Structure--antitubulin activity relationship in steganacin congeners and analogues. Inhibition of tubulin polymerization in vitro by (+/-)-isodeoxypodophyllotoxin

J Med Chem. 1980 May;23(5):546-9. doi: 10.1021/jm00179a014.

Abstract

A new series of 23 synthetic analogues of the naturally occurring antitumor lignan steganacin was tested for the inhibition of microtubule assembly in vitro. Interestingly, (+/-)-isopicrostegane (I50 = 5 microM) was found to be almost as active as (+/-)-steganacin(I50 = 3.5 microM). On the other hand, racemic isodeoxypodophyllotoxin has an inhibiting activity of microtubule assembly comparable to that of (-)-podophyllotoxin, whereas (-)-isodeoxypodophyllotoxin is totally inactive.

MeSH terms

  • Colchicine / metabolism
  • Depression, Chemical
  • Drugs, Chinese Herbal
  • Kinetics
  • Podophyllotoxin / analogs & derivatives*
  • Podophyllotoxin / chemical synthesis
  • Podophyllotoxin / pharmacology
  • Protein Binding
  • Structure-Activity Relationship
  • Tubulin / biosynthesis*

Substances

  • Drugs, Chinese Herbal
  • Tubulin
  • deoxypodophyllotoxin
  • Podophyllotoxin
  • Colchicine