Antibody-maytansinoid conjugates designed to bypass multidrug resistance

Cancer Res. 2010 Mar 15;70(6):2528-37. doi: 10.1158/0008-5472.CAN-09-3546. Epub 2010 Mar 2.

Abstract

Conjugation of cytotoxic compounds to antibodies that bind to cancer-specific antigens makes these drugs selective in killing cancer cells. However, many of the compounds used in such antibody-drug conjugates (ADC) are substrates for the multidrug transporter MDR1. To evade the MDR1-mediated resistance, we conjugated the highly cytotoxic maytansinoid DM1 to antibodies via the maleimidyl-based hydrophilic linker PEG(4)Mal. Following uptake into target cells, conjugates made with the PEG(4)Mal linker were processed to a cytotoxic metabolite that was retained by MDR1-expressing cells better than a metabolite of similar conjugates prepared with the nonpolar linker N-succinimidyl-4-(maleimidomethyl)cyclohexane-1-carboxylate (SMCC). In accord, PEG(4)Mal-linked conjugates were more potent in killing MDR1-expressing cells in culture. In addition, PEG(4)Mal-linked conjugates were markedly more effective in eradicating MDR1-expressing human xenograft tumors than SMCC-linked conjugates while being tolerated similarly, thus showing an improved therapeutic index. This study points the way to the development of ADCs that bypass multidrug resistance.

MeSH terms

  • ATP Binding Cassette Transporter, Subfamily B
  • ATP Binding Cassette Transporter, Subfamily B, Member 1 / biosynthesis
  • ATP Binding Cassette Transporter, Subfamily B, Member 1 / metabolism
  • Adenocarcinoma / drug therapy
  • Adenocarcinoma / metabolism
  • Animals
  • Antigens, Neoplasm / chemistry
  • Antigens, Neoplasm / immunology
  • Carcinoma, Renal Cell / drug therapy
  • Carcinoma, Renal Cell / metabolism
  • Cell Adhesion Molecules / chemistry
  • Cell Adhesion Molecules / immunology
  • Cell Line, Tumor
  • Colonic Neoplasms / drug therapy
  • Colonic Neoplasms / metabolism
  • Drug Resistance, Multiple
  • Drug Resistance, Neoplasm
  • Epithelial Cell Adhesion Molecule
  • Female
  • Humans
  • Immunotoxins / chemistry
  • Immunotoxins / pharmacokinetics
  • Immunotoxins / pharmacology*
  • Kidney Neoplasms / drug therapy
  • Kidney Neoplasms / metabolism
  • Maleimides / chemistry
  • Maytansine / analogs & derivatives*
  • Maytansine / chemistry
  • Maytansine / pharmacokinetics
  • Maytansine / pharmacology
  • Mice
  • Mice, SCID
  • Polyethylene Glycols / chemistry

Substances

  • 15-amino-4,7,10,13-tetraoxapentadecanoic acid
  • ABCB1 protein, human
  • ATP Binding Cassette Transporter, Subfamily B
  • ATP Binding Cassette Transporter, Subfamily B, Member 1
  • Antigens, Neoplasm
  • Cell Adhesion Molecules
  • EPCAM protein, human
  • Epithelial Cell Adhesion Molecule
  • Immunotoxins
  • Maleimides
  • Maytansine
  • Polyethylene Glycols
  • N-(4-carboxycyclohexylmethyl)maleimide N-hydroxysuccinimide ester