delta 5,7,9(11)-Cholestatrien-3 beta-ol: a fluorescent cholesterol analogue. Academic Article uri icon

abstract

  • Structural analysis, a purification scheme and stability information on a fluorescent cholesterol analogue, which has been used as a probe in several model and biological systems, are presented. The proposed structure for the fluorophore, cholestatrien-3 beta-ol, closely resembles that of cholesterol. However, problems of low yield during synthesis and rapid decomposition have impeded its use. This study concerns the synthesis and purification of cholestatrien-3 beta-ol by reverse phase high performance liquid chromatography (HPLC). Unlike cholestatrien-3 beta-ol recrystallized from solvents, the fluorescent sterol purified by HPLC was stable over several months at -70 degrees C either as a white, crystalline powder or in ethanolic solution. In model membranes the fluorescence of cholestatrien-3 beta-ol was stable to ultraviolet (UV) light. A simple spectroscopic assay for purity is presented. Included are detailed absorbance, fluorescence, mass, 1H-NMR, and 13C-NMR spectral analyses. The data confirm the structure of cholestatrien-3 beta-ol proposed, but not proven, over 50 years ago, delta 5,7,9(11)-cholestatrien-3 beta-ol.

published proceedings

  • Chem Phys Lipids

author list (cited authors)

  • Fischer, R. T., Stephenson, F. A., Shafiee, A., & Schroeder, F.

citation count

  • 87

complete list of authors

  • Fischer, RT||Stephenson, FA||Shafiee, A||Schroeder, F

publication date

  • November 1984