW, Cho KH, Youn JY, Namgoong SK.Arch Pharm (Weinheim). 2005 Dec;338(12):582-9. PMID: 16353277 9:Thiocolchicine dimers: a novel class of topoisomerase-I inhibitors. Raspaglio G, Ferlini C, Mozzetti S, Prislei S, Gallo D, Das N, Scambia G.Biochem Pharmacol. 2005 Jan 1;69(1):113-21. PMID: 15588720 10:Effects of thiocolchicine on axonal cytoskeleton of the rat peroneus nerve. Ferri P, Bruno C, Cecchini T, Ciaroni S, Ambrogini P, Guidi L, Cuppini R, Bombardelli E, Morazzoni P, Riva A, Del Grande P.Exp Toxicol Pathol. 2002 Nov;54(3):211-6. PMID: 12484558