Synthesis and tubulin interaction of thiocolchicines containing an isothiocyanato group. Synthesis of C(2)-deuterated and C(2)-14C-labeled 7-isothiocyanatodeacetamidothiocolchicine

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Title:Synthesis and tubulin interaction of thiocolchicines containing an isothiocyanato group. Synthesis of C(2)-deuterated and C(2)-14C-labeled 7-isothiocyanatodeacetamidothiocolchicine
Creators:
Muzaffar, Anjum
Hamel, Ernest
Bai, Rouli
Brossi, Arnold
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 11, pp. 2306-2312

Abstract

Synthesis of isothiocyanato substituted thiocolchicines <i>XI - XIV</i> is described. Introduction of an isotope label is demonstrated with the deuterated isothiocyanate <i>XII</i> and the <sup>14</sup>C-labeled analog <i>XIII</i>. These isothiocyanates inhibit tubulin polymerization at low concentration. In addition, the <sup>14</sup>C-labeled <i>XIII</i> forms covalent bond(s) with tubulin. Unfortunately, the covalent reaction while rapid, is not inhibited by preincubation of tubulin with colchicine. The covalent interaction of <i>XIII</i> with tubulin thus appears to be nonspecific, limiting its use as a marker of the colchicine binding site on tubulin.

Title:Synthesis and tubulin interaction of thiocolchicines containing an isothiocyanato group. Synthesis of C(2)-deuterated and C(2)-14C-labeled 7-isothiocyanatodeacetamidothiocolchicine
Creators:
Muzaffar, Anjum
Hamel, Ernest
Bai, Rouli
Brossi, Arnold
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:56
Number:11
Page Range:pp. 2306-2312
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19912306UNSPECIFIED
ID Code:5160
Item Type:Article
Deposited On:22 Feb 2010 11:32
Last Modified:22 Feb 2010 10:32

Citation

Muzaffar, Anjum; Hamel, Ernest; Bai, Rouli; Brossi, Arnold (1991) Synthesis and tubulin interaction of thiocolchicines containing an isothiocyanato group. Synthesis of C(2)-deuterated and C(2)-14C-labeled 7-isothiocyanatodeacetamidothiocolchicine. Collection of Czechoslovak Chemical Communications, 56 (11). pp. 2306-2312. ISSN 0010-0765

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