Ultrasmall dual-modality silica nanoparticle drug conjugates: Design, synthesis, and characterization

Bioorg Med Chem. 2015 Nov 15;23(22):7119-30. doi: 10.1016/j.bmc.2015.09.050. Epub 2015 Oct 11.

Abstract

The physicochemical design and synthesis of effective cancer-directed and particle-based nanotherapeutic imaging agents remains a challenging task. Of critical importance is the ability to demonstrate maximum delivery, retention, and treatment efficacy for platforms designed to deposit their cargo at sites of disease without attendant dose-limiting toxicity. In this work, we describe dual-modality nanoparticle drug conjugates (NDCs) which utilize protease sensitive linkers to attached drug compounds and imaging labels to a clinically translated class of ultrasmall silica nanoparticle (C' dots). We describe the synthesis and characterization of these linker-drug constructs. Linkers incorporating dipeptide enzyme substrates are attached to analogs of a prototypical epidermal growth factor receptor tyrosine kinase inhibitor (EGFR-TKI), through a cleavable amide bond or para-aminobenzyloxycarbonyl (PABC) group. These constructs are conjugated onto C' dots leading to the desired NDCs. These NDCs exhibit fast and predictable release kinetics in the presence of model proteases, and are stable in various biological media. Finally, in vitro assays show NDCs to be highly active in reducing phosphorylated EGFR levels in H1650 cells, a human tumor-derived cell line. The data suggests that NDCs exhibit desirable properties that warrant further development toward oncological therapy.

Keywords: Cancer; Drug conjugate; Drug delivery; Kinase inhibitor; Nanoparticle.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Chromatography, High Pressure Liquid
  • Drug Carriers / chemical synthesis*
  • Drug Carriers / chemistry
  • Drug Design*
  • ErbB Receptors / antagonists & inhibitors
  • ErbB Receptors / metabolism
  • Gefitinib
  • Humans
  • Nanoparticles / chemistry*
  • Peptide Hydrolases / metabolism
  • Phosphorylation
  • Protein Binding
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / metabolism
  • Quinazolines / chemistry
  • Quinazolines / metabolism
  • Silicon Dioxide / chemistry*

Substances

  • Drug Carriers
  • Protein Kinase Inhibitors
  • Quinazolines
  • Silicon Dioxide
  • ErbB Receptors
  • Peptide Hydrolases
  • Gefitinib