First orally bioavailable prodrug of proteolysis targeting chimera (PROTAC) degrades cyclin-dependent kinases 2/4/6 in vivo

Eur J Med Chem. 2021 Jan 1:209:112903. doi: 10.1016/j.ejmech.2020.112903. Epub 2020 Oct 9.

Abstract

A growing number of reports suggested that the inhibitor targeting cyclin-dependent kinases (CDK) 2/4/6 can act as a more feasible chemotherapy strategy. In the present paper, a novel PROTAC molecule was developed based on the structure of Ribociclib's derivative. In malignant melanoma cells, the degrader can not only degrade CDK 2/4/6 simultaneously and effectively, but also remarkably induce cell cycle arrest and apoptosis of melanoma cells. Moreover, PROTAC molecules with CRBN ligands always have poor oral bioavailability. We developed the orally bioavailable prodrug for the first time. It would provide general solution for oral administration of the PROTAC molecules, derived from CRBN ligands, for animal test conveniently.

Keywords: Anti-tumor; CDK 2/4/6; Orally bioavailable prodrug; PROTAC.

MeSH terms

  • Administration, Oral
  • Aminopyridines* / chemical synthesis
  • Aminopyridines* / pharmacokinetics
  • Animals
  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / pharmacokinetics
  • Apoptosis / drug effects
  • Cell Cycle Checkpoints / drug effects
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cyclin-Dependent Kinases* / metabolism
  • Humans
  • Mice
  • Mice, Inbred C57BL
  • Neoplasms, Experimental
  • Prodrugs* / chemical synthesis
  • Prodrugs* / pharmacokinetics
  • Proteolysis*
  • Purines* / chemical synthesis
  • Purines* / pharmacokinetics
  • Structure-Activity Relationship
  • Transcription Factors / metabolism

Substances

  • Aminopyridines
  • Antineoplastic Agents
  • Cyclin-Dependent Kinases
  • Prodrugs
  • Purines
  • ribociclib
  • Transcription Factors