Digoxigenin Bisdigitoxoside
(Synonyms: Bisdigoxigenin) 目录号 : GC49842
A Na+/K+-ATPase inhibitor
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Digoxigenin bisdigitoxoside is a Na+/K+-ATPase inhibitor and an active cardiac glycoside metabolite of digoxin .1,2 It is formed from digoxin by the cytochrome P450 (CYP) isoform CYP3A.3 Digoxigenin bisdigitoxoside inhibits the Na+/K+-ATPase isoforms α1β1 and α2β1 with Ki values of 196 and 74 nM, respectively.
1.Katz, A., Tal, D.M., Heller, D., et al.Digoxin derivatives with enhanced selectivity for the α2 isoform of Na,K-ATPase: Effects on intraocular pressure in rabbitsJ. Biol. Chem.289(30)21153-21162(2014) 2.Abshagen, U., and Rietbrock, N.Metabolism of digoxigenin, digoxigeninmonodigitoxoside and digoxigeninbisdigitoxoside in ratsNaunyn Schmiedebergs Arch Pharmacol.276(2)157-166(1973) 3.Salphati, L., and Benet, L.Z.Metabolism of digoxin and digoxigenin digitoxosides in rat liver microsomes: Involvement of cytochrome P4503AXenobiotica29(2)171-185(1999)
| Cas No. | 5/2/5297 | SDF | Download SDF |
| 别名 | Bisdigoxigenin | ||
| Canonical SMILES | O[C@@]12[C@@]([C@](C3=CC(OC3)=O)([H])CC1)([C@@H](C[C@@]4([H])[C@@]2([H])CC[C@@]5([H])[C@@]4(CC[C@@H](C5)O[C@H]6C[C@@H]([C@@H]([C@H](O6)C)O[C@H]7C[C@@H]([C@@H]([C@H](O7)C)O)O)O)C)O)C | ||
| 分子式 | C35H54O11 | 分子量 | 650.8 |
| 溶解度 | DMSO: slightly soluble,Methanol: slightly soluble w/ sonication | 储存条件 | -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.5366 mL | 7.6829 mL | 15.3657 mL |
| 5 mM | 0.3073 mL | 1.5366 mL | 3.0731 mL |
| 10 mM | 0.1537 mL | 0.7683 mL | 1.5366 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Synthesis of C3-Neoglycosides of digoxigenin and their anticancer activities
Eur J Med Chem 2018 Feb 10;145:252-262.PMID:29329000DOI:10.1016/j.ejmech.2017.12.086.
Cardiac glycosides exhibit significant anticancer effects and the glycosyl substitution at C3 position of digoxigenin is pivotal for their biological activity. In order to study the structure-activity relationship (SAR) of cardiac glycosides toward cancers and explore more potent anticancer agents, a series of C3-O-neoglycosides and C3-MeON-neoglycosides of digoxigenin were synthesized by the Koenigs-Knorr and neoglycosylation method, respectively. In addition, Digoxigenin Bisdigitoxoside and monodigitoxoside were prepared from digoxin by sodium periodate (NaIO4) oxidation and 6-aminocaproic acid hydrolysis. The SAR analysis revealed that C3-O-neoglycosides of digoxigenin exhibited stronger cytotoxicity and induction of Nur77 expression of tumor cells than C3-MeON-neoglycosides. Also, 3β-O-glycosides exhibited stronger anticancer effects than 3α-O-glycosides. Among them, 3β-O-(β-l-fucopyranosyl)-digoxigenin (3i) showed the highest activity on induction of Nur77 expression and translocation from the nucleus to cytoplasm, leading to cancer cell apoptosis.
Metabolism and rate of elimination of Digoxigenin Bisdigitoxoside in dogs before and during chronic azotemia
J Pharmacol Exp Ther 1980 Mar;212(3):448-51.PMID:7359346doi
The purpose of this study was to evaluate the metabolism and rate of elimination of Digoxigenin Bisdigitoxoside (bis) before and during chronic azotemia in dogs. Bis was eliminated primarily by nonrenal mechanisms. The half-life of bis was 18.5 hr, compared to 31.6 hr for digoxin, and was not significantly increased in azotemic dogs. The oral bioavailability of bis in azotemic dogs relative to an intravenous dose was approximately 46%.
High-performance thin-layer chromatographic determination of digoxin and related compounds, Digoxigenin Bisdigitoxoside and gitoxin, in digoxin drug substance and tablets
J Chromatogr A 1994 Jan 21;659(1):177-83.PMID:8118558DOI:10.1016/0021-9673(94)85019-4.
