Evaluation of atazanavir and darunavir interactions with lipids for developing pH-responsive anti-HIV drug combination nanoparticles

J Pharm Sci. 2014 Aug;103(8):2520-9. doi: 10.1002/jps.24046. Epub 2014 Jun 19.

Abstract

We evaluated two human immunodeficiency virus (HIV) protease inhibitors, atazanavir (ATV) and darunavir (DRV), for pH-dependent solubility, lipid binding, and drug release from lipid nanoparticles (LNPs). Both ATV and DRV incorporated into LNPs composed of pegylated and non-pegylated phospholipids with nearly 100% efficiency, but only ATV-LNPs formed stable lipid-drug particles and exhibited pH-dependent drug release. DRV-LNPs were unstable and formed mixed micelles at low drug-lipid concentrations, and thus are not suitable for lipid-drug particle development. When ATV-LNPs were prepared with ritonavir (RTV), a metabolic and cellular membrane exporter inhibitor, and tenofovir (TFV), an HIV reverse-transcriptase inhibitor, stable, scalable, and reproducible anti-HIV drug combination LNPs were produced. Drug incorporation efficiencies of 85.5 ± 8.2, 85.1 ± 7.1, and 6.1 ± 0.8% for ATV, RTV, and TFV, respectively, were achieved. Preliminary primate pharmacokinetic studies with these pH-responsive anti-HIV drug combination LNPs administered subcutaneously produced detectable plasma concentrations that lasted for 7 days for all three drugs. These anti-HIV LNPs could be developed as a long-acting targeted antiretroviral therapy.

Keywords: HIV; lipid-drug interactions; long acting; nanotechnology; pharmacokinetics; physical characterization; primate; stabilization; targeted drug delivery.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Adenine / administration & dosage
  • Adenine / analogs & derivatives*
  • Adenine / blood
  • Adenine / chemistry
  • Animals
  • Anti-HIV Agents / administration & dosage*
  • Anti-HIV Agents / blood
  • Anti-HIV Agents / chemistry
  • Atazanavir Sulfate
  • Darunavir
  • Delayed-Action Preparations / chemistry*
  • Drug Combinations
  • Drug Delivery Systems
  • Humans
  • Hydrogen-Ion Concentration
  • Lipids / chemistry*
  • Macaca nemestrina
  • Oligopeptides / administration & dosage*
  • Oligopeptides / blood
  • Oligopeptides / chemistry
  • Organophosphonates / administration & dosage*
  • Organophosphonates / blood
  • Organophosphonates / chemistry
  • Pyridines / administration & dosage*
  • Pyridines / blood
  • Pyridines / chemistry
  • Sulfonamides / administration & dosage*
  • Sulfonamides / blood
  • Sulfonamides / chemistry
  • Tenofovir

Substances

  • Anti-HIV Agents
  • Delayed-Action Preparations
  • Drug Combinations
  • Lipids
  • Oligopeptides
  • Organophosphonates
  • Pyridines
  • Sulfonamides
  • Atazanavir Sulfate
  • Tenofovir
  • Adenine
  • Darunavir