Synthesis and binding to tubulin of colchicine spin probes.

  title={Synthesis and binding to tubulin of colchicine spin probes.},
  author={P. Sharma and A. Brossi and J. Silverton and C. Chignell},
  journal={Journal of medicinal chemistry},
  volume={27 12},
Spin probes of deacetylcholchicine (1), 4-(hydroxymethyl)colchicine (2), and colchifoline (3) have been synthesized to study the binding site for colchicine on tubulin. Acylation of 1-3 with (+/-)-2,2,5,5-tetramethyl-1-pyrrolidinyloxy-3-carboxylic acid (4) afforded diastereomeric mixtures of the esters 5-8 and the amides 9 and 10. Pure diastereomers of 3 were synthesized with 4a and 4b, which inhibited the binding of colchicine by 60%. In the presence of calf brain microtubular protein, the… Expand
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