Molecularly defined antibody conjugation through a selenocysteine interface

Biochemistry. 2009 Dec 22;48(50):12047-57. doi: 10.1021/bi901744t.

Abstract

Antibody conjugates have broad utility in basic, preclinical, and clinical applications. Conventional antibody conjugation through the amine group of lysine or the thiol group of cysteine residues yields heterogeneous products of undefined stoichiometry and considerable batch-to-batch variability. To preserve the two hallmarks of the antibody molecule, precision and predictability, methods that enable site-specific antibody conjugation are in high demand. On the basis of a mammalian cell expression system, we describe the utilization of the 21st natural amino acid selenocysteine for the generation of IgG and Fab molecules with unique nucleophilic reactivity that affords site-specific conjugation to electrophilic derivatives of biotin, fluorescein, and poly(ethylene glycol). The resulting antibody conjugates were found to fully retain their antigen binding capability and, in the case of IgG, the ability to mediate effector functions. Gain of function was demonstrated in vitro and in vivo. While these antibody conjugates are relevant for a variety of proteomic, diagnostic, and therapeutic applications, they also constitute a proof of principle for the generation of molecularly defined antibody-drug conjugates and radioimmunoconjugates. Compared to other site-specific antibody conjugation methods, selenocysteine interface technology (i) only involves a minor modification at the C-terminus that does not interfere with disulfide bridges, (ii) does not require activation, and (iii) generates unique 1:1 stoichiometries of biological and chemical components. Collectively, our method affords the generation of highly defined antibody conjugates with broad utility from proteomic applications to therapeutic intervention.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, N.I.H., Intramural

MeSH terms

  • Animals
  • Antibodies, Monoclonal / administration & dosage
  • Antibodies, Monoclonal / chemistry*
  • Antibodies, Monoclonal / genetics
  • Antibodies, Monoclonal, Murine-Derived
  • Cell Line
  • Cell Line, Tumor
  • Cystine / administration & dosage
  • Cystine / analogs & derivatives*
  • Cystine / chemistry
  • Cystine / genetics
  • Histidine / administration & dosage
  • Histidine / chemistry
  • Histidine / genetics
  • Humans
  • Immunoconjugates / administration & dosage
  • Immunoconjugates / chemistry*
  • Immunoconjugates / genetics
  • Immunoglobulin Fab Fragments / administration & dosage
  • Immunoglobulin Fab Fragments / chemistry
  • Immunoglobulin Fc Fragments / chemistry
  • Immunoglobulin Fc Fragments / genetics
  • Immunoglobulin G / chemistry
  • Immunoglobulin G / genetics
  • Immunoglobulin Heavy Chains / chemistry
  • Immunoglobulin Variable Region / chemistry
  • Mice
  • Mice, Inbred C57BL
  • Mutant Chimeric Proteins / administration & dosage
  • Mutant Chimeric Proteins / chemistry
  • Organoselenium Compounds / administration & dosage
  • Organoselenium Compounds / chemistry*
  • Rituximab

Substances

  • Antibodies, Monoclonal
  • Antibodies, Monoclonal, Murine-Derived
  • Immunoconjugates
  • Immunoglobulin Fab Fragments
  • Immunoglobulin Fc Fragments
  • Immunoglobulin G
  • Immunoglobulin Heavy Chains
  • Immunoglobulin Variable Region
  • Mutant Chimeric Proteins
  • Organoselenium Compounds
  • selenocystine
  • Cystine
  • Rituximab
  • Histidine