The effect of hydroxyl moieties and their oxosubstitution on bile acid association studied in floating monolayers

M. Szekeres, B. Viskolcz, Mihalj Poša, János Csanádi, Dušan Škorić, E. Illés, Ildikó Y. Tóth, E. Tombácz

Research output: Contribution to journalArticle

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Abstract

Bile salt aggregates are promising candidates for drug delivery vehicles due to their unique fat-solubilizing ability. However, the toxicity of bile salts increases with improving fat-solubilizing capability and so an optimal combination of efficient solubilization and low toxicity is necessary. To improve hydrophilicity (and decrease toxicity), we substituted hydroxyl groups of several natural bile acid (BA) molecules for oxogroups and studied their intrinsic molecular association behavior. Here we present the comparative Langmuir trough study of the two-dimensional (2D) association behavior of eight natural BAs and four oxoderivatives (traditionally called keto-derivatives) floated on an aqueous subphase. The series of BAs and derivatives showed systematic changes in the shape of the compression isotherms. Two types of association could be distinguished: the first transition was assigned to the formation of dimers through H-bonding and the second to the hydrophobic aggregation of BA dimers. Hydrophobic association of BA molecules in the films is linked to the ability of forming H-bonded dimers. Both H-bond formation and hydrophobic association weakened with increasing number of hydroxyl groups, decreasing distance between hydroxyl groups, and increasing oxosubstitution. The results also show that the Langmuir trough method is extremely useful in selecting appropriate BA molecules to design drug delivery systems.

Original languageEnglish
Article number152972
JournalTheScientificWorldJournal [electronic resource]
Volume2014
DOIs
Publication statusPublished - 2014

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Bile Acids and Salts
Hydroxyl Radical
Monolayers
acid
toxicity
Dimers
fat
Toxicity
trough
drug
salt
Molecules
solubilization
Fats
Derivatives
isotherm
compression
Hydrophilicity
Drug Delivery Systems
Drug delivery

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Environmental Science(all)
  • Medicine(all)

Cite this

The effect of hydroxyl moieties and their oxosubstitution on bile acid association studied in floating monolayers. / Szekeres, M.; Viskolcz, B.; Poša, Mihalj; Csanádi, János; Škorić, Dušan; Illés, E.; Tóth, Ildikó Y.; Tombácz, E.

In: TheScientificWorldJournal [electronic resource], Vol. 2014, 152972, 2014.

Research output: Contribution to journalArticle

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AU - Viskolcz, B.

AU - Poša, Mihalj

AU - Csanádi, János

AU - Škorić, Dušan

AU - Illés, E.

AU - Tóth, Ildikó Y.

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