For research use only. Not for therapeutic Use.
Thiocolchicine（Cat No.:R048124）is a natural alkaloid derived from the plant Colchicum autumnale, primarily known for its anti-inflammatory and analgesic properties. Structurally related to colchicine, it exhibits potential in treating conditions like gout and other inflammatory disorders by disrupting microtubule polymerization, which affects cellular processes such as mitosis and inflammation. Thiocolchicine has also shown promise in cancer research due to its ability to inhibit cell proliferation. Ongoing studies are investigating its mechanisms of action and potential therapeutic applications, positioning thiocolchicine as a compound of interest in both medicinal and pharmacological fields.
| Catalog Number | R048124 |
| CAS Number | 2730-71-4 |
| Synonyms | N-[(7S)-5,6,7,9-Tetrahydro-1,2,3-trimethoxy-10-(methylthio)-9-oxobenzo[a]heptalen-7-yl]acetamide; 10-Thio-colchicine; 10-Demethoxy-10-(methylthio)colchicine; NSC 186301; |
| Molecular Formula | C22H25NO5S |
| 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)N[C@H]1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)SC)OC)OC)OC |
| Reference | </br>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 Article</br>2: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 </br>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 </br>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 </br>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 </br>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 </br>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 </br>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 </br>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 </br>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 |
