HPLC-FLD determination of NBD-cholesterol, its ester and other metabolites in cellular lipid extracts

Biomed Chromatogr. 2013 Jul;27(7):910-5. doi: 10.1002/bmc.2881. Epub 2013 Mar 25.

Abstract

22-[N(-7-Nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-23,24-bisnor-5-cholen-3β-ol (NBD-cholesterol), a fluorescent cholesterol analog, was an extragenous cholesterol tracer used to study cholesterol absorption and metabolism in cultured cells. In order to measure free intracellular cholesterol and its esters, a precise and sensitive method employing high-performance liquid chromatography/fluorescence detection (HPLC-FLD) was developed for the first time. Method validation showed a limit of detection at 30 ng/mL. The calibration curve was linear within the range of 0.0625-10.0 µg/mL (r(2) = 0.999). Accuracy and precision were highlighted by good recovery and low variations. Apart from NBD-cholesteryl oleate, two additional cellular metabolites of NBD-cholesterol, probably an isomer and an oxidation product, were determined in the lipid extracts of Caco-2 human colon adenocarcinoma cells according to mass spectrometry. In AC29 mouse malignant mesothelioma cells overexpressing acyl-CoA:cholesterol acyltransferase-1 (ACAT1) or ACAT2, only the oxidized metabolite was detected. Using the newly developed method, YIC-C8-434, a known ACAT inhibitor, was shown to inhibit ACAT activity in Caco-2 cells, as well as in AC29/ACAT1 or AC29/ACAT2 cells. In conclusion, the sensitive and specific HPLC-FLD method is a powerful tool for simultaneous quantification of intracellular NBD-cholesterol and its oleoyl-ester.

MeSH terms

  • 4-Chloro-7-nitrobenzofurazan / analogs & derivatives*
  • 4-Chloro-7-nitrobenzofurazan / analysis
  • 4-Chloro-7-nitrobenzofurazan / chemistry
  • 4-Chloro-7-nitrobenzofurazan / metabolism
  • Animals
  • Caco-2 Cells
  • Cell Line, Tumor
  • Cholesterol / analogs & derivatives*
  • Cholesterol / analysis
  • Cholesterol / chemistry
  • Cholesterol / metabolism
  • Chromatography, High Pressure Liquid / methods*
  • Esters / analysis
  • Esters / chemistry
  • Esters / metabolism
  • Humans
  • Intracellular Space* / chemistry
  • Intracellular Space* / metabolism
  • Linear Models
  • Mass Spectrometry
  • Mice
  • Reproducibility of Results
  • Sensitivity and Specificity
  • Spectrometry, Fluorescence / methods*

Substances

  • 7-nitrobenz-2-oxa-1,3-diazol-4-ylcholesterol
  • Esters
  • Cholesterol
  • 4-Chloro-7-nitrobenzofurazan