A novel mertansine conjugate for acid-reversible targeted drug delivery validated through the Avidin-Nucleic-Acid-NanoASsembly platform

Nanomedicine. 2024 Nov:62:102784. doi: 10.1016/j.nano.2024.102784. Epub 2024 Sep 3.

Abstract

In targeted cancer therapy, antibody-drug-conjugates using mertansine (DM1)-based cytotoxic compounds rely on covalent bonds for drug conjugation. Consequently, the cytotoxic DM1 derivative released upon their proteolytic digestion is up to 1000-fold less potent than DM1 and lacks a bystander effect. To overcome these limitations, we developed a DM1 derivative (keto-DM1) suitable for bioconjugation through an acid-reversible hydrazone bond. Its acid-reversible hydrazone conjugate with biotin (B-Hz-DM1) was generated and tested for efficacy using the cetuximab-targeted Avidin-Nucleic-Acid-NanoASsembly (ANANAS) nanoparticle (NP) platform. NP-tethered B-Hz-DM1 is stable at neutral pH and releases its active moiety only in endosome/lysosome mimicking acidic pH. In vitro, the NP/Cetux/B-Hz-DM1 assembly showed high potency on MDA-MB231 breast cancer cells. In vivo both B-Hz-DM1 and NP/Cetux/B-Hz-DM1 reduced tumor growth. A significantly major effect was exerted by the nanoformulation, associated with an increased in situ tumor cell death. Keto-DM1 is a promising acid-reversible mertansine derivative for targeted delivery in cancer therapy.

Keywords: Avidin-Nucleic-Acid-NanoASsembly; Avidin-biotin; DM1; Mertansine; Reversible conjugates; Targeted therapeutics; cancer.

MeSH terms

  • Animals
  • Avidin* / chemistry
  • Breast Neoplasms / drug therapy
  • Breast Neoplasms / pathology
  • Cell Line, Tumor
  • Drug Delivery Systems*
  • Female
  • Humans
  • Hydrogen-Ion Concentration
  • Immunoconjugates / chemistry
  • Immunoconjugates / pharmacology
  • Maytansine* / chemistry
  • Maytansine* / pharmacology
  • Mice
  • Nanoparticles / chemistry
  • Nucleic Acids / chemistry

Substances

  • Maytansine
  • Avidin
  • Nucleic Acids
  • Immunoconjugates