Discovery of novel polyamide-pyrrolobenzodiazepine hybrids for antibody-drug conjugates

Bioorg Med Chem Lett. 2022 Sep 15:72:128876. doi: 10.1016/j.bmcl.2022.128876. Epub 2022 Jul 3.

Abstract

Pyrrolobenzodiazepine (PBD) dimers are well-known highly potent antibody drug conjugate (ADC) payloads. The corresponding PBD monomers, in contrast, have received much less attention from the ADC community. We prepared several novel polyamide-linked PBD monomers and evaluated their utility as ADC payloads. The unconjugated polyamide-PBD hybrids exhibited potent antiproliferative activity (IC50 range: 10-11-10-8 M) against a variety of HER2-expressing cancer cell lines. Several peptide-linked variants of the lead compound were prepared and conjugated to trastuzumab to afford ADCs with drug-to-antibody (DAR) ratios ranging from 3 to 5. The ADCs exhibited antigen-dependent cytotoxicity in vitro and potently suppressed tumor xenograft growth in vivo in a target-dependent manner. Moreover, the ADCs were well-tolerated in both mouse and rat. This work demonstrates for the first time that PBD polyamide hybrids can serve as effective ADC payloads.

Keywords: ADC; Antibody-drug conjugate; Mono-alkylator; PBD; Pyrrolobenzodiazepine.

MeSH terms

  • Animals
  • Antineoplastic Agents* / pharmacology
  • Benzodiazepines
  • Cell Line, Tumor
  • Humans
  • Immunoconjugates* / pharmacology
  • Immunoconjugates* / therapeutic use
  • Mice
  • Nylons / pharmacology
  • Pyrroles
  • Rats
  • Xenograft Model Antitumor Assays

Substances

  • Antineoplastic Agents
  • Immunoconjugates
  • Nylons
  • Pyrroles
  • pyrrolo(2,1-c)(1,4)benzodiazepine
  • Benzodiazepines