Synthesis, physicochemical properties and in vitro cytotoxicity of nicotinic acid ester prodrugs intended for pulmonary delivery using perfluorooctyl bromide as vehicle

Int J Pharm. 2008 Apr 2;353(1-2):35-44. doi: 10.1016/j.ijpharm.2007.11.011. Epub 2007 Nov 17.

Abstract

This study explores perfluorooctyl bromide (PFOB) as a potential vehicle for the pulmonary delivery of a series of prodrugs of nicotinic acid using cell culture studies. The prodrugs investigated have PFOB-water (logK(p)=0.78 to >2.2), perfluoromethylcyclohexane-toluene (logK(p)=-2.62 to 0.13) and octanol-water (logK(p)=0.90-10.2) partition coefficients spanning several orders of magnitude. In confluent NCI-H358 human lung cancer cells, the toxicity of prodrugs administered in culture medium or PFOB depends on the medium of administration, with EC20's above 8 mM and 2.5 mM for culture medium and PFOB, respectively. Short-chain nicotinates administered both in PFOB and medium increase cellular NAD/NADP levels at 1mM nicotinate concentrations. Long-chain nicotinates, which could not be administered in medium due to their poor aqueous solubility, increased NAD/NADP levels if administered in PFOB at concentrations > or =10 mM. These findings suggest that even highly lipophilic prodrugs can partition out of the PFOB phase into cells, where nicotinic acid is released and converted to NAD. Thus, PFOB may be a novel and biocompatible vehicle for the delivery of lipophilic prodrugs of nicotinic acid and other drugs directly to the lung of laboratory animals and humans.

Publication types

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

MeSH terms

  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Fluorocarbons / administration & dosage*
  • Humans
  • Hydrocarbons, Brominated
  • Lung / metabolism*
  • NAD / analysis
  • NADP / analysis
  • Nicotinic Acids / administration & dosage*
  • Nicotinic Acids / chemical synthesis
  • Nicotinic Acids / chemistry
  • Nicotinic Acids / pharmacology
  • Pharmaceutical Vehicles
  • Prodrugs / administration & dosage*
  • Prodrugs / chemical synthesis
  • Prodrugs / chemistry
  • Prodrugs / pharmacology
  • Solubility

Substances

  • Fluorocarbons
  • Hydrocarbons, Brominated
  • Nicotinic Acids
  • Pharmaceutical Vehicles
  • Prodrugs
  • NAD
  • NADP
  • perflubron