Digitonin
(Synonyms: 洋地黄皂苷) 目录号 : GC32854
洋地黄皂苷是一种甾体皂苷，广泛用作温和的非离子洗涤剂。
Cas No.:11024-24-1
Sample solution is provided at 25 µL, 10mM.
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- Datasheet
| Cell experiment [1]: | |
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Cell lines |
Caco-2 and MCF-7 cells |
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Preparation Method |
The cells were incubated with 100 µl of medium containing different concentrations of digitonin and other secondary metabolites for 24 hours. |
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Reaction Conditions |
0-500µM for 24 hours. |
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Applications |
Digitonin showed the high exhibition to Caco-2, MCF-7 with IC50 of 15.72 ± 0.16 and 5.23 ± 0.61µM, respectively. |
| Animal experiment [2]: | |
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Animal models |
Inbred rats of both sexes of the Lister-Hooded (LH) strain |
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Preparation Method |
Digitonin was dissolved in dimethylsulfoxide (DMSO) and diluted with saline to yield a solution that contained 400 µM digitonin and 40 µM DMSO; 0.2 ml of the solution was infused into the hepatic artery. |
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Dosage form |
400 µM 0.2 ml of Digitonin solution, a catheter (PE 10, inner diameter 0.28 mm, outer diameter 0.61 mm) was inserted into the hepatic artery proper via the gastroduodenal artery |
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Applications |
After pretreatment with digitonin the platinum content in the tumour as measured at 1 h after CBDCA infusion was 66±19 ng/mg. This was more than 5 times higher than the values obtained after pretreatment with saline alone (12±4 ng/mg) or with DMSO-saline (10±2 ng/mg) |
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References: [1]: Eid S Y, El-Readi M Z, Wink M. Digitonin synergistically enhances the cytotoxicity of plant secondary metabolites in cancer cells[J]. Phytomedicine, 2012, 19(14): 1307-1314. |
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Digitonin is a steroidal saponin used extensively as a mild non-ionic detergent [1]. Digitonin finds application as a cholesterol precipitating agent [2]. Digitonin increases cell permeability by binding specifically to cholesterol in the cell membrane [4].
Digitonin had high exhibition against Caco-2, MCF-7 with IC50 of 15.72 ± 0.16 and 5.23 ± 0.61μM, respectively. Combinations of the panel of SM with a non-toxic concentration of digitonin (2 or 5 μM) generally enhanced the cytotoxicity in Caco-2, MCF-7 cells [3]. Pretreatment with digitonin increases the tumour uptake of carboplatin and potentiates the cytotoxic effect of carboplatin [4].
References:
[1]. Bridges C D. A method for preparing stable digitonin solutions for visual pigment extraction[J]. Vision Research, 1977, 17(2): 301-302.
[2]. Haust H L, Kuksis A, Beveridge J M R. Quantitative precipitation of various 3β-hydroxysterols with digitonin[J]. Canadian Journal of Biochemistry, 1966, 44(1): 119-128.
[3]. Eid S Y, El-Readi M Z, Wink M. Digitonin synergistically enhances the cytotoxicity of plant secondary metabolites in cancer cells[J]. Phytomedicine, 2012, 19(14): 1307-1314.
[4]. Lindnér P G, Heath D, Howell S B, et al. Digitonin enhances the efficacy of carboplatin in liver tumour after intra-arterial administration[J]. Cancer chemotherapy and pharmacology, 1997, 40(5): 444-448.
洋地黄皂苷是一种甾体皂苷,广泛用作温和的非离子洗涤剂[1]。洋地黄皂苷可用作胆固醇沉淀剂[2]。洋地黄皂苷通过特异性结合细胞膜中的胆固醇来增加细胞通透性[4]。
Digitonin 对 Caco-2、MCF-7 具有很强的抑制作用,IC50 分别为 15.72 ± 0.16 和 5.23 ± 0.61μM。 SM 组与无毒浓度的洋地黄皂苷（2 或 5 μM）的组合通常增强 Caco-2、MCF-7 细胞的细胞毒性[3]。毛地黄皂苷预处理可增加卡铂的肿瘤摄取并增强卡铂的细胞毒作用[4]。
| Cas No. | 11024-24-1 | SDF | |
| 别名 | 洋地黄皂苷 | ||
| Canonical SMILES | C[C@@]12[C@]([C@@H]3C)([H])[C@](O[C@]34CC[C@@H](C)CO4)([H])[C@@H](O)[C@@]1([H])[C@@](CC[C@]5([H])[C@@]6(C[C@@H](O)[C@H](O[C@]([C@@H]([C@@H](O)[C@H]7O[C@@](O[C@H](CO)[C@@H](O)[C@@H]8O[C@@](OC[C@@H](O)[C@@H]9O)([H])[C@@H]9O)([H])[C@@H]8O[C@@](O[C@H](CO)[C@H | ||
| 分子式 | C₅₆H₉₂O₂₉ | 分子量 | 1229.31 |
| 溶解度 | DMF: 30 mg/ml, DMSO: 30 mg/ml | 储存条件 | Store at 4°C, stored under nitrogen |
| 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 | 0.8135 mL | 4.0673 mL | 8.1346 mL |
| 5 mM | 0.1627 mL | 0.8135 mL | 1.6269 mL |
| 10 mM | 0.0813 mL | 0.4067 mL | 0.8135 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。
Digitonin does not flip across cholesterol-poor membranes
J Colloid Interface Sci 2017 Oct 15;504:283-293.PMID:28551523DOI:10.1016/j.jcis.2017.05.034.
