MedKoo Cat#: 406478 | Name: Thiocolchicine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Thiocolchicine
Thiocolchicine
CAS#2730-71-4

Theoretical Analysis

MedKoo Cat#: 406478

Name: Thiocolchicine

CAS#: 2730-71-4

Chemical Formula: C22H25NO5S

Exact Mass: 415.1453

Molecular Weight: 415.50

Elemental Analysis: C, 63.59; H, 6.06; N, 3.37; O, 19.25; S, 7.72

Price and Availability

Size Price Availability Quantity
5mg USD 150.00
10mg USD 250.00
25mg USD 450.00
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Related CAS #
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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
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Preparing Stock Solutions

The following data is based on the product molecular weight 415.50 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
1: Colombo E, Coppini DA, Polito L, Ciriello U, Paladino G, Hyeraci M, Di Paolo ML, Nordio G, Dalla Via L, Passarella D. Cannabidiol as Self-Assembly Inducer for Anticancer Drug-Based Nanoparticles. Molecules. 2022 Dec 23;28(1):112. doi: 10.3390/molecules28010112. PMID: 36615306; PMCID: PMC9822096. 2: Czerwonka D, Maj E, Wietrzyk J, Huczyński A. Synthesis of thiocolchicine amine derivatives and evaluation of their antiproliferative activity. Bioorg Med Chem Lett. 2021 Nov 15;52:128382. doi: 10.1016/j.bmcl.2021.128382. Epub 2021 Sep 27. PMID: 34592435. 3: Klejborowska G, Urbaniak A, Maj E, Wietrzyk J, Moshari M, Preto J, Tuszynski JA, Chambers TC, Huczyński A. Synthesis, anticancer activity and molecular docking studies of N-deacetylthiocolchicine and 4-iodo-N-deacetylthiocolchicine derivatives. Bioorg Med Chem. 2021 Feb 15;32:116014. doi: 10.1016/j.bmc.2021.116014. Epub 2021 Jan 11. PMID: 33465696. 4: Colombo E, Polito L, Biocotino M, Marzullo P, Hyeraci M, Via LD, Passarella D. New Class of Betulinic Acid-Based Nanoassemblies of Cabazitaxel, Podophyllotoxin, and Thiocolchicine. ACS Med Chem Lett. 2020 Feb 28;11(5):895-898. doi: 10.1021/acsmedchemlett.9b00668. PMID: 32435402; PMCID: PMC7236225. 5: Pallante L, Rocca A, Klejborowska G, Huczynski A, Grasso G, Tuszynski JA, Deriu MA. In silico Investigations of the Mode of Action of Novel Colchicine Derivatives Targeting β-Tubulin Isotypes: A Search for a Selective and Specific β-III Tubulin Ligand. Front Chem. 2020 Feb 21;8:108. doi: 10.3389/fchem.2020.00108. PMID: 32154219; PMCID: PMC7047339. 6: Czerwonka D, Sobczak S, Maj E, Wietrzyk J, Katrusiak A, Huczyński A. Synthesis and Antiproliferative Screening Of Novel Analogs of Regioselectively Demethylated Colchicine and Thiocolchicine. Molecules. 2020 Mar 5;25(5):1180. doi: 10.3390/molecules25051180. PMID: 32151042; PMCID: PMC7179419. 7: Urbaniak A, Jousheghany F, Piña-Oviedo S, Yuan Y, Majcher-Uchańska U, Klejborowska G, Moorjani A, Monzavi-Karbassi B, Huczyński A, Chambers TC. Carbamate derivatives of colchicine show potent activity towards primary acute lymphoblastic leukemia and primary breast cancer cells-in vitro and ex vivo study. J Biochem Mol Toxicol. 2020 Jun;34(6):e22487. doi: 10.1002/jbt.22487. Epub 2020 Mar 5. PMID: 32141170. 8: Klejborowska G, Urbaniak A, Maj E, Preto J, Moshari M, Wietrzyk J, Tuszynski JA, Chambers TC, Huczyński A. Synthesis, biological evaluation and molecular docking studies of new amides of 4-chlorothiocolchicine as anticancer agents. Bioorg Chem. 2020 Apr;97:103664. doi: 10.1016/j.bioorg.2020.103664. Epub 2020 Feb 13. PMID: 32106039. 9: Bonandi E, Foschi F, Marucci C, Dapiaggi F, Sironi M, Pieraccini S, Christodoulou MS, de Asís Balaguer F, Díaz JF, Zidar N, Passarella D. Synthesis of Thicolchicine-Based Conjugates: Investigation towards Bivalent Tubulin/Microtubules Binders. Chempluschem. 