Acid-cleavable thiomaleamic acid linker for homogeneous antibody-drug conjugation

Chem Commun (Camb). 2013 Sep 25;49(74):8187-9. doi: 10.1039/c3cc45220d.

Abstract

In this communication we describe a novel acid-cleavable linker strategy for antibody-drug conjugation. Functional disulfide bridging of the single interchain disulfide bond of a trastuzumab Fab fragment yields a homogeneous antibody-drug conjugate bearing a thiomaleamic acid linker. This linker is stable at physiological pH and temperature, but quantitatively cleaves at lysosomal pH to release the drug payload.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antibodies, Monoclonal, Humanized / chemistry*
  • Disulfides / chemistry
  • Hydrogen-Ion Concentration
  • Maleates / chemistry*
  • Molecular Structure
  • Pharmaceutical Preparations / chemistry*
  • Temperature
  • Trastuzumab

Substances

  • Antibodies, Monoclonal, Humanized
  • Disulfides
  • Maleates
  • Pharmaceutical Preparations
  • thiomaleamic acid
  • Trastuzumab