Synthesis of 14C labelled electrophilic ligands of the colchicine binding site of tubulin: Chloroacetates of demethylthiocolchicines and of N-acetylcolchinol; isothiocyanate of 9-deoxy-N-acetylcolchinol
✍ Scribed by Olivier Boyé; Zelleka Getahun; Surinder Grover; Ernest Hamel; Arnold Brossi
- Publisher
- John Wiley and Sons
- Year
- 1993
- Tongue
- French
- Weight
- 334 KB
- Volume
- 33
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
Abstract
^14^C‐Chloroacetates of 2‐demethylthiocolchicine 7 (specific activity 55.0 mCi/mmol, radiochemical yield 26.1%), and of 3‐demethylthiocolchicine 8 (specific activity 55.0 mCi/mmol, radiochemical yield 5.7%) were synthesized and found to covalently bind with high specificity to the β‐subunit of tubulin. The ^14^C‐chloroacetate of N‐acetylcolchinol 5 (specific activity 56.0 mCi/mmol, radiochemical yield 7.8%) and the ^14^C‐isothiocyanate 6 (specific activity 50.0 mCi/mmol, radiochemical yield 32%) were also prepared and found to react covalently with tubulin but in a nonspecific manner. With the radiolabelled chloroacetates 7 and 8 two compounds are now available to further characterize the colchicine binding site on the β subunit of tubulin.