Thiocolchicine

Names

[ Name ]:
Thiocolchicine

[Synonym ]:
thiocolhicine
N-[(7S)-1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide
10-Demethoxy-10-methylthiocolchicine
N-((S)-1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalen-7-yl)-acetamide
Thiocolchicine
thiocolchicine
EINECS 220-346-8
Colchicine,10-thio
N-((S)-1,2,3-Trimethoxy-10-methylmercapto-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalen-7-yl)-acetamid
Thiocholchicine
Colchicine,10-demethoxy-10-(methylthio)

Biological Activity

[Description]:

Thiocolchicine, a derivative modified in the C Ring of Colchicine (HY-16569) with enhanced biological properties. Thiocolchicine is a potent inhibitor of tubulin polymerization (IC50=2.5 µM) and competitively binds to tubulin with a Ki of 0.7 µM. Thiocolchicine induces cell apoptosis[1][2]. Thiocolchicine can be used as an ADC cytotoxin in ADC technology.

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin

Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin

[In Vitro]

Thiocolchicine is against MCF-7, LoVo, LoVo/DX, A-549 and BALB/3T3 cells with IC50 values of 0.01 μM, 0.021 μM, 0.398 μM, 0.011 μM and 0.114 μM, respectively[3]. Thiocolchicine (1 nM-100 μM; 24-72 hours) shows a relationship between cell cycle blocking activity and growth inhibition in breast cancer cells. It inhibits cell proliferation of MDA-MB-231 and multidrug resistant (MDR) MCF-7 ADRr breast cancer cells with IC50s of 0.6 nM and 400 nM, respectively, as well as MDR CEM-VBL leukemia cells (IC50=50 nM)[2].

[References]

[1]. Klaus M.Hahn, et al. Structural requirements for the binding of colchicine analogs to tubulin: the role of the C-10 substituent. Bioorganic & Medicinal Chemistry Letters.Volume 1, Issue 9, 1991, Pages 471-476

[2]. R De Vincenzo, et al. Antiproliferative Activity of Colchicine Analogues on MDR-positive and MDR-negative Human Cancer Cell Lines. Anticancer Drug Des. 1998 Jan;13(1):19-33.

Chemical & Physical Properties

[ Density]:
1.27g/cm3

[ Boiling Point ]:
729.1ºC at 760mmHg

[ Molecular Formula ]:
C₂₂H₂₅NO₅S

[ Molecular Weight ]:
415.50300

[ Flash Point ]:
394.7ºC

[ Exact Mass ]:
415.14500

[ PSA ]:
99.16000

[ LogP ]:
3.97580

[ Vapour Pressure ]:
4.12E-21mmHg at 25°C

[ Index of Refraction ]:
1.609

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GH0878800

CHEMICAL NAME :: Colchicine, 10-demethoxy-10-methylthio-

CAS REGISTRY NUMBER :: 2730-71-4

LAST UPDATED :: 199409

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C22-H25-N-O5-S

MOLECULAR WEIGHT :: 415.54

WISWESSER LINE NOTATION :: L B677 MV&T&J CO1 DO1 EO1 JMV1 NS1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 997 ug/kg

TOXIC EFFECTS :: Tumorigenic - active as anti-cancer agent

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 24,636,1981

Safety Information

[ Symbol ]:

GHS05, GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300 + H330-H318-H340

[ Precautionary Statements ]:
P201-P260-P264-P280-P284-P301 + P310

[ Hazard Codes ]:
T+

[ RIDADR ]:
UN 1544PSN1 6.1 / PGI

Precursor & DownStream

Precursor

DownStream

Articles

Antiproliferative activity of colchicine analogues on MDR-positive and MDR-negative human cancer cell lines.

Anticancer Drug Des. 13 , 19-33, (1998)

In this study the in vitro antitumor activity of a series of 20 colchicine analogues was tested and compared with colchicine and thiocolchicine on three different human cancer cell lines, two of which...

Antitumor agents--CLXXV. Anti-tubulin action of (+)-thiocolchicine prepared by partial synthesis.

Bioorg. Med. Chem. 5(12) , 2277-82, (1997)

(+)-Thiocolchicine (2b) was prepared from (+/-)-colchicine (1) in a five-step reaction sequence that included chromatographic separation of appropriate camphanylated diastereomers. Acid hydrolysis of ...

Thiocolchicine dimers: a novel class of topoisomerase-I inhibitors.

Biochem. Pharmacol. 69(1) , 113-21, (2005)

During a cellular screening of thiocolchicine analogs, thiocolchicine dimers resulted particularly active in cisplatin-resistant A2780-CIS cells. In order to discover by which mechanism(s) thiocolchic...

Related Compounds

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