Bile acid structure-activity relationship: evaluation of bile acid lipophilicity using 1-octanol/water partition coefficient and reverse phase HPLC.

Roda, Aldo; Minutello, A.; Angellotti, M. A.; Fini, Adamo

doi:10.1016/s0022-2275(20)42614-8

Cited by 187 publications

(49 citation statements)

References 33 publications

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“…As expected, hydrophobicity increases with the reduction of BAs. CA has a partition coefficient of 2.02, which increases to 3.28 when CA is reduced to CDCA and further increases to 3.5 when reduced to DCA [ 93 ]. The conjugation of both glycine and taurine to any sterol significantly increases the hydrophilicity of the compound, thus decreasing the partition coefficient for each BA.…”

Section: Molecular Diversity Of Microbially Conjugated Bile Acidsmentioning

confidence: 99%

Review: microbial transformations of human bile acids

2021

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Bile acids play key roles in gut metabolism, cell signaling, and microbiome composition. While the liver is responsible for the production of primary bile acids, microbes in the gut modify these compounds into myriad forms that greatly increase their diversity and biological function. Since the early 1960s, microbes have been known to transform human bile acids in four distinct ways: deconjugation of the amino acids glycine or taurine, and dehydroxylation, dehydrogenation, and epimerization of the cholesterol core. Alterations in the chemistry of these secondary bile acids have been linked to several diseases, such as cirrhosis, inflammatory bowel disease, and cancer. In addition to the previously known transformations, a recent study has shown that members of our gut microbiota are also able to conjugate amino acids to bile acids, representing a new set of “microbially conjugated bile acids.” This new finding greatly influences the diversity of bile acids in the mammalian gut, but the effects on host physiology and microbial dynamics are mostly unknown. This review focuses on recent discoveries investigating microbial mechanisms of human bile acids and explores the chemical diversity that may exist in bile acid structures in light of the new discovery of microbial conjugations.

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Section: Molecular Diversity Of Microbially Conjugated Bile Acidsmentioning

confidence: 99%

Review: microbial transformations of human bile acids

2021

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“…Let us remember that, established on an empirical basis, HLB has been used in emulsion technology. As mentioned earlier, the coefficient of partition (log P) of a molecule between octan-1-ol and water [8] has been used to express the lipophilicity of bile acids and their salts [9]. Davies [44] proposed an equation which relates HLB with P, thus allowing for "an extrathermodynamic significance to each structural element in determining the molecule's ability to function as a wetting agent, detergent, or defoamer" [7].…”

Section: Resultsmentioning

confidence: 99%

“…However, it also depends on the bulky environment properties as pH [12]. On the other hand, Roda et al [9] have shown that both the protonated and ionized forms of bile acids can distribute in octan-1-ol, and con-sequently, a partition coefficient for each form must be defined. The difference between both values is almost constant with an average value of 0.91 ± 0.09 (log P units).…”

Section: Resultsmentioning

confidence: 99%

“…Table 2 shows the calculated values by the indicated methods together with the experimental values from Roda et al [9] for natural unconjugated bile acids. The first two rows (NaC and NaHC) correspond to trihydroxy derivatives and the remaining rows to dihydroxy ones.…”

Section: Resultsmentioning

confidence: 99%

“…The partition coefficient has been used to express the lipophilicity of bile acids and their salts [8,9]. Roda et al [8,9] have experimentally determined the log P values for natural bile acids and their taurine and glycine conjugates, showing that it depends on the number, position, and orientation of hydroxyl groups. This dependence is also demonstrated by the retention parameters of reverse-phase chromatography [10,11].…”

Section: Introductionmentioning

confidence: 99%

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Highly Hydrophilic and Lipophilic Derivatives of Bile Salts

Vázquez-Tato

Seijas

Meijide

et al. 2021

IJMS

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Lipophilicity of 15 derivatives of sodium cholate, defined by the octan-1-ol/water partition coefficient (log P), has been theoretically determined by the Virtual log P 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 log P and the minimum one is enlarged to 3.5. The partition coefficient and the critical micelle concentration (cmc) 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 cmc 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, ΔCP,demic, were obtained. ΔCP,demic, being positive, means that the interior of the aggregates is hydrophobic.

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Enantiomeric resolution of some nonsteroidal antiinflammatory and anticoagulant drugs using ?-cyclodextrins by capillary electrophoresis

et al. 1999

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β‐cyclodextrin (CD) and its derivatives HP‐β‐CD, DM‐β‐CD, and TM‐β‐CD have been employed as chiral selectors for the separation of three nonsteroidal antiinflammatory drugs (NSAIDs) and anticoagulant at relatively low concentration (8–15 mM) by capillary zone electrophoresis (CZE). In this study, baseline separation was achieved for ibuprofen, ketoprofen, naproxen, and warfarin. It was found that the addition of 0.1% hydroxypropyl methyl cellulose (HPMC) was effective for separation. Under these conditions, the S‐(+) enantiomer eluted before R‐(−) in terms of ibuprofen; the calculated energy values obtained from the molecular modeling correlated well with the elution order. An equation for calculating the pKa values by capillary electrophoresis was introduced, and the pKa values of the four chiral drugs at 25°C were obtained based on the equation. The value pKa + 0.5 is proposed to be the suitable pH of the background electrolyte for the separation of chiral compounds containing a carboxylic group. Chirality 11:56–62, 1999. © 1999 Wiley‐Liss, Inc.

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Bile acid structure-activity relationship: evaluation of bile acid lipophilicity using 1-octanol/water partition coefficient and reverse phase HPLC.

Cited by 187 publications

References 33 publications

Review: microbial transformations of human bile acids

Review: microbial transformations of human bile acids

Highly Hydrophilic and Lipophilic Derivatives of Bile Salts

Enantiomeric resolution of some nonsteroidal antiinflammatory and anticoagulant drugs using ?-cyclodextrins by capillary electrophoresis

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