Design, synthesis, and biological evaluation of biotinylated colchicine derivatives as potential antitumor agents

J Enzyme Inhib Med Chem. 2022 Dec;37(1):411-420. doi: 10.1080/14756366.2021.2013832.

Abstract

Chemical drug design based on the biochemical characteristics of cancer cells has become an important strategy for discovering new anti-tumour drugs to improve tumour targeting effects and reduce off-target toxicities. Colchicine is one of the most prominent and historically microtubule-targeting drugs, but its clinical applications are hindered by notorious adverse effects. In this study, we presented a novel tumour-specific conjugate 9 that consists of deacetylcolchicine (Deac), biotin, and a cleavable disulphide linker. 9 was found to exhibit potent anti-tumour activity and exerted higher selectivity between tumour and nontarget cells than Deac. The targeting moiety biotin might enhance the transport capability and selectivity of 9 to tumour cells via biotin receptor-mediated endocytosis. The tubulin polymerisation activity of 9 (with DTT) was close to the parent drug Deac. These preliminary results suggested that 9 is a high potency and reduced toxicity antitumor agent and worthy of further investigation.

Keywords: Colchicine; adverse effects; biotin; conjugate; disulphide bond.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Biotin / chemistry
  • Biotin / pharmacology
  • Biotinylation
  • Cell Proliferation / drug effects
  • Cells, Cultured
  • Colchicine / chemical synthesis
  • Colchicine / chemistry
  • Colchicine / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Design*
  • Drug Screening Assays, Antitumor
  • Humans
  • Mice
  • Molecular Structure
  • Polymerization / drug effects
  • Structure-Activity Relationship
  • Tubulin / metabolism
  • Tubulin Modulators / chemical synthesis
  • Tubulin Modulators / chemistry
  • Tubulin Modulators / pharmacology*

Substances

  • Antineoplastic Agents
  • Tubulin
  • Tubulin Modulators
  • Biotin
  • Colchicine

Grants and funding

We gratefully acknowledge the National Natural Science Foundation of China [81673293 and 81602969]. This work was also supported by the Program for Innovative Research Team of the Ministry of Education.