CBTF: new amine-to-thiol coupling reagent for preparation of antibody conjugates with increased plasma stability

Bioconjug Chem. 2015 Feb 18;26(2):197-200. doi: 10.1021/bc500610g. Epub 2015 Jan 23.

Abstract

Amine-to-thiol coupling is the most common route for the preparation of antibody-drug conjugates (ADC). It is usually achieved by using heterobifunctional reagents possessing an activated ester at one end and a maleimide group at the other. However, maleimide-based conjugates were recently revealed to have limited stability in blood circulation, which can compromise therapeutic efficacy of the conjugate. To address this issue, we have developed a heterobifunctional reagent, sodium 4-((4-(cyanoethynyl)benzoyl)oxy)-2,3,5,6-tetrafluorobenzenesulfonate (CBTF), for amine-to-thiol coupling. It comprises a recently described 3-arylpropionitrile (APN) function in replacement of maleimide and allows for the preparation of remarkably stable conjugates. A series of antibody-dye conjugates have been prepared using this reagent and shown superior stability in human blood plasma compared to maleimide-derived conjugates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Benzene Derivatives / chemistry*
  • Cell Line
  • Cross-Linking Reagents / chemistry*
  • Halogenation
  • Humans
  • Immunoconjugates / blood
  • Immunoconjugates / chemistry*
  • Maleimides / chemistry
  • Sulfhydryl Compounds / chemistry*

Substances

  • Amines
  • Benzene Derivatives
  • Cross-Linking Reagents
  • Immunoconjugates
  • Maleimides
  • Sulfhydryl Compounds
  • maleimide