Synthesis and evaluation of biological properties of ferrocenyl-podophyllotoxin conjugates

Dalton Trans. 2017 Aug 22;46(33):10847-10858. doi: 10.1039/c7dt02107k.

Abstract

Three types, esters, amides and 1,2,3-triazoles, of ferrocenyl-podophyllotoxin conjugates were synthesised, and their anticancer activity was evaluated. We observed that the most potent ferrocenyl derivatives were esters. Esters 15, 16 and 17 acted in a similar way to podophyllotoxin, i.e. reduced the number of G1 phase cells and induced G2/M blockage, while esters 14 and 18 and amide 19 blocked cells in S phase in a similar manner to etoposide.

MeSH terms

  • Amides / chemistry
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / metabolism
  • Antineoplastic Agents / pharmacology*
  • Cell Cycle / drug effects
  • Cell Line, Tumor
  • Chemistry Techniques, Synthetic
  • Esterases / metabolism
  • Ferrous Compounds / chemistry*
  • Humans
  • Metallocenes / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Podophyllotoxin / chemical synthesis*
  • Podophyllotoxin / chemistry
  • Podophyllotoxin / metabolism
  • Podophyllotoxin / pharmacology*
  • Protein Multimerization / drug effects
  • Protein Structure, Quaternary
  • Triazoles / chemistry
  • Tubulin / chemistry

Substances

  • Amides
  • Antineoplastic Agents
  • Ferrous Compounds
  • Metallocenes
  • Triazoles
  • Tubulin
  • Esterases
  • Podophyllotoxin
  • ferrocene