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高度亲水和亲脂的胆汁盐衍生物。

Highly Hydrophilic and Lipophilic Derivatives of Bile Salts.

机构信息

Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Santiago de Compostela, Avda. Alfonso X El Sabio s/n, 27002 Lugo, Spain.

Departamento de Química Física, Facultad de Ciencias, Universidad de Santiago de Compostela, Avda. Alfonso X El Sabio s/n, 27002 Lugo, Spain.

出版信息

Int J Mol Sci. 2021 Jun 22;22(13):6684. doi: 10.3390/ijms22136684.

DOI:10.3390/ijms22136684
PMID:34206572
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8268814/
Abstract

Lipophilicity of 15 derivatives of sodium cholate, defined by the octan-1-ol/water partition coefficient (), has been theoretically determined by the   method. These derivatives bear highly hydrophobic or highly hydrophilic substituents at the C3 position of the steroid nucleus, being linked to it through an amide bond. The difference between the maximum value of and the minimum one is enlarged to 3.5. The partition coefficient and the critical micelle concentration () are tightly related by a double-logarithm relationship (VirtuallogP=-(1.00±0.09)log(cmcmM)+(2.79±0.09)), meaning that the Gibbs free energies for the transfer of a bile anion from water to either a micelle or to octan-1-ol differ by a constant. The equation also means that can be used as a measurement of lipophilicity. The demicellization of the aggregates formed by three derivatives of sodium cholate bearing bulky hydrophobic substituents has been studied by surface tension and isothermal titration calorimetry. Aggregation numbers, enthalpies, free energies, entropies, and heat capacities, Δ, were obtained. Δ, being positive, means that the interior of the aggregates is hydrophobic.

摘要

通过   方法理论上确定了 15 种胆酸钠衍生物的脂溶性，由辛醇/水分配系数 () 定义。这些衍生物在甾体核的 C3 位置带有高度疏水性或高度亲水性取代基，通过酰胺键与之相连。最大 值和最小 值之间的差异扩大到 3.5。分配系数和临界胶束浓度 () 通过双对数关系（VirtuallogP=-(1.00±0.09)log(cmcmM)+(2.79±0.09)）紧密相关，这意味着胆汁阴离子从水转移到胶束或辛醇的吉布斯自由能相差一个常数。该方程还意味着 可以用作脂溶性的测量。通过表面张力和等温滴定量热法研究了带有大体积疏水性取代基的 3 种胆酸钠衍生物形成的聚集体的去胶束化。获得了聚集数、焓、自由能、熵和热容量 Δ。Δ 为正值，这意味着聚集体的内部是疏水的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/95bf/8268814/4251d0e3a4da/ijms-22-06684-g006.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/95bf/8268814/ed4fc7cd819b/ijms-22-06684-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/95bf/8268814/40b5bdd163fa/ijms-22-06684-g002a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/95bf/8268814/7630cec51365/ijms-22-06684-g003.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/95bf/8268814/4251d0e3a4da/ijms-22-06684-g006.jpg

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