Octaethylene glycol monododecyl ether (C12E8)   中文名称: 月桂醇聚醚-8

Non-ionic detergent

已经证明，完整的流感病毒膜可以被八乙二醇单十二烷基醚（C12E8）溶解。 C12E8 分子在膜外积累直至形成胶束，从而可以提取膜内容物，这为病毒膜溶解机制提供了基础[1]。

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通过表面张力和电导率测量研究了二正癸基二甲基氯化铵[DiC10][Cl]和八乙二醇单十二烷基醚C12E8混合物的胶束化。根据这些结果，详细评估和讨论了各种物理化学和热力学关键参数（如[DiC10][Cl]的胶束摩尔分数、相互作用参数、胶束化自由能等）。结果表明，两种表面活性剂之间具有很高的协同效应。基于这些结果，研究了[DiC10][Cl]和C12E8等摩尔混合物的杀病毒活性。在含脂质的脱氧核糖核酸和核糖核酸病毒上观察到明显的协同作用，如疱疹病毒、呼吸道合胞病毒和痘苗病毒。相比之下，柯萨奇病毒（无包膜病毒）没有灭活。这些结果支持该机制基于从混合胶束内的包膜中提取脂质和/或蛋白质。这种提取会产生“孔”，其大小随着浓度的增加而增加，直至达到特定值，从而触发病毒失活。这种混合物可用于扩展许多消毒剂溶液中常用的两亲性杀病毒剂的杀病毒活性谱。[1]

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利用光散射和荧光探针技术研究了分别属于烷基糖苷和聚氧乙烯烷基醚家族的两种非离子表面活性剂正辛基-β-D-硫代葡萄糖苷（OTG）和八乙二醇单十二烷基醚（C12E8）的混合胶束。通过成熟的芘1:3比法测定临界胶束浓度（cmc），发现混合体系表现理想，胶束化过程明显受乙氧基化表面活性剂的控制。通过动态光散射测量获得了胶束流体动力学半径随温度、组成和浓度的变化。观察到胶束尺寸随温度增加而增加，随着乙氧基化表面活性剂相对比例的增加，这种增长更加明显。还发现胶束尺寸与表面活性剂总浓度的关系取决于温度和组成。随着糖表面活性剂的加入，乙氧基化表面活性剂特有的浑浊温度升高。最后，通过稳态荧光各向异性结合疏水探针香豆素6（C6）的时间分辨荧光研究，检查了胶束栅栏层中可能的结构变化。所得结果表明，乙氧基化表面活性剂的参与诱导了一个稍微更具极性的栅栏层，而探针由于环境不太紧凑而进行了更快的旋转重新取向。所有这些观察结果都归因于两种表面活性剂头部基团的不同结构，因此也归因于它们不同的水合作用[2]。

病毒灭活[1]
将200μL病毒储备溶液加入200μL纯表面活性剂（C12E8或[DiC10][Cl]）或200μLC12E8和[DiC10][Cl]的二元水混合物（等摩尔比例）中。在室温下孵育15分钟后，立即在MicroSpin S-400 HR柱上过滤混合物，以将病毒与混合物的其他成分分离。然后如上所述滴定残留病毒。每个实验至少进行三次。

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本次调查中使用的表面活性剂样品与我们早期研究中使用的样品相同。荧光探针芘和香豆素6（C6）（激光级，Exciton）具有高纯度，因此按原样使用。制备了不同比例的含有OTG和C12E8的不同水性储备溶液。溶液的本体组成以乙氧基化表面活性剂α2的摩尔分数表示，定义为：， 其中[C12E8]和[OTG]分别是C12E8和OTG的摩尔浓度。荧光探针的储备溶液在无水乙醇中制备，并储存在4°C下。每天制备较低浓度的工作溶液，并在制备后立即使用。用于制备所有溶液的超纯水（电阻率约为18 MΩcm）是通过将去离子水通过超高质量净化系统（UHQ-PS、ELGA）获得的[2]。

