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Key Documents

SML0954

Sigma-Aldrich

Thiocolchicine

≥97% (HPLC)

Synonym(s):

10-Demethoxy-10-(methylthio)colchicine, 10-Thio-colchicine, N-[(7S)-5,6,7,9-Tetrahydro-1,2,3-trimethoxy-10-(methylthio)-9-oxobenzo[a]heptalen-7-yl]-acetamide, NSC 186301

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About This Item

Empirical Formula (Hill Notation):
C22H25NO5S
CAS Number:
2730-71-4
Molecular Weight:
415.50
EC Number:
220-346-8
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

−20°C

SMILES string

S(C)c1[c](cc2c(cc1)c3c(cc(c(c3OC)OC)OC)CC[C@@H]2NC(=O)C)=O

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

InChI key

CMEGANPVAXDBPL-INIZCTEOSA-N

Biochem/physiol Actions

Thiocolchicine is an antimitotic alkaloid and apoptosis inducer that inhibits tubulin polymerization and microtubule assembly.
Thiocolchicine is an antimitotic alkaloid and apoptosis inducer.

Signal Word

Danger

Hazard Statements

H300 + H330,H318,H340

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Oral - Eye Dam. 1 - Muta. 1B

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000074359
0000074360
0000018668
024M4745V

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Bruno Danieli et al.
Chemistry & biodiversity, 1(2), 327-345 (2006-12-29)
The bifunctional taxoid-colchicinoid hybrids 6-8 were synthesized and evaluated in assays of cytotoxicity and tubulin assembly/disassembly. All compounds showed a high degree of cytotoxicity, but, while 6 and 7 behaved as bifunctional tubulin binders not unlike an equimolecular mixture of
Q Shi et al.
Bioorganic & medicinal chemistry, 5(12), 2277-2282 (1998-02-12)
(+)-Thiocolchicine (2b) was prepared from (+/-)-colchicine (1) in a five-step reaction sequence that included chromatographic separation of appropriate camphanylated diastereomers. Acid hydrolysis of the (+)-diastereomer, followed by acetylation, yielded the desired product 2b. (+)-Thiocolchicine has 15-fold lower inhibitory activity against
Giuseppina Raspaglio et al.
Biochemical pharmacology, 69(1), 113-121 (2004-12-14)
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) thiocolchicine dimers overcame cisplatin resistance, p53, p21waf1 and MLH1 were assessed by Western blot. Results pointed out
B Wolach et al.
European journal of clinical investigation, 22(9), 630-634 (1992-09-01)
Colchicine has been used in diverse clinical settings such as gout, familial Mediterranean fever, liver cirrhosis, Behcet's disease and pericarditis. It also has an antimitotic potential hitherto unexplored due to its narrow therapeutic toxic ratio. The aim of the present
E Perucca et al.
European journal of drug metabolism and pharmacokinetics, 20(4), 301-305 (1995-10-01)
The comparative pharmacokinetic and bioavailability profile of two different formulations (tablets and capsules) of thiocolchicoside was investigated in 8 healthy male volunteers after administration of single oral 8 mg doses. Plasma samples were assayed by a capillary gas chromatography--mass spectrometry
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