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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

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.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
R Brecht et al.
Bioorganic & medicinal chemistry, 8(3), 557-562 (2000-03-25)
Several B-ring variations of O-methyl androbiphenyline (8), newly accessible from (-)-(M,7S)-colchicine via photooxygenation and subsequent endoperoxide-transformation, were synthesized and evaluated for their inhibitory effects on tubulin assembly in vitro. The amino-allocolchicinoid (9), a key compound in this study, was transformed
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