病毒和细胞[1]
HSV-1（Kos株）和VACV（Elstree株）在Vero细胞（ATCC®CCL-81）中繁殖⿢) 在补充有2mM l-谷氨酰胺、1%非必需氨基酸和2%灭活胎牛血清的最低必需培养基中。通过冻融循环获得病毒的无细胞病毒悬浮液，然后进行低速离心以去除细胞碎片。在相同的培养基中，将非常抗性的无包膜CVB4（JVB菌株）在BGM细胞中繁殖。呼吸道合胞病毒（当地实验室菌株）在Hep-2细胞（ATCC®CCL-23）中繁殖⿢) 在同一媒介中。通过含病毒样品的连续稀释液（1:10）对Vero、Hep-2或BGM细胞的细胞病变效应来测定病毒滴度。每种稀释液的样品（100μL）用于感染96孔微量滴定板中的四个重复孔。在37°C±0.1°C的湿度为5%的CO2环境中孵育5天后，对病毒诱导的细胞病变效应进行评分。根据Spearman和Kärber的研究（Spearman，1908，Kärber，1931），滴度表示为感染50%组织培养孔的病毒数量（组织培养感染剂量，TCID50）。检测限为5.62 TCID50/mL。病毒储备为2-107 TCID50 mL⿿1 对于HSV-1，2ÿ106 TCID50 mL⿿1 对于VACV，3ÿ106 TCID50 mL⿿1 对于呼吸道合胞病毒，6ÿ106 TCID50 mL⿿1 对于CVB4。

[1]. Aqueous solutions of didecyldimethylammonium chloride and octaethylene glycol monododecyl ether: Toward synergistic formulations against enveloped viruses. Int J Pharm. 2016 Sep 10;511(1):550-559.

[2]. Characterization of mixed non-ionic surfactants n-octyl-β-D-thioglucoside and octaethylene-glycol monododecyl ether: micellization and microstructure. J Colloid Interface Sci. 2011 Sep 1;361(1):178-85.

Octaethyleneglycol monododecyl ether is the hydroxypolyether that is octaethylene glycol in which one of the hydroxy groups is substituted by dodecyloxy. It is functionally related to an octaethylene glycol.

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In the present study, micellization of [DiC10][Cl] and C12E8 mixtures have been investigated by surface tension and conductivity measurements. The surface tension data have been treated from Clint, Rubingh and Maeda models in order to access to various physicochemical and thermodynamic key parameters (e.g. micellar mole fraction of [DiC10][Cl], interaction parameter, free energy of micellization, etc.). The results highlight a high synergistic effect between the two surfactants in term of micellization especially for an equimolar mixture of [DiC10][Cl] and C12E8. This mixture also shows a wide spectrum of virucidal activity with a marked synergism against deoxyribonucleic and ribonucleic acid viruses which contain lipids in their outercoat (HSV-1, RSV, and VACV). In contrast, non-enveloped virus (CVB4) was not inactivated. Those supports that the virucidal mechanism is based on the solubilization of lipid and/or protein envelope inside mixed micelles. This solubilization creates ⿿holes⿿ whose size increases with the concentration until to a specific concentration (named minimum virucidal concentration that corresponds to end point of activity) which leads to virus inactivation. In view of our new findings that an enhancement of virucidal activity occurs with [DiC10][Cl]/C12E8 mixtures, it becomes clearly evident that the physicochemical data and the competition with biological processes must be rationalized in order to explain the additivity, synergism or antagonism behaviors observed in the simultaneous activity of two biocidal agents in vitro. Moreover, such mixtures could be used to boost the virucidal activity of other amphiphilic virucides commonly employed in various disinfectant formulations. Indeed, synergism is particularly interesting both for the formulator and the user in the fight against viruses and other nosocomial infections.[1]

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The results obtained here for the system formed by a sugar-based surfactant (OTG) and a conventional ethylene oxide one (C12E8) indicate an ideal behavior of the mixed system, which is mainly controlled by the ethoxylated surfactant. We have also found that the micellar size increases with temperature for systems rich in C12E8, but the extension of this growth strongly depends on the system composition. It was found that the addition of the sugar-based surfactant increased the cloud temperature, the cloudy being inhibited in mixtures with a high content of this surfactant. The observed growth of micelles with concentration was also dependent on temperature and system composition. These results were explained on the basis of the higher conformational flexibility of the POE segments of C12E8, allowing not only a greater amount of water penetration, but also a favorable packing with the more rigid head groups of the sugar surfactant. The photophysical and dynamic behavior of a neutral probe, C6, residing in the micellar palisade layer, corroborates that the participation of the ethoxylated surfactant induces the formation of less compact and hydrophobic micelles.
All these observations are important for two reasons. On the one hand, our results support recent findings in related mixed systems, which indicate that the observed properties can be explained on the basis of different hydration and flexibilities of the head groups and the higher surface activity of the ethoxylated surfactant. On the other, we have demonstrated how the physicochemical properties of the system can be modulated, which is important in practice, because by adjusting the proportions of both surfactants we can obtain suitable systems to cover a wide range of process requirements. [2]