A high-performance thin-layer chromatographic (HPTLC) method for the determination of digoxin and its related compounds Digoxigenin Bisdigitoxoside (DBD) and gitoxin in digoxin drug substance and tablets was developed. Separation of the three compounds was accomplished on a C18 wettable reversed-phase plate using water-methanol-ethyl acetate (50:48:2, v/v/v) as the mobile phase. The analytes were determined by densitometry using absorbance for digoxin and fluorescence for the two related compounds. All peaks were quantified by peak-height analysis. Linear regression analysis of the data was performed for all three compounds. The calibration range for digoxin was set at 320-480 ng per 5-mm band, equivalent to 80-120% (w/w) of a 400-ng band load, that for DBD was set at 4-12 ng per 5-mm band, equivalent to 1-3% (w/w) of the digoxin load, and that for gitoxin was set at 0.4-1.6 ng per 5-mm band, equivalent to 0.1-0.4% (w/w) of the digoxin load. The limit of quantification (LOQ) for digoxin was 64 ng per 5-mm band with a limit of detection (LOD) of 8 ng per 5-mm band. The LOQs for both DBD and gitoxin were 0.12 ng per 5-mm band with LODs of 0.4 ng per 5-mm band. The linearity range for the digoxin peak height in the absorbance mode was 0-5000 ng per 5-mm band. The linearity range for DBD and gitoxin peak heights in the fluorescence mode was 0-2000 ng per 5-mm band.
Structural studies on the biosides of Digitalis lanata: bisdigitoxosides of digitoxigenin, gitoxigenin and digoxigenin
Acta Crystallogr B 1989 Jun 1;45 ( Pt 3):306-12.PMID:2619961DOI:10.1107/s0108768189001734.
The crystal structures and conformations of bisdigitoxosides of digitoxigenin (I), gitoxigenin (II) and digoxigenin (III and IV) have been determined using single-crystal X-ray crystallographic techniques. Crystals of (I), (II) and (IV) were grown from ethyl acetate solutions of the glycosides while (III) was grown from a solution of the digitoxoside in ethanol. As in other cardiac glycosides the ring junctions A-B and C-D are cis. The D ring in these structures shows different conformations while the A, B and C rings remain conformationally similar. Although digitoxigenin bisdigitoxoside and gitoxigenin bisdigitoxoside differ from each other in the absence and presence of a hydroxyl group at C(16) of the D ring, these two biosides crystallize in the space group P2(1)2(1)2 [corrected] and are isomorphous. The presence of the hydroxyl group at C(16) does not affect the orientation of the lactone ring and the conformation of the molecule. Digoxigenin Bisdigitoxoside crystallizes in two different crystal systems with four molecules of water in the orthorhombic form and one molecule of ethyl acetate in the triclinic form. In both forms the hydroxyl at C(3') of the first sugar forms a hydrogen bond with the ring oxygen of the second sugar. This has also been observed in the trioside digoxin. The torsion angle C(13)-C(17)-C(20)-C(22) in the two forms differs by 7 degrees.(ABSTRACT TRUNCATED AT 250 WORDS)
Digoxin degradation in acidic dissolution medium
J Pharm Sci 1980 Apr;69(4):410-3.PMID:7373535DOI:10.1002/jps.2600690412.
The release of digoxin and its simultaneous conversion to Digoxigenin Bisdigitoxoside, digoxigenin monodigitoxoside, and digoxigenin in a USP dissolution test medium were followed by high-pressure liquid chromatography. Two products, Tablets A and B, were manufactured by solvent deposition and simple blending methods, respectively. Tablet A released digoxin faster than Tablet B in distilled water and in artificial intestinal juice, and no decomposition was observed. In the USP dissolution test medium, the rate of hydrolysis to Digoxigenin Bisdigitoxoside was almost equal to that of hydrolysis to digoxigenin monodigitoxoside, and a comparatively large formation rate of digoxigenin was observed. Concentrations of digoxin and its decomposition products were described by differential equations that included dissolution rates of digoxin (rapidly dissolving digoxin and digoxin crystals) and an apparent hydrolysis rate. In the earlier stage of dissolution, hydrolysis was rate determining; in the later stage, dissolution became the rate-determining step for overall digoxin degradation. To suppress digoxin hydrolysis in the USP dissolution test medium, a developmental formulation study was performed. The incorporation of magnesium oxide and magnesium hydroxide-aluminum hydroxide in the tablet formulations inhibited digoxin hydrolysis by 15.3 and 14.5%, respectively, after dissolution for 30 min without serious delay of drug release.