Highly Hydrophilic and Lipophilic Derivatives of Bile Salts
Lipophilicity of 15 derivatives of sodium cholate, defined by the octan-1-ol/water partition coefficient (<i>log P</i>), has been theoretically determined by the <i>Virtual</i> <i>log P</i> method. These derivatives bear highly hydrophobic or highly hydrophilic su...
| Main Authors: | , , , , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-06-01
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| Series: | International Journal of Molecular Sciences |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1422-0067/22/13/6684 |
| Summary: | Lipophilicity of 15 derivatives of sodium cholate, defined by the octan-1-ol/water partition coefficient (<i>log P</i>), has been theoretically determined by the <i>Virtual</i> <i>log P</i> 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 <i>log P</i> and the minimum one is enlarged to 3.5. The partition coefficient and the critical micelle concentration (<i>cmc</i>) are tightly related by a double-logarithm relationship (<inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mrow><mi>V</mi><mi>i</mi><mi>r</mi><mi>t</mi><mi>u</mi><mi>a</mi><mi>l</mi><mi>log</mi><mi>P</mi><mo>=</mo><mo>−</mo><mrow><mo>(</mo><mrow><mn>1.00</mn><mo>±</mo><mn>0.09</mn></mrow><mo>)</mo></mrow><mi>log</mi><mrow><mo>(</mo><mrow><mfrac><mrow><mi>c</mi><mi>m</mi><mi>c</mi></mrow><mrow><mi>mM</mi></mrow></mfrac></mrow><mo>)</mo></mrow><mo>+</mo><mrow><mo>(</mo><mrow><mn>2.79</mn><mo>±</mo><mn>0.09</mn></mrow><mo>)</mo></mrow></mrow></semantics></math></inline-formula>), 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 <i>cmc</i> 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<i>C<sub>P,demic</sub></i>, were obtained. Δ<i>C<sub>P,demic</sub></i>, being positive, means that the interior of the aggregates is hydrophobic. |
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| ISSN: | 1661-6596 1422-0067 |