Impurity B of Calcitriol - CAS 66791-71-7
Catalog number: 66791-71-7
Category: Inhibitor
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Molecular Formula:
C27H44O3
Molecular Weight:
416.64
COA:
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Targets:
VD/VDR
Description:
Impurity B of Calcitriol is the hormonally active form of vitamin D, and Calcitriol is the active metabolite of vitamin D3 that activates the vitamin D receptor (VDR), which inhibits in vivo and in vitro cell proliferation in a wide range of cells including breast, prostate, colon, skin and brain carcinomas and myeloid leukemia cells.
Purity:
>98%
Synonyms:
1β,25-Dihydroxyvitamin-D3; 1-Epicalcitriol
MSDS:
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InChIKey:
GMRQFYUYWCNGIN-PEJFXWBPSA-N
InChI:
InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25-,27-/m1/s1
Canonical SMILES:
CC(CCCC(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C
1.Synthesis and biological activities of 2 alpha-chloro-1-epicalcitriol and 1-epicalcitriol.
Schönecker B;Reichenbächer M;Gliesing S;Gonschior M;Griebenow S;Scheddin D;Mayer H Steroids. 1998 Jan;63(1):28-36.
Anomalous diequatorial epoxide ring opening of 1 beta, 2 beta-oxido-cholesta-5,7-diene-3 beta, 25-diol 1 produces the 1 beta-hydroxy-2 alpha-chloro-provitamin 2 and its corresponding 1 beta-hydroxy-provitamin 3. The provitamins 2 and 3 are transformed by irradiation and thermal isomerization to 2 alpha-chloro-1-epicalcitriol NS3 (4) and 1-epicalcitriol NS8 (5), respectively. These two A-ring derivatives were tested for their in vitro biological activity in the mesenchymal, murine cell line C3H10T1/2, and their effects were compared with those of the native vitamin D3 derivatives 25(OH)D3 and 1.25(OH)2D3. NS3 and NS8 showed marked differences in their affinity for the vitamin D binding protein (DBP) and in their ability to inhibit cell proliferation. NS8 has the ability to bind to a high-affinity DBP-binding site for which 25(OH)D3 has none affinity. The 2 alpha-chloro-substitution (NS3) prevents binding to the postulated noncompetitive, NS8-specific DBP-binding site and diminishes the affinity to the vitamin D receptor (VDR) and therefore diminishing NS3's biological abilities. The elucidation of the structure-function relationships at the DBP-binding-sites could have major impact on the development of new vitamin D3 derivatives with extended serum half-life.
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CAS 66791-71-7 Impurity B of Calcitriol

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