Extended scaffold glucuronides: en route to the universal synthesis of O-aryl glucuronide prodrugs

Org Biomol Chem. 2019 Jul 24;17(29):6970-6974. doi: 10.1039/c9ob01384a.

Abstract

We demonstrate that an extended scaffold based on a self-immolative linker (SIL) enables the universal production of O-aryl glucuronide prodrugs: high yield glucuronidation is performed on a precursor substrate (SIL) and the subsequent drug conjugation proceeds via less challenging chemical reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Glucuronides / chemical synthesis*
  • Glucuronides / chemistry
  • Glucuronides / pharmacology
  • HeLa Cells
  • Humans
  • Molecular Structure
  • Prodrugs / chemical synthesis*
  • Prodrugs / chemistry
  • Prodrugs / pharmacology
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Glucuronides
  • Prodrugs