2019 Jan;84(1):98-102. doi: 10.1002/cplu.201800497. PMID: 31950734. 10: Klejborowska G, Urbaniak A, Preto J, Maj E, Moshari M, Wietrzyk J, Tuszynski JA, Chambers TC, Huczyński A. Synthesis, biological evaluation and molecular docking studies of new amides of 4-bromothiocolchicine as anticancer agents. Bioorg Med Chem. 2019 Dec 1;27(23):115144. doi: 10.1016/j.bmc.2019.115144. Epub 2019 Oct 8. PMID: 31653441. 11: Klejborowska G, Moshari M, Maj E, Majcher U, Preto J, Wietrzyk J, Tuszynski JA, Huczyński A. Synthesis, antiproliferative activity, and molecular docking studies of 4-chlorothiocolchicine analogues. Chem Biol Drug Des. 2020 Jan;95(1):182-191. doi: 10.1111/cbdd.13618. Epub 2019 Sep 20. PMID: 31483093. 12: Fumagalli G, Polito L, Colombo E, Foschi F, Christodoulou MS, Galeotti F, Perdicchia D, Bassanini I, Riva S, Seneci P, García-Argáez A, Dalla Via L, Passarella D. Self-assembling Releasable Thiocolchicine-Diphenylbutenylaniline Conjugates. ACS Med Chem Lett. 2019 Jan 4;10(4):611-614. doi: 10.1021/acsmedchemlett.8b00605. PMID: 30996805; PMCID: PMC6466830. 13: Majcher U, Klejborowska G, Kaik M, Maj E, Wietrzyk J, Moshari M, Preto J, Tuszynski JA, Huczyński A. Synthesis and Biological Evaluation of Novel Triple- Modified Colchicine Derivatives as Potent Tubulin-Targeting Anticancer Agents. Cells. 2018 Nov 19;7(11):216. doi: 10.3390/cells7110216. PMID: 30463236; PMCID: PMC6262455. 14: Majcher U, Klejborowska G, Moshari M, Maj E, Wietrzyk J, Bartl F, Tuszynski JA, Huczyński A. Antiproliferative Activity and Molecular Docking of Novel Double-Modified Colchicine Derivatives. Cells. 2018 Nov 1;7(11):192. doi: 10.3390/cells7110192. PMID: 30388878; PMCID: PMC6262536. 15: Majcher U, Urbaniak A, Maj E, Moshari M, Delgado M, Wietrzyk J, Bartl F, Chambers TC, Tuszynski JA, Huczyński A. Synthesis, antiproliferative activity and molecular docking of thiocolchicine urethanes. Bioorg Chem. 2018 Dec;81:553-566. doi: 10.1016/j.bioorg.2018.09.004. Epub 2018 Sep 12. PMID: 30248507. 16: Russo GI, Milenkovic U, Hellstrom W, Levine LA, Ralph D, Albersen M. Clinical Efficacy of Injection and Mechanical Therapy for Peyronie's Disease: A Systematic Review of the Literature. Eur Urol. 2018 Dec;74(6):767-781. doi: 10.1016/j.eururo.2018.07.005. Epub 2018 Sep 17. PMID: 30237020. 17: Toscano L Jr, Rezende MV, Mello LF, Paulillo D, Glina S. A prospective, randomized, single - blind study comparing intraplaque injection of thiocolchicine and verapamil in Peyronie's Disease: a pilot study. Int Braz J Urol. 2016 Sep-Oct;42(5):1005-1009. doi: 10.1590/S1677-5538.IBJU.2015.0598. PMID: 24893912; PMCID: PMC5066899. 18: Marangon J, Christodoulou MS, Casagrande FV, Tiana G, Dalla Via L, Aliverti A, Passarella D, Cappelletti G, Ricagno S. Tools for the rational design of bivalent microtubule-targeting drugs. Biochem Biophys Res Commun. 2016 Oct 7;479(1):48-53. doi: 10.1016/j.bbrc.2016.09.022. Epub 2016 Sep 7. PMID: 27613098. 19: Ho CT, Chang YJ, Yang LX, Wei PL, Liu TZ, Liu JJ. A Novel Microtubule- Disrupting Agent Induces Endoplasmic Reticular Stress-Mediated Cell Death in Human Hepatocellular Carcinoma Cells. PLoS One. 2015 Sep 10;10(9):e0136340. doi: 10.1371/journal.pone.0136340. PMID: 26355599; PMCID: PMC4565632. 20: Ponzone C, Berlanda D, Donzelli F, Acquati V, Ciulla R, Negrini A, Rovati M, Evangelista D, Fata E, Ciceri D, Perterlongo F, Cabri W. Biotransformation of colchicinoids into their corresponding 3-O-glucosyl derivatives by selected strains of Bacillus megaterium. Mol Biotechnol. 2014 Jul;56(7):653-9. doi: 10.1007/s12033-014-9741-5. PMID: 24553816.