1alpha, 25-Dihydroxy VD2-D6CAS# 216244-04-1 |
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Quality Control & MSDS
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| Cas No. | 216244-04-1 | SDF | Download SDF |
| PubChem ID | 66577026 | Appearance | Powder |
| Formula | C28H44O3 | M.Wt | 428.6 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | DMSO | ||
| Chemical Name | (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(E,2R,5S)-7,7,7-trideuterio-6-hydroxy-5-methyl-6-(trideuteriomethyl)hept-3-en-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol | ||
| SMILES | CC(C=CC(C)C(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C | ||
| Standard InChIKey | ZGLHBRQAEXKACO-NHXRPVGSSA-N | ||
| Standard InChI | InChI=1S/C28H44O3/c1-18(9-10-19(2)27(4,5)31)24-13-14-25-21(8-7-15-28(24,25)6)11-12-22-16-23(29)17-26(30)20(22)3/h9-12,18-19,23-26,29-31H,3,7-8,13-17H2,1-2,4-6H3/b10-9+,21-11+,22-12-/t18-,19+,23-,24-,25+,26+,28-/m1/s1/i4D3,5D3 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 1alpha, 25-Dihydroxy VD2-D6 is a deuterated form of vitamin D. |
1alpha, 25-Dihydroxy VD2-D6 Dilution Calculator
1alpha, 25-Dihydroxy VD2-D6 Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.3332 mL | 11.6659 mL | 23.3318 mL | 46.6636 mL | 58.3294 mL |
| 5 mM | 0.4666 mL | 2.3332 mL | 4.6664 mL | 9.3327 mL | 11.6659 mL |
| 10 mM | 0.2333 mL | 1.1666 mL | 2.3332 mL | 4.6664 mL | 5.8329 mL |
| 50 mM | 0.0467 mL | 0.2333 mL | 0.4666 mL | 0.9333 mL | 1.1666 mL |
| 100 mM | 0.0233 mL | 0.1167 mL | 0.2333 mL | 0.4666 mL | 0.5833 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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1alpha, 25-Dihydroxy VD2-D6
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Metabolism of selective 20-epi-vitamin D3 analogs in rat osteosarcoma UMR-106 cells: Isolation and identification of four novel C-1 fatty acid esters of 1alpha,25-dihydroxy-16-ene-20-epi-vitamin D3.[Pubmed:28089927]
Steroids. 2017 Mar;119:18-30.
Analogs of 1alpha,25-dihydroxyvitamin D3 (S1) with 20-epi modification (20-epi analogs) possess unique biological properties. We previously reported that 1alpha,25-dihydroxy-20-epi-vitamin D3 (S2), the basic 20-epi analog is metabolized into less polar metabolites (LPMs) in rat osteosarcoma cells (UMR-106) but not in a perfused rat kidney. Furthermore, we also noted that only selective 20-epi analogs are metabolized into LPMs. For example, 1alpha,25-dihydroxy-16-ene-20-epi-vitamin D3 (S4), but not 1alpha,25-dihydroxy-16-ene-23-yne-20-epi-vitamin D3 (S5) is metabolized into LPMs. In spite of these novel findings, the unequivocal identification of LPMs has not been achieved to date. We report here on a thorough investigation of the metabolism of S4 in UMR-106 cells and isolated two major LPMs produced directly from the substrate S4 itself and two minor LPMs produced from 3-epi-S4, a metabolite of S4 produced through C-3 epimerization pathway. Using GC/MS, ESI-MS and (1)H NMR analysis, we identified all the four LPMs of S4 as 25-hydroxy-16-ene-20-epi-vitamin D3-1-stearate and 25-hydroxy-16-ene-20-epi-vitamin D3-1-oleate and their respective C-3 epimers. We report here for the first time the elucidation of a novel pathway of metabolism in UMR-106 cells in which both 1alpha,25(OH)2-16-ene-20-epi-D3 and 1alpha,25(OH)2-16-ene-20-epi-3-epi-D3 undergo C-1 esterification into stearic and oleic acid esters.
A new suprasterol by photochemical reaction of 1alpha,25-dihydroxy-9-methylene-19-norvitamin D3.[Pubmed:26693597]
Org Biomol Chem. 2016 Feb 7;14(5):1646-52.
