Increased biological potency of hexafluorinated analogs of 1,25-dihydroxyvitamin D3 on bovine parathyroid cells

J Steroid Biochem Mol Biol. 1999 Sep-Oct;70(4-6):243-8. doi: 10.1016/s0960-0760(99)00112-0.

Abstract

1,25-dihydroxyvitamin D3 (1,25-(OH)2D3) is known to be involved in regulating the proliferation of parathyroid cells and PTH synthesis through reactions involving its nuclear receptor. We evaluated the effects of 1,25-(OH)2D3 and its hexafluorinated analog, 26,26,26,27,27,27-hexafluoro-1,25-dihydroxyvitamin D3 (26,27-F6-1,25-(OH)2D3), on parathyroid cells. The 1,25-(OH)2D3 and 26,27-F6-1,25-(OH)2D3 each inhibited [3H]thymidine incorporation and ornithine decarboxylase (ODC) activity, which is important in cell proliferation, in primary cultured bovine parathyroid cells. The inhibitory effect of 26,27-F6-1,25-(OH)2D3 on PTH secretion from parathyroid cells was significantly more potent than that of 1,25-(OH)2D3 between 10(-11) M and 10(-8) M. Study of 26,27-F6-1,25-(OH)2D3 metabolism in parathyroid cells in vitro elucidated its slower degradation than that of 1,25-(OH)2D3. After 48 h of incubation with [1beta-3H]26,27-F6-1,25-(OH)2D3, two HPLC peaks, one for [1beta-3H]26,27-F6-1,25-(OH)2D3, and a second larger peak for [1beta-3H]26,27-F6-1,23(S),25-(OH)3D3, were detected. No metabolites were detected after the same period of incubation with 1,25-(OH)2[26,27-3H]D3. We observed that 26,27-F6-1,23(S),25-(OH)3D3 was as potent as 1,25-(OH)2D3 in inhibiting the proliferation of parathyroid cells. Data suggest that the greater biological activity of 26,27-F6-1,25-(OH)2D3 is explained by its slower metabolisms and by the retention of the biological potency of 26,27-F6-1,25-(OH)2D3 even after 23(S)-hydroxylation.

MeSH terms

  • Animals
  • Biotransformation
  • Calcitriol / analogs & derivatives*
  • Calcitriol / pharmacokinetics
  • Calcitriol / pharmacology*
  • Cattle
  • Cell Division / drug effects
  • Cells, Cultured
  • Chromatography, High Pressure Liquid
  • DNA / biosynthesis
  • Kinetics
  • Ornithine Decarboxylase / metabolism
  • Parathyroid Glands / cytology
  • Parathyroid Glands / drug effects*
  • Parathyroid Glands / physiology
  • Parathyroid Hormone / metabolism*
  • Thymidine / metabolism

Substances

  • Parathyroid Hormone
  • DNA
  • Ornithine Decarboxylase
  • Calcitriol
  • 26,26,26,27,27,27-hexafluoro-1,25-dihydroxyvitamin D3
  • Thymidine