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SML0954

Sigma-Aldrich

Thiocolchicine

≥97% (HPLC)

Synonym(e):

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

Empirische Formel (Hill-System):
C22H25NO5S
CAS-Nummer:
2730-71-4
Molekulargewicht:
415.50
EG-Nummer:
220-346-8
UNSPSC-Code:
12352200
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥97% (HPLC)

Form

powder

Farbe

white to beige

Löslichkeit

DMSO: 10 mg/mL, clear

Lagertemp.

−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

InChIKey

CMEGANPVAXDBPL-INIZCTEOSA-N

Biochem./physiol. Wirkung

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

Signalwort

Danger

Gefahreneinstufungen

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

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (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).
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
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
Recent progress in structure-activity relationship studies on the anticancer drug colchicine and its analogues.
Xian-dao Pan et al.
Yao xue xue bao = Acta pharmaceutica Sinica, 37(10), 821-827 (2003-02-06)
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