(24S)-24,25-Dihydroxyvitamin D3 - CAS 55700-58-8
Catalog number: 55700-58-8
Category: Inhibitor
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Molecular Formula:
C27H44O3
Molecular Weight:
416.64
COA:
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Targets:
VD/VDR
Description:
(24S)-24,25-Dihydroxycholecalciferol is an inactive form of vitamin D3 which undergoes various levels of hydroxylation to form active vitamin D3 analogs.
Purity:
>98%
MSDS:
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InChIKey:
FCKJYANJHNLEEP-WQUHCOROSA-N
InChI:
InChI=1S/C27H44O3/c1-18-8-12-22(28)17-21(18)11-10-20-7-6-16-27(5)23(13-14-24(20)27)19(2)9-15-25(29)26(3,4)30/h10-11,19,22-25,28-30H,1,6-9,12-17H2,2-5H3/b20-10+,21-11-/t19-,22+,23-,24+,25+,27-/m1/s1
Canonical SMILES:
CC(CCC(C(C)(C)O)O)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C
1.Putative basal lateral membrane receptors for 24,25-dihydroxyvitamin D(3) in carp and Atlantic cod enterocytes: characterization of binding and effects on intracellular calcium regulation.
Larsson D1, Nemere I, Sundell K. J Cell Biochem. 2001 Aug 1-9;83(2):171-86.
The vitamin D metabolite, 24R,25-dihydroxyvitamin D(3) (24R,25(OH)(2)D(3)), was tested for its ability to specifically bind to basal lateral membranes isolated from intestinal epithelium of Atlantic cod (a seawater fish), carp (a freshwater fish), and chicken. Specific saturable binding was demonstrated in membranes from all three species. Membranes from Atlantic cod, carp, and chicken revealed K(d)'s of 7.3 +/- 0.9, 12.5 +/- 0.9 and 7.8 +/- 0.1 nM, and a B(max) for each species estimated to 57.9 +/- 2.9, 195.1 +/- 8.4 and 175 +/- 0.8 fmol/mg protein, respectively. Scatchard analyses indicated a convex curvature and Hill analyses revealed apparent Hill coefficients of 1.84 +/- 0.28, 1.80 +/- 0.29, and 1.78 +/- 0.27 for Atlantic cod, carp and chicken, suggesting a positive cooperative binding in all three species. Basal lateral membranes from Atlantic cod and carp were used to further characterize the binding moiety. In competition studies, basal lateral membranes from Atlantic cod or carp did not discriminate between 24R,25(OH)(2)D(3) and the 24S,25(OH)(2)D(3) isomer, whereas, 1,25(OH)(2)D(3) and 25(OH)D(3), were less effective in competing with [(3)H]24R,25(OH)(2)D(3) for binding to basal lateral membranes in Atlantic cod and carp.
2.Update on biological actions of 1alpha,25(OH)2-vitamin D3 (rapid effects) and 24R,25(OH)2-vitamin D3.
Norman AW1, Okamura WH, Bishop JE, Henry HL. Mol Cell Endocrinol. 2002 Nov 29;197(1-2):1-13.
All biologic responses to vitamin D are now known to arise as a consequence of the metabolism of this seco-steroid into its two principal biologically active metabolites 1alpha,25(OH)(2)-vitamin D(3) (1ALPHA;,25(OH)(2)D(3)) and 24R,25(OH)(2)-vitamin D(3) (24R,25(OH)(2)D(3)). 1alpha,25(OH)(2)D(3) is the dominant metabolite and produces a wide array of biological responses via interacting both with the classical vitamin D nuclear receptor (VDR(nuc)) that regulates gene transcription in over 30 target organs and with a putative cell membrane receptor (VDR(mem1,25)) that mediates rapid (within seconds to minutes) biological responses. Ligand occupancy of VDR(mem1,25) is linked to signal transduction systems that can mediate the opening of Ca(2+) and chloride voltage gated channels as well as activation of MAP-kinase. MAP-kinase activation in some cells containing VDR(mem1,25)+VDR(nuc) then results in "cross-talk" from VDR(mem1,25) to VDR(nuc) which modulates transactivation of 1alpha,25(OH)(2)D(3) responsive gene promoters.
3.24R,25-dihydroxyvitamin D3 increases cyclic GMP contents, leading to an enhancement of osteocalcin synthesis by 1,25-dihydroxyvitamin D3 in cultured human osteoblastic cells.
Yamamoto T1, Ozono K, Shima M, Yamaoka K, Okada S. Exp Cell Res. 1998 Oct 10;244(1):71-6.
The effect of the physiological vitamin D metabolite 24R, 25-dihydroxyvitamin D3 [24R,25(OH)2D3] on human osteoblastic cells was assessed. Physiological concentrations (10(-9)-10(-8) M) of 24R, 25(OH)2D3 significantly increased the cyclic guanosine 5'-monophosphate (cGMP) content in the human osteoblastic cells by approximately 200% in 5 to 15 min. In contrast, 24S, 25-dihydroxyvitamin D3 had only a weak effect on the cGMP content, and 1,25-dihydroxyvitamin D3 [1,25(OH)2D3] did not affect the content. The production of osteocalcin was not induced by 10(-9)-10(-8) M of 24R,25(OH)2D3 in the absence of 1,25(OH)2D3. However, the same concentration of 24R,25(OH)2D3 showed stimulatory effects on osteocalcin synthesis in the presence of 10(-9) M 1, 25(OH)2D3. Rp-8Br-cyclic GMP, a specific inhibitor of cyclic GMP-dependent protein kinase, significantly inhibited the cooperative effect of 24R,25(OH)2D3 with 1,25(OH)2D3 on the osteocalcin synthesis, although Rp-8Br-cyclic AMP, a specific inhibitor of cyclic AMP-dependent protein kinase, did not affect the cooperative effect.
4.Studies on 24R,25-dihydroxyvitamin D3: evidence for a nonnuclear membrane receptor in the chick tibial fracture-healing callus.
Kato A1, Seo EG, Einhorn TA, Bishop JE, Norman AW. Bone. 1998 Aug;23(2):141-6.
The effect(s) of 24R,25-dihydroxyvitamin D3 [24R,25(OH)2D3] on fracture healing was studied in a vitamin D-depleted chick model. 24R,25(OH)2D3, together with another hormonally active vitamin D metabolite, 1alpha,25-dihydroxyvitamin D3 [1alpha,25(OH)2D3], improved bone mechanical strength parameters (torsional strength, angular deformation, and stiffness) and the ash content. The synthetic epimer 24S,25-dihydroxyvitamin D3 [24S,25(OH)2D3] was not as potent as the natural 24R,25(OH)2D3. In light of the ability of the fracture-healing callus to discriminate between 24R,25(OH)2D3 and 24S,25(OH)2D3, a search was initiated in fracture-healing callus tissue for the presence of a specific 24R,25(OH)2D3 receptor. No evidence was obtained for a classical nuclear/cytosol receptor for 24R,25(OH)2D3 in the fracture-healing callus. A specific receptor/binding protein for 24R,25(OH)2D3 was found in the callus membrane fraction, which showed different ligand binding affinities [KD = 18.
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CAS 55700-58-8 (24S)-24,25-Dihydroxyvitamin D3

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