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| Predicate | Object |
|---|---|
| rdf:type | |
| lifeskim:mentions | |
| pubmed:issue |
9
|
| pubmed:dateCreated |
1985-10-17
|
| pubmed:abstractText |
Singlet oxygen adducts of various vitamin D derivatives, 6,19-dihydro-6,19-epidioxyvitamin D (vitamin D endoperoxides, 2 and 2'), were chemically synthesized, and their biological activity in inducing differentiation of a human myeloid leukemia cell line (HL-60 cells) was examined. The potency of the endoperoxides derived from vitamin D derivatives possessing the 1 alpha-hydroxyl group such as 1 alpha, 25-dihydroxyvitamin D3 endoperoxides (2b and 2b') was markedly (10(-2)) diminished relative to the respective parent vitamin D compounds. In contrast, 25-hydroxyvitamin D3 endoperoxides [25-(OH)D3 endoperoxides, 2a and 2a'] and their analogues fluorinated at the 24- or 26- and 27-positions were 2.5-10 times more potent than 25-hydroxyvitamin D3 (1a) in spite of the absence of the conjugated triene structure typical of vitamin D compounds. The potency of these vitamin D endoperoxides (2 and 2'), especially those lacking the 1 alpha-hydroxyl group, in inducing differentiation of HL-60 cells was not correlated with their activity in binding to the cytosol receptor for 1 alpha, 25-dihydroxyvitamin D3 (1b). The binding efficiency to the receptor was relatively lower than the differentiating activity. To examine the action of vitamin D endoperoxides, carbon analogues of 25-(OH)D3 endoperoxides, two C-6 epimers of 25-hydroxy-6,19-dihydro-6,19-ethanovitamin D3 (6 and 6'), were synthesized. The carbon analogues (6 and 6') had no potential to induce differentiation of HL-60 cells. These results suggest that vitamin D endoperoxides (2 and 2') express their biological activity probably after being converted to some other compounds.
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| pubmed:language |
eng
|
| pubmed:journal | |
| pubmed:citationSubset |
IM
|
| pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/Calcifediol,
http://linkedlifedata.com/resource/pubmed/chemical/Cholecalciferol,
http://linkedlifedata.com/resource/pubmed/chemical/Oxygen,
http://linkedlifedata.com/resource/pubmed/chemical/Receptors, Calcitriol,
http://linkedlifedata.com/resource/pubmed/chemical/Receptors, Steroid,
http://linkedlifedata.com/resource/pubmed/chemical/Singlet Oxygen
|
| pubmed:status |
MEDLINE
|
| pubmed:month |
Sep
|
| pubmed:issn |
0022-2623
|
| pubmed:author | |
| pubmed:issnType |
Print
|
| pubmed:volume |
28
|
| pubmed:owner |
NLM
|
| pubmed:authorsComplete |
N
|
| pubmed:pagination |
1148-53
|
| pubmed:dateRevised |
2008-11-21
|
| pubmed:meshHeading |
pubmed-meshheading:2993611-Binding, Competitive,
pubmed-meshheading:2993611-Calcifediol,
pubmed-meshheading:2993611-Cell Differentiation,
pubmed-meshheading:2993611-Cell Line,
pubmed-meshheading:2993611-Chemical Phenomena,
pubmed-meshheading:2993611-Chemistry,
pubmed-meshheading:2993611-Cholecalciferol,
pubmed-meshheading:2993611-Cytosol,
pubmed-meshheading:2993611-Dose-Response Relationship, Drug,
pubmed-meshheading:2993611-Humans,
pubmed-meshheading:2993611-Leukemia, Myeloid,
pubmed-meshheading:2993611-Oxidation-Reduction,
pubmed-meshheading:2993611-Oxygen,
pubmed-meshheading:2993611-Phagocytosis,
pubmed-meshheading:2993611-Receptors, Calcitriol,
pubmed-meshheading:2993611-Receptors, Steroid,
pubmed-meshheading:2993611-Singlet Oxygen,
pubmed-meshheading:2993611-Structure-Activity Relationship
|
| pubmed:year |
1985
|
| pubmed:articleTitle |
Syntheses and differentiating action of vitamin D endoperoxides. Singlet oxygen adducts of vitamin D derivatives in human myeloid leukemia cells (HL-60).
|
| pubmed:publicationType |
Journal Article,
Comparative Study
|