Antimitotic activity on sea urchin embryonic cells of seven antiparasitic Morita-Baylis-Hillman adducts: a potential new class of anticancer drugs

Med Chem. 2012 Nov;8(6):1003-11. doi: 10.2174/1573406411208061003.


In the present work we described improvements in the 1-7 antiparasitic Morita-Baylis-Hillman Adducts synthesis and their antimitotic activity on sea urchin embryonic cells. The 2-[Hydroxy(2-nitrophenyl)methyl]acrylonitrile (1) and 2-[Hydroxy(4-bromophenyl) methyl]acrylonitrile (4) were the most effective compounds to block the progression to embryonic morula stage (EC(50) = 75.8 μM and 72.6 μM, respectively). Compounds 1 and 4 were also effective in blocking the first cell division but to a lesser extent. The 2-[Hydroxy(pyridin-4-yl)methyl]acrylonitrile (7) exhibited a strong inhibition of cell divisions and progression to the first cleavage and morula stage. Fluorescent dye extrusion assay suggests that these adducts are not ABC protein substrates, which confers an additional interest in these new class of potential anticancer drugs.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antimitotic Agents / chemical synthesis*
  • Antimitotic Agents / chemistry
  • Antimitotic Agents / pharmacology*
  • Antiparasitic Agents / chemical synthesis*
  • Antiparasitic Agents / chemistry
  • Antiparasitic Agents / pharmacology*
  • Cell Division / drug effects
  • Chemistry Techniques, Synthetic
  • Embryo, Nonmammalian / cytology*
  • Leishmania / drug effects
  • Morula / cytology
  • Morula / drug effects
  • Sea Urchins / embryology*


  • Antimitotic Agents
  • Antiparasitic Agents