HPLC study on ion-pairing ability of deoxycholic acid epimers

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Abstract

In line with the postulate that the physiological functions of bile acids, in particular their contribution to the regulation of the fat metabolism, may be related to their ion-pairing ability, this paper provides data on the chromatographic aspects related to their ion-pairing ability. The paper provides data about the chromatographic aspects of this subject. The ion-pairing (i.e. HPLC-retention-increasing) effects of the therapeutically applied deoxycholic acid epimers (7-deoxycholic acid, DOC; chenodeoxycholic acid, ChDOC; and ursodeoxycholic acid, UDOC) were studied in a reversed-phase HPLC system. As cationic partner substances, nine quaternary ammonium drug compounds were used as cationic partners The ion-pairing activities of the deoxycholic acids were found to be very strong, and much better than those of anionic ion-pairing agents such as pentanesulfonic acid and caproic acid. The natures of the binding of the DOC epimers by the C18 surface were also determined. While DOC and ChDOC formed double layers on the surface, UDOC was bound only in a monolayer. The differences in chromatographic behavior are interpreted on a stereochemical basis.

Original languageEnglish
Pages (from-to)173-185
Number of pages13
JournalJournal of Liquid Chromatography and Related Technologies
Volume24
Issue number2
DOIs
Publication statusPublished - 2001

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Deoxycholic Acid
High Pressure Liquid Chromatography
Ions
Quaternary Ammonium Compounds
Chenodeoxycholic Acid
Ursodeoxycholic Acid
Bile Acids and Salts
Ammonium Compounds
Metabolism
Monolayers
Fats
Acids
Pharmaceutical Preparations

ASJC Scopus subject areas

  • Analytical Chemistry
  • Clinical Biochemistry

Cite this

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title = "HPLC study on ion-pairing ability of deoxycholic acid epimers",
abstract = "In line with the postulate that the physiological functions of bile acids, in particular their contribution to the regulation of the fat metabolism, may be related to their ion-pairing ability, this paper provides data on the chromatographic aspects related to their ion-pairing ability. The paper provides data about the chromatographic aspects of this subject. The ion-pairing (i.e. HPLC-retention-increasing) effects of the therapeutically applied deoxycholic acid epimers (7-deoxycholic acid, DOC; chenodeoxycholic acid, ChDOC; and ursodeoxycholic acid, UDOC) were studied in a reversed-phase HPLC system. As cationic partner substances, nine quaternary ammonium drug compounds were used as cationic partners The ion-pairing activities of the deoxycholic acids were found to be very strong, and much better than those of anionic ion-pairing agents such as pentanesulfonic acid and caproic acid. The natures of the binding of the DOC epimers by the C18 surface were also determined. While DOC and ChDOC formed double layers on the surface, UDOC was bound only in a monolayer. The differences in chromatographic behavior are interpreted on a stereochemical basis.",
author = "G. Sz{\'a}sz and K. Tak{\'a}cs-Nov{\'a}k and J. K{\"o}k{\"o}si",
year = "2001",
doi = "10.1081/JLC-100001480",
language = "English",
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journal = "Journal of Liquid Chromatography and Related Technologies",
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AU - Szász, G.

AU - Takács-Novák, K.

AU - Kökösi, J.

PY - 2001

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N2 - In line with the postulate that the physiological functions of bile acids, in particular their contribution to the regulation of the fat metabolism, may be related to their ion-pairing ability, this paper provides data on the chromatographic aspects related to their ion-pairing ability. The paper provides data about the chromatographic aspects of this subject. The ion-pairing (i.e. HPLC-retention-increasing) effects of the therapeutically applied deoxycholic acid epimers (7-deoxycholic acid, DOC; chenodeoxycholic acid, ChDOC; and ursodeoxycholic acid, UDOC) were studied in a reversed-phase HPLC system. As cationic partner substances, nine quaternary ammonium drug compounds were used as cationic partners The ion-pairing activities of the deoxycholic acids were found to be very strong, and much better than those of anionic ion-pairing agents such as pentanesulfonic acid and caproic acid. The natures of the binding of the DOC epimers by the C18 surface were also determined. While DOC and ChDOC formed double layers on the surface, UDOC was bound only in a monolayer. The differences in chromatographic behavior are interpreted on a stereochemical basis.

AB - In line with the postulate that the physiological functions of bile acids, in particular their contribution to the regulation of the fat metabolism, may be related to their ion-pairing ability, this paper provides data on the chromatographic aspects related to their ion-pairing ability. The paper provides data about the chromatographic aspects of this subject. The ion-pairing (i.e. HPLC-retention-increasing) effects of the therapeutically applied deoxycholic acid epimers (7-deoxycholic acid, DOC; chenodeoxycholic acid, ChDOC; and ursodeoxycholic acid, UDOC) were studied in a reversed-phase HPLC system. As cationic partner substances, nine quaternary ammonium drug compounds were used as cationic partners The ion-pairing activities of the deoxycholic acids were found to be very strong, and much better than those of anionic ion-pairing agents such as pentanesulfonic acid and caproic acid. The natures of the binding of the DOC epimers by the C18 surface were also determined. While DOC and ChDOC formed double layers on the surface, UDOC was bound only in a monolayer. The differences in chromatographic behavior are interpreted on a stereochemical basis.

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