The synthesis and bone resorbing activity of (25R)- and (25S)-26-hydroxycholecalciferol (26-OH-D3)
| Autor: | J Redel, F. Delbarre, C. Rebut-Bonneton |
|---|---|
| Rok vydání: | 1978 |
| Předmět: |
medicine.medical_specialty
Hydroxycholecalciferols Metabolite Calvaria Biochemistry Bone and Bones In vitro Bone resorption Mice Structure-Activity Relationship chemistry.chemical_compound Endocrinology medicine.anatomical_structure Isomerism chemistry In vivo Sephadex Internal medicine medicine Animals Calcium Epimer Bone Resorption Bone resorbing activity |
| Zdroj: | Journal of Steroid Biochemistry. 9:1179-1182 |
| ISSN: | 0022-4731 |
| DOI: | 10.1016/0022-4731(78)90009-2 |
| Popis: | The synthesis of C-25 epimers of 26-hydroxycholecalciferol (26-OH-D3) (III)—the so far unknown 25-deoxy analogue of the metabolite 25,26(OH)2D3—is described. (25R)- or (25S)-26-hydroxycholesterol 3,26-diacetate (I) was converted into the corresponding mixture of 5,7- and 4,6-diene, saponified and then directly irradiated with U.V. light. The obtained precholecalci ferol analog was isomerized thermally to III and separated from the 4,6-diene on Sephadex LH 20. Tested for bone resorption in organ cultures from mouse calvaria in vitro, (25R)-26-OH-D3 is less effective than 25,26(OH)2D3, whereas (25S)-26-OH-D3 is inactive. By the in vivo/in vitro method, (25R)and (25S)-26-OH-D3 are ineffective, while 25R,26- and 25S,26(OH)2D3 are moderately osteolytic. |
| Databáze: | OpenAIRE |
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