Structural Characterization of Cross-Linked Species in Trastuzumab Emtansine (Kadcyla)

Bioconjug Chem. 2016 Sep 21;27(9):2037-47. doi: 10.1021/acs.bioconjchem.6b00316. Epub 2016 Aug 9.

Abstract

The antibody-drug conjugate, trastuzumab emtansine (Kadcyla), is produced by attachment of the antitubulin drug, DM1, to lysine amines via a heterobifunctional linker, SMCC (succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate). Following the reaction of the N-hydroxysuccinimide activated linker with antibody lysines to produce a linker-modified intermediate (Tmab-MCC), DM1 is added to yield the desired product. In addition to the expected distribution of drug-linked forms (from 0 to 8), mass spectrometry also demonstrates the presence of a second distribution shifted by about +222 Da. This series is consistent with the presence of a population containing a bound linker without DM1 ("unconjugated linker"). Extended characterization of trastuzumab emtansine was performed using capillary isoelectic focusing, CE-SDS, peptide mapping, and LC/MS following (18)O labeling of peptide digests to identify this family of product variants. These studies demonstrate that the presence of these +222 Da species is due to an unexpected reaction of the maleimide moiety in the MCC linker with antibody lysine residues to produce cross-linked species that cannot conjugate to DM1.

MeSH terms

  • Ado-Trastuzumab Emtansine
  • Amino Acid Sequence
  • Antibodies, Monoclonal, Humanized / chemistry*
  • Lysine / chemistry
  • Maleimides / chemistry
  • Maytansine / analogs & derivatives*
  • Maytansine / chemistry
  • Models, Molecular
  • Peptides / chemistry*
  • Protein Structure, Secondary
  • Trastuzumab

Substances

  • Antibodies, Monoclonal, Humanized
  • Maleimides
  • Peptides
  • Maytansine
  • N-(4-carboxycyclohexylmethyl)maleimide N-hydroxysuccinimide ester
  • Lysine
  • Trastuzumab
  • Ado-Trastuzumab Emtansine