Alkyl-Modified Oligonucleotides as Intercalating Vehicles for Doxorubicin Uptake via Albumin Binding

Mol Pharm. 2018 Feb 5;15(2):437-446. doi: 10.1021/acs.molpharmaceut.7b00805. Epub 2018 Jan 8.

Abstract

DNA-based drug delivery vehicles have displayed promise for the delivery of intercalating drugs. Here, we demonstrate that oligonucleotides modified with an alkyl chain can bind to human serum albumin, mimicking the natural binding of fatty acids. These alkyl-DNA-albumin complexes display excellent serum stability and are capable of strongly binding doxorubicin. Complexes are internalized by cells in vitro, trafficking to the mitochondria, and are capable of delivering doxorubicin with excellent efficiency resulting in cell death. However, the cellular localization of the delivered doxorubicin, and ultimately the complex efficacy, is dependent on the nature of the linker between the alkyl group and the oligonucleotide.

Keywords: albumin; cytotoxic; mitochondrial targeting; oligonucleotides; prodrug.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antibiotics, Antineoplastic / administration & dosage*
  • Apoptosis / drug effects
  • Doxorubicin / administration & dosage*
  • Drug Screening Assays, Antitumor
  • Drug Stability
  • Humans
  • Intercalating Agents / chemistry*
  • Intercalating Agents / metabolism
  • MCF-7 Cells
  • Mitochondria / metabolism
  • Neoplasms / drug therapy
  • Oligonucleotides / chemistry*
  • Oligonucleotides / metabolism
  • Pharmaceutical Vehicles / chemistry*
  • Pharmaceutical Vehicles / metabolism
  • Prodrugs / administration & dosage
  • Protein Binding
  • Serum Albumin, Human / metabolism

Substances

  • Antibiotics, Antineoplastic
  • Intercalating Agents
  • Oligonucleotides
  • Pharmaceutical Vehicles
  • Prodrugs
  • Doxorubicin
  • Serum Albumin, Human