Dehydroergosterol
(Synonyms: DHE, 9,11-dehydro Ergosterol) 目录号 : GC43404A fluorescent cholesterol analog
Cas No.:516-85-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >96.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Dehydroergosterol is a naturally occurring, fluorescent analog of cholesterol (ex/em = 324/375 nm) that mimics the properties of cholesterol in cell membranes.[1] It is readily bound by cholesterol-binding proteins and has been used for real-time probing of the sterol environment and to elucidate intracellular sterol trafficking in living organisms.[1]
Reference:
[1]. McIntosh, A.L., Atshaves, B.P., Huang, H., et al. Fluorescence techniques using dehydroergosterol to study cholesterol trafficking. Lipids 43(12), 1185-1208 (2008).
| Cas No. | 516-85-8 | SDF | |
| 别名 | DHE, 9,11-dehydro Ergosterol | ||
| 化学名 | ergosta-5,7,9(11),22E-tetraen-3β-ol | ||
| Canonical SMILES | CC(C)[C@@H](C)/C=C/[C@@H](C)[C@@]1([H])CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)C3=CC[C@@]21C | ||
| 分子式 | C28H42O | 分子量 | 394.6 |
| 溶解度 | 20mg/mL in ethanol, 0.1mg/mL in DMSO, 2mg/mL in DMF | 储存条件 | Store at -20°C,protect from light |
| 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 | 2.5342 mL | 12.6711 mL | 25.3421 mL |
| 5 mM | 0.5068 mL | 2.5342 mL | 5.0684 mL |
| 10 mM | 0.2534 mL | 1.2671 mL | 2.5342 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。
Dehydroergosterol as an analogue for cholesterol: why it mimics cholesterol so well-or does it?
J Phys Chem B 2014 Jul 3;118(26):7345-57.PMID:24893063DOI:10.1021/jp406883k.
Although Dehydroergosterol (DHE) is one of the most commonly used cholesterol (CHOL) reporters, it has remained unclear why it performs well compared with most other CHOL analogues and what its possible limitations are. We present a comprehensive study of the properties of DHE using a combination of time-resolved fluorescence spectroscopy, quantum-mechanical electronic structure computations, and classical atomistic molecular dynamics simulations. We first establish that DHE mimics CHOL behavior, as previous studies have suggested, and then move on to elucidate and discuss the particular properties that render DHE so superior. We found that the main reason why DHE mimics CHOL so well is due to its ability to stand upright in a membrane in a manner that is almost identical to that of CHOL. The minor difference in how DHE and CHOL tilt with respect to membrane normal has only faint effects on structural membrane properties, and even the lateral pressure profiles of model membranes with CHOL or DHE are almost identical. These results suggest that the mechanical/elastic effects of DHE on the function of mechanically sensitive membrane proteins are not substantially different from those of CHOL. Our study highlights similar dynamical behavior of CHOL and DHE, which implies that DHE can mimic CHOL in processes with free energies close to the thermal energy.
Fluorescence techniques using Dehydroergosterol to study cholesterol trafficking
Lipids 2008 Dec;43(12):1185-208.PMID:18536950DOI:10.1007/s11745-008-3194-1.
Cholesterol itself has very few structural/chemical features suitable for real-time imaging in living cells. Thus, the advent of Dehydroergosterol [ergosta-5,7,9(11),22-tetraen-3beta-ol, DHE] the fluorescent sterol most structurally and functionally similar to cholesterol to date, has proven to be a major asset for real-time probing/elucidating the sterol environment and intracellular sterol trafficking in living organisms. DHE is a naturally occurring, fluorescent sterol analog that faithfully mimics many of the properties of cholesterol. Because these properties are very sensitive to sterol structure and degradation, such studies require the use of extremely pure (>98%) quantities of fluorescent sterol. DHE is readily bound by cholesterol-binding proteins, is incorporated into lipoproteins (from the diet of animals or by exchange in vitro), and for real-time imaging studies is easily incorporated into cultured cells where it co-distributes with endogenous sterol. Incorporation from an ethanolic stock solution to cell culture media is effective, but this process forms an aqueous dispersion of DHE crystals which can result in endocytic cellular uptake and distribution into lysosomes which is problematic in imaging DHE at the plasma membrane of living cells. In contrast, monomeric DHE can be incorporated from unilamellar vesicles by exchange/fusion with the plasma membrane or from DHE-methyl-beta-cyclodextrin (DHE-MbetaCD) complexes by exchange with the plasma membrane. Both of the latter techniques can deliver large quantities of monomeric DHE with significant distribution into the plasma membrane. The properties and behavior of DHE in protein-binding, lipoproteins, model membranes, biological membranes, lipid rafts/caveolae, and real-time imaging in living cells indicate that this naturally occurring fluorescent sterol is a useful mimic for probing the properties of cholesterol in these systems.
