Synthesis of a heterotrifunctional linker for the site-specific preparation of antibody-drug conjugates with two distinct warheads

Bioorg Med Chem Lett. 2018 Dec 15;28(23-24):3617-3621. doi: 10.1016/j.bmcl.2018.10.043. Epub 2018 Oct 26.

Abstract

Codelivery of multiple therapeutic agents with different anticancer mechanisms can overcome drug resistance as well as generate additive or synergistic anticancer effects that may enhance the antitumor efficacy. Antibody-drug conjugates (ADCs) can be used for highly specific delivery of multiple therapeutic agents with different anticancer mechanisms, though more research is required towards designing flexible platforms on which dual drug ADCs could be prepared. Herein, we describe the synthesis of a heterotrifunctional linker that could be used to construct flexible platforms for preparing dual-cytotoxic drug conjugates in a site-specific manner. As a proof of concept, we synthesized dual drug ADCs carrying monomethyl auristain E (MMAE, tubulin polymerization inhibitor) and pyrrolobenzodiazepine dimer (PBD, DNA minor groove alkylator). We then evaluated the dual drug ADCs for in vitro efficacy and confirmed the dual mechanism of action.

Keywords: Antibody−drug conjugates; Dual-warheads antibody-drug conjugates; Heterotrifunctional linkers; Monomethyl auristain E (MMAE); Pyrrolobenzodiazepine dimers (PBDs).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminobenzoates / chemistry
  • Antibodies, Monoclonal / chemistry
  • Antineoplastic Agents, Alkylating / chemistry
  • Benzodiazepines / chemistry
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Click Chemistry
  • Humans
  • Immunoconjugates / chemistry*
  • Immunoconjugates / pharmacology
  • Oligopeptides / chemistry
  • Pyrroles / chemistry
  • Tubulin Modulators / chemistry*

Substances

  • Aminobenzoates
  • Antibodies, Monoclonal
  • Antineoplastic Agents, Alkylating
  • Immunoconjugates
  • Oligopeptides
  • Pyrroles
  • Tubulin Modulators
  • auristatin
  • pyrrolo(2,1-c)(1,4)benzodiazepine
  • Benzodiazepines