Total synthesis of 25-hydroxy-16,23E-diene vitamin D3 and 1 alpha,25-dihydroxy-16,23E-diene vitamin D3: separation of genomic and nongenomic vitamin D activities

Separation of genomic and nongenomic vitamin D activities was achieved by structural modification of 1,25-dihydroxy vitamin D3 by introduction of 16 and 23E double bonds. The modified compound 3, lacking a 1 alpha-hydroxy group, exhibits only nongenomic activity. Its 1 alpha-hydroxy relative 4 expre...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 1998-11, Vol.6 (11), p.2051-2059
Main Authors: Kabat, M M, Burger, W, Guggino, S, Hennessy, B, Iacobelli, J A, Takeuchi, K, Uskoković, M R
Format: Article
Language:English
Subjects:
Animals
Calcifediol - pharmacology
Calcitriol - pharmacology
Calcium - metabolism
Calcium Channels - drug effects
Calcium Channels - physiology
Cell Line
Cell Membrane - drug effects
Cell Membrane - physiology
Cells, Cultured
Cholecalciferol - analogs & derivatives
Cholecalciferol - chemical synthesis
Cholecalciferol - chemistry
Cholecalciferol - pharmacology
Indicators and Reagents
Intestines
Membrane Potentials - drug effects
Membrane Potentials - physiology
Mice
Models, Molecular
Molecular Conformation
Molecular Structure
Osteoblasts - drug effects
Osteoblasts - metabolism
Receptors, Calcitriol - metabolism
Signal Transduction
Space life sciences
Transcription, Genetic - drug effects
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Summary:Separation of genomic and nongenomic vitamin D activities was achieved by structural modification of 1,25-dihydroxy vitamin D3 by introduction of 16 and 23E double bonds. The modified compound 3, lacking a 1 alpha-hydroxy group, exhibits only nongenomic activity. Its 1 alpha-hydroxy relative 4 expresses fully both genomic and non-genomic activities. A total synthesis of analogues 3 and 4 is described.
ISSN:0968-0896
DOI:10.1016/S0968-0896(98)00164-3