C28H58O9

538.75

538.408

3055-98-9

123921

Colorless to light yellow liquid

1.0±0.1 g/cm3

585.5±45.0 °C at 760 mmHg

30ºC

307.9±28.7 °C

0.0±3.7 mmHg at 25°C

1.459

2.54

94.07

1

9

34

37

389

0

CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCO

YYELLDKEOUKVIQ-UHFFFAOYSA-N

InChI=1S/C28H58O9/c1-2-3-4-5-6-7-8-9-10-11-13-30-15-17-32-19-21-34-23-25-36-27-28-37-26-24-35-22-20-33-18-16-31-14-12-29/h29H,2-28H2,1H3

2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol

3055-98-9; Octaethyleneglycol monododecyl ether; C12E8; 3,6,9,12,15,18,21,24-Octaoxahexatriacontan-1-ol; dodecyloctaethyleneglycol monoether; O-DODECANYL OCTAETHYLENE GLYCOL; Octaethyleneglycol-dodecylmonoether; n-Dodecyl octaethylene glycol monoether;

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

H2O : ~100 mg/mL (~186 mM)
DMSO : ~100 mg/mL (~186 mM)

配方 1 中的溶解度: ≥ 2.5 mg/mL (4.64 mM) (饱和度未知) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将100 μL 25.0 mg/mL澄清DMSO储备液加入到400 μL PEG300中，混匀；然后向上述溶液中加入50 μL Tween-80，混匀；加入450 μL生理盐水定容至1 mL。
*生理盐水的制备：将 0.9 g 氯化钠溶解在 100 mL ddH₂O中，得到澄清溶液。

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配方 2 中的溶解度: ≥ 2.5 mg/mL (4.64 mM) (饱和度未知) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将 100 μL 25.0 mg/mL澄清DMSO储备液加入900 μL 20% SBE-β-CD生理盐水溶液中，混匀。
*20% SBE-β-CD 生理盐水溶液的制备（4°C，1 周）：将 2 g SBE-β-CD 溶解于 10 mL 生理盐水中，得到澄清溶液。

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配方 3 中的溶解度: ≥ 2.5 mg/mL (4.64 mM) (饱和度未知) in 10% DMSO + 90% Corn Oil (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将 100 μL 25.0 mg/mL 澄清 DMSO 储备液加入到 900 μL 玉米油中并混合均匀。

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请根据您的实验动物和给药方式选择适当的溶解配方/方案：
1、请先配制澄清的储备液(如：用DMSO配置50 或 100 mg/mL母液(储备液));
2、取适量母液，按从左到右的顺序依次添加助溶剂，澄清后再加入下一助溶剂。以 下列配方为例说明 (注意此配方只用于说明，并不一定代表此产品 的实际溶解配方):
10% DMSO → 40% PEG300 → 5% Tween-80 → 45% ddH2O (或 saline);
假设最终工作液的体积为 1 mL, 浓度为5 mg/mL: 取 100 μL 50 mg/mL 的澄清 DMSO 储备液加到 400 μL PEG300 中，混合均匀/澄清；向上述体系中加入50 μL Tween-80，混合均匀/澄清；然后继续加入450 μL ddH2O (或 saline)定容至 1 mL；
3、溶剂前显示的百分比是指该溶剂在最终溶液/工作液中的体积所占比例;
4、 如产品在配制过程中出现沉淀/析出，可通过加热(≤50℃)或超声的方式助溶;
5、为保证最佳实验结果，工作液请现配现用！
6、如不确定怎么将母液配置成体内动物实验的工作液，请查看说明书或联系我们;
7、 以上所有助溶剂都可在 Invivochem.cn网站购买。