Bone resorptive activity of side-chain fluoro derivatives of 25-hydroxy- and 1α,25-dihydroxyvitamin D3 in culture

Paula H Stern, Y. Tanaka, H. F. DeLuca, N. Ikekawa, Y. Kobayashi

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

Three side-chain fluorinated analogues of vitamin D3 were tested for their bone-resorbing activity on fetal rat forelimb bones in vitro. Two fluoro derivatives of 25-hydroxyvitamin D3 (25-OH-D3), 24,24-difluoro-25-hydroxyvitamin D3 and 25-hydroxy-26,26,26,27,27,27-hexafluorovitamin D3, were compared with 25-OH-D3. The difluoro compound was approximately 7 times more potent than 25-OH-D3, and the hexafluoro analogue was approximately 40 times more potent than 25-OH-D3 in this system. In contrast, the 24,24-difluoro analogue of 1α,25-dihydroxyvitamin D3 (1α,25-(OH)2D3) was slightly less potent than 1α,25-(OH)2D3. The results indicate that the presence of fluoride groups on carbon atoms immediately adjacent to the 25-hydroxyl group enhances the in vitro bone-resorbing effects of 25-hydroxyvitamin D3. On the other hand, fluorination of the 1α-hydroxylated compound on position 24 actually diminished rather than increased bone-resorptive activity.

Original languageEnglish (US)
Pages (from-to)460-462
Number of pages3
JournalMolecular Pharmacology
Volume20
Issue number3
StatePublished - Dec 1 1981

ASJC Scopus subject areas

  • Molecular Medicine
  • Pharmacology

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