Structure of Dehydroergosterol monohydrate and interaction with sterol carrier protein-2
Lipids 2008 Dec;43(12):1165-84.PMID:19020914DOI:10.1007/s11745-008-3267-1.
Dehydroergosterol [ergosta-5,7,9(11),22-tetraen-3beta-ol] is a naturally-occurring, fluorescent sterol utilized extensively to probe membrane cholesterol distribution, cholesterol-protein interactions, and intracellular cholesterol transport both in vitro and in vivo. In aqueous solutions, the low solubility of Dehydroergosterol results in the formation of monohydrate crystals similar to cholesterol. Low temperature X-ray diffraction analysis reveals that Dehydroergosterol monohydrate crystallizes in the space group P2(1) with four molecules in the unit cell and monoclinic crystal parameters a = 9.975(1) A, b = 7.4731(9) A, c = 34.054(4) A, and beta = 92.970(2) degrees somewhat similar to ergosterol monohydrate. The molecular arrangement is in a slightly closer packed bilayer structure resembling cholesterol monohydrate. Since Dehydroergosterol fluorescence emission undergoes a quantum yield enhancement and red-shift of its maximum wavelength when crystallized, formation or disruption of microcrystals was monitored with high sensitivity using cuvette-based spectroscopy and multi-photon laser scanning imaging microscopy. This manuscript reports on the dynamical effect of sterol carrier protein-2 (SCP-2) interacting between aqueous dispersions of Dehydroergosterol monohydrate microcrystal donors and acceptors consisting not only of model membranes but also vesicles derived from plasma membranes isolated by biochemical fractionation and affinity purification from Madin-Darby canine kidney cells. Furthermore, this study provides real-time measurements of the effect of increased SCP-2 levels on the rate of disappearance of Dehydroergosterol microcrystals in living cells.
Hybrid of Dehydroergosterol and nitrogenous alternariol derivative from the fungus Pestalotiopsis uvicola
Steroids 2018 Oct;138:43-46.PMID:30003909DOI:10.1016/j.steroids.2018.06.008.
A new hybrid of Dehydroergosterol and nitrogenous alternariol derivative, pestauvicomorpholine A (1), and three alternariol analogues (2-4) including a new aminated one, pestauvicolactone A (2), were isolated from the fermentation product of the fungus Pestalotiopsis uvicola on rice media. Compounds 1 and 2 represent the first example of aza-alternariol and aza-alternariol-steroid derived from transamination followed by intermolecular hetero-Diels-Alder reaction.
A fluorescence study of Dehydroergosterol in phosphatidylcholine bilayer vesicles
Biochemistry 1987 May 5;26(9):2441-8.PMID:3607026DOI:10.1021/bi00383a007.
The fluorescent sterol delta 5,7,9(11),22-ergostatetraen-3 beta-ol (Dehydroergosterol) was incorporated into 1-palmitoyl-2-oleoylphosphatidylcholine (POPC) small unilamellar vesicles (SUV) with and without cholesterol in order to monitor sterol-sterol interactions in model membranes. In the range 0-5 mol % fluorescent sterol, Dehydroergosterol underwent a concentration-dependent relaxation characterized by red-shifted wavelengths of maximum absorption as well as altered ratios of absorbance maxima and fluorescence excitation maxima at 338 nm/324 nm. Fluorescence intensity per mole of Dehydroergosterol increased up to 5 mol % in POPC vesicles. In contrast, quantum yield, steady-state anisotropy, limiting anisotropy, lifetime, and rotational rate remained relatively constant in this concentration range. Similarly, addition of increasing cholesterol in the range 0-5 mol % in the presence of 3 mol % Dehydroergosterol also increased the fluorescence intensity per mole of Dehydroergosterol, red-shifted wavelengths of maximum absorption, and altered ratios of absorbance maxima. In POPC vesicles containing between 5 and 33 mol % Dehydroergosterol, the fluorescent Dehydroergosterol interacted to self-quench, thereby decreasing the fluorescence intensity, quantum yield, steady-state anisotropy, and limiting anisotropy and increasing the rotational rate (decreased rotational relaxation time) of the fluorescent sterol. The fluorescence lifetime of Dehydroergosterol remained unchanged. The results were in accord with the interpretation that below 5 mol% sterol, the sterols behaved as monomers exposed to some degree to the aqueous solvent in POPC bilayers.(ABSTRACT TRUNCATED AT 250 WORDS)