The UV-induced photochemical reaction of 1alpha,25-dihydroxy-9-methylene-19-norvitamin D3 has been investigated. The pentacyclic structure of the isolated product has been unequivocally established by X-ray crystallographic analysis. The possible reaction paths of the examined photochemical transformation are discussed. Biological in vivo and in vitro tests proved that the photoproduct is devoid of calcemic activity.
Synthesis of 2alpha- and 2beta-(3-hydroxypropyl)- 7,8-cis-14-epi-1alpha,25-dihydroxy-19-norvitamin D3 and their biological activity.[Pubmed:27629592]
J Steroid Biochem Mol Biol. 2017 Oct;173:79-82.
According to the binding mode of 14-epi-1alpha,25-dihydroxy-19-nortachysterol in the ligand binding domain of human vitamin D receptor (hVDR), i.e., 5,6- and 7,8-s-trans configuration that was shown by X-ray co-crystallographic analysis, 7,8-cis-locked 1alpha,25(OH)2D3 analogs were synthesized. In this paper, the synthesis and biological activity of 2alpha- and 2beta-(3-hydroxypropyl)-7,8-cis-14-epi-1alpha,25-dihydroxy-19-norvitamin D3 are reported. The A-ring and CD-ring precursors for the Julia-Kociensky coupling reaction to create a diene system of the target molecules were prepared using our original methods. hVDR binding affinity and osteocalcin promoter transactivation activity of the new 7,8-cis-14-epi-vitamin D3 analogs were evaluated. Interestingly, the 2beta-substituted 7,8-cis-analog was a better binder for hVDR than the 2alpha-isomeric counterpart.
Synthesis, metabolism, and biological activity of 2-[3-(tetrazolyl)propyl]-1alpha,25-dihydroxy-19-norvitamin D3.[Pubmed:26232635]
J Steroid Biochem Mol Biol. 2016 Nov;164:40-44.
Recently, we found that 2alpha-[2-(tetrazol-2-yl)ethyl]-1alpha,25-dihydroxyvitamin D3 showed higher osteocalcin promoter transactivation activity in human osteosarcoma (HOS) cells and a greater therapeutic effect in ovariectomized (OVX) rats in vivo than those of active vitamin D3, 1alpha,25(OH)2D3. We were interested in introducing a heterocyclic ring to the C2 position of the seco-steroidal structure via an alkyl linker, and four novel C2-(3-tetrazolylpropyl) substituted 1alpha,25-dihydroxy-19-norvitamin D3 analogs, 2alpha-[3-(tetrazol-1-yl)propyl]-, 2beta-[3-(tetrazol-1-yl)propyl]-, 2alpha-[3-(tetrazol-2-yl)propyl]-, and 2beta-[3-(tetrazol-2-yl)propyl]-19-nor-1alpha,25(OH)2D3 were synthesized. Among them, 2alpha-[3-(tetrazol-1-yl)propyl]-19-nor-1alpha,25(OH)2D3 showed weak binding affinity for human vitamin D receptor (hVDR) (2.6% of 1alpha,25(OH)2D3 and ca. 15% of 19-nor-1alpha,25(OH)2D3) and weak VDR transactivation activity in HOS cells (EC50 7.3nM, when 1alpha,25(OH)2D30.23nM). Although the other three compounds could not act as VDR binders by evaluation of the competition assays, 2alpha-[3-(tetrazol-2-yl)propyl]-19-nor-1alpha,25(OH)2D3 showed weak transactivation activity (EC50 12.5nM). Metabolic stability of the 2alpha-substituted compounds 2alpha-[3-(tetrazol-1-yl)propyl]- and 2alpha-[3-(tetrazol-2-yl)propyl]-19-nor-1alpha,25(OH)2D3 was higher than that of the 2beta-substituted counterparts 2beta-[3-(tetrazol-1-yl)propyl]- and 2beta-[3-(tetrazol-2-yl)propyl]-19-nor-1alpha,25(OH)2D3 against human CYP24A1. Introduction of a tetrazole ring to the C2-position of the 19-norvitamin D3 skeleton with the propyl linker led to weak VDR agonistic activity with stability against CYP24A1 metabolism.