Digitonin is commonly used to permeabilize cell membranes and solubilize membrane components. It interacts specifically with cholesterol in the membrane which leads to the formation of pores. Thus far, the mechanism by which Digitonin interacts with the membrane has only been described qualitatively. We investigated this interaction in model membranes that contain little or no cholesterol with a combination of isothermal titration calorimetry, dynamic light scattering, and zeta potential measurements. Digitonin partitions fully asymmetrically into large unilamellar vesicles of phosphocholine (PC) lipid at 20°C (remaining in the outer leaflet only), with a partition coefficient of 0.22±0.04mM-1 and ΔH of partitioning of 23.3±1.6kJmol-1. Beyond a Digitonin/lipid ratio of ∼0.1 in the outer leaflet, Digitonin micelles coexist with vesicles without solubilizing them-even at high Digitonin concentrations. This "staying out" of Digitonin was also observed with phosphoserine (PS), PC/PS, and PC/PS/cholesterol vesicles. The mechanism by which Digitonin perturbs and solubilizes the membrane is very different when the membrane contains little or no cholesterol as opposed to 20-30mol% cholesterol. The role of Digitonin should thus be carefully considered in the design of preparative protocols and experiments in studies of cellular processes and membrane proteins.
Radioimmunoassay of Digitonin
Biochim Biophys Acta 1982 Feb 8;685(1):39-43.PMID:7059589DOI:10.1016/0005-2736(82)90032-3.
We describe a radioimmunoassay for Digitonin which utilizes the ability of digotonin to compete with 125I-labeled digoxigenin for binding to anti-digoxin antiserum. As performed using the Gammaflo automated radioimmunoassay system and commercially available reagents, the assay can detect as little as 20 micrograms/ml (15 microM) Digitonin. The assay is insensitive to interference by cholesterol or other cell membrane constituents and is useable above and below the critical micelle concentration of Digitonin. It should be useful for the monitoring of Digitonin concentrations in solubilized biochemical preparations.
Digitonin concentration is determinant for mitochondrial supercomplexes analysis by BlueNative page
Biochim Biophys Acta Bioenerg 2021 Jan 1;1862(1):148332.PMID:33129827DOI:10.1016/j.bbabio.2020.148332.
The BlueNative page (BNGE) gel has been the reference technique for studying the electron transport chain organization since it was established 20 years ago. Although the migration of supercomplexes has been demonstrated being real, there are still several concerns about its ability to reveal genuine interactions between respiratory complexes. Moreover, the use of different solubilization conditions generates conflicting interpretations. Here, we thoroughly compare the impact of different Digitonin concentrations on the liquid dispersions' physical properties and correlate with the respiratory complexes' migration pattern and supercomplexes. Our results demonstrate that Digitonin concentration generates liquid dispersions with specific size and variability critical to distinguish between a real association of complexes from being trapped in the same micelle.
On the Interaction between Digitonin and Cholesterol in Langmuir Monolayers
Langmuir 2016 Sep 6;32(35):9064-73.PMID:27518122DOI:10.1021/acs.langmuir.6b01737.
In this article, we describe the effect of a highly hemolytic saponin, Digitonin, on model lipids cholesterol and dipalmitoylphosphatidylcholine (DPPC) using a combination of tensiometric (surface pressure and dilatational surface elasticity), spectroscopic (infrared reflection absorption spectroscopy, IRRAS), microscopic (fluorescence microscopy), and scattering techniques (neutron reflectivity, NR, and grazing incidence X-ray diffraction, GIXD). The monolayers of individual lipids and their 10:9 (mol/mol) mixture were exposed to an aqueous solution of Digitonin (10(-4) M) by subphase exchange using a setup developed recently in our laboratory. The results confirm that Digitonin can adsorb onto both bare and lipid-covered water-air interfaces. In the case of DPPC, a relatively weak interaction can be observed, but the presence of cholesterol drastically enhances the effect of Digitonin. The latter is shown to dissociate the weak cholesterol-DPPC complexes and to bind cholesterol in an additional layer attached to the original lipid monolayer.
Disordering Effects of Digitonin on Phospholipid Monolayers
Langmuir 2017 Apr 18;33(15):3871-3881.PMID:28333465DOI:10.1021/acs.langmuir.6b04613.
Digitonin, a steroidal saponin obtained from the foxglove plant (Digitalis purpurea), displays a wide spectrum of biological properties and is often used as a model in mechanistic investigations of the biological activity of saponins. In the present study, Langmuir monolayers of zwitterionic (DPPC, DMPE, POPC, POPE, DSPC, DSPE, and DPPE) and ionic (DPPS and DPPG) phospholipids were employed in order to better understand the effect of Digitonin on the lipid organization. For this purpose, a combination of surface pressure relaxation, infrared reflection absorption spectroscopy (IRRAS), and fluorescence microscopy measurements was used. The observed increase in surface pressure (Π) suggests that Digitonin can adsorb at the air/water interface, both bare and covered with the uncompressed phospholipid monolayers. However, the detailed analysis of IRRAS and fluorescence microscopy data shows that Digitonin interacts with the lipid monolayers in a very selective way, and both the headgroup and the lipid tails affect this interaction. Nevertheless, it should be noted that in no case did Digitonin cause any disruptive effects on the monolayers. The DPPE and DPPS monolayers get disordered by penetration with Digitonin, despite an increase in surface pressure, leading to an unprecedented LC-LE transition. Interestingly, saponin could be easily squeezed out of these monolayers by mechanical compression.