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SML0954

Sigma-Aldrich

Thiocolchicine

≥97% (HPLC)

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C22H25NO5S
Numero CAS:
2730-71-4
Peso molecolare:
415.50
Numero CE:
220-346-8
Codice UNSPSC:
12352200
NACRES:
NA.77

Livello qualitativo

100

Saggio

≥97% (HPLC)

Forma fisica

powder

Colore

white to beige

Solubilità

DMSO: 10 mg/mL, clear

Temperatura di conservazione

−20°C

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
CMEGANPVAXDBPL-INIZCTEOSA-N

Azioni biochim/fisiol

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

Avvertenze

Danger

Indicazioni di pericolo

H300 + H330,H318,H340

Classi di pericolo

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

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Certificati d'analisi (COA)

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Dorota Bartusik et al.
Bioorganic chemistry, 38(1), 1-6 (2009-12-01)
It was shown, that cultured ex vivo human T-Lymphoblastoid (CEM) cells respond to synthesized thiocolchicine and fluorine thiocolchicine derivatives. The preparation of derivatives with substitution at C-3 and C-7 is described. All compounds were used at concentration from 1 nM
R M Chabin et al.
Biochemical and biophysical research communications, 161(2), 544-550 (1989-06-15)
Thiocolchicine, a colchicine analog in which the C-10 methoxy is replaced with a thiomethyl moiety, was shown to bind with high affinity to the colchicine site on tubulin (Ka = 1.07 +/- 0.14 x 10(6) M-1 at 23 degrees C).
R De Vincenzo et al.
Oncology research, 11(3), 145-152 (1999-10-20)
Three new 7-0-substituted deacetamidothiocolchicine derivatives have been evaluated for their antitumor activity against various human tumor cell lines, some of which express the multidrug resistance (MDR) phenotype, for their impact on the cell cycle and their binding to tubulin. Colchicine
Bruno Danieli et al.
The Journal of organic chemistry, 71(7), 2848-2853 (2006-03-25)
A dynamic combinatorial library of thiocolchicine-podophyllotoxin derivatives based on the disulfide bond exchange reaction is described. The influence of a biological target on the composition of the reaction mixture has been demonstrated. Use of high-resolution ESI mass spectrometry to evaluate
A Muzaffar et al.
Journal of medicinal chemistry, 33(2), 567-571 (1990-02-01)
Esterification of the phenolic group in 3-demethylthiocolchicine and exchange of the N-acetyl group with other N-acyl groups or a N-carbalkoxy group afforded many compounds which showed superior activity over the parent drug as inhibitors of tubulin polymerization and of the
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