Synthesis and evaluation of hydrophilic linkers for antibody-maytansinoid conjugates

J Med Chem. 2011 May 26;54(10):3606-23. doi: 10.1021/jm2002958. Epub 2011 May 4.

Abstract

The synthesis and biological evaluation of hydrophilic heterobifunctional cross-linkers for conjugation of antibodies with highly cytotoxic agents are described. These linkers contain either a negatively charged sulfonate group or a hydrophilic, noncharged PEG group in addition to an amine-reactive N-hydroxysuccinimide (NHS) ester and sulfhydryl reactive termini. These hydrophilic linkers enable conjugation of hydrophobic organic molecule drugs, such as a maytansinoid, at a higher drug/antibody ratio (DAR) than hydrophobic SPDB and SMCC linkers used earlier without triggering aggregation or loss of affinity of the resulting conjugate. Antibody-maytansinoid conjugates (AMCs) bearing these sulfonate- or PEG-containing hydrophilic linkers were, depending on the nature of the targeted cells, equally to more cytotoxic to antigen-positive cells and equally to less cytotoxic to antigen-negative cells than conjugates made with SPDB or SMCC linkers and thus typically displayed a wider selectivity window, particularly against multidrug resistant (MDR) cancer cell lines in vitro and tumor xenograft models in vivo.

MeSH terms

  • Animals
  • Antibodies / chemistry*
  • Chemistry, Pharmaceutical / methods
  • Drug Design
  • Drug Resistance, Multiple
  • Drug Resistance, Neoplasm
  • Drug Screening Assays, Antitumor
  • Humans
  • Immunoconjugates / chemistry*
  • Maytansine / chemistry*
  • Mice
  • Models, Chemical
  • Neoplasm Transplantation
  • Polyethylene Glycols / chemistry
  • Succinimides / chemistry
  • Sulfones / chemistry

Substances

  • Antibodies
  • Immunoconjugates
  • Succinimides
  • Sulfones
  • Maytansine
  • Polyethylene Glycols
  • N-hydroxysuccinimide