J. Lipid Res.
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A more recent version of this article appeared on March 1, 2005

Papers In Press, published online ahead of print December 16, 2004
J. Lipid Res., doi:10.1194/jlr.M400439-JLR200
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Submitted on November 3, 2004
Revised on December 16, 2004
Accepted on December 5, 2004

Interfacial properties of most monofluorinated bile acids deviate markedly from the natural congeners: studies with the Langmuir-Pockels surface balance

John M. Kauffman, Roberto Pellicciari, and Martin C. Carey

Department of Gastroenterology, Brigham and Women's Hospital, Boston, MA 02115

Corresponding Author: mccarey{at}rics.bwh.harvard.edu

We characterized the air-water interfacial properties of four monofluorinated bile acids alone and in binary mixtures with a common lecithin, 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) employing an automated Langmuir-Pockels surface balance. We compared 7a-fluoromurocholic acid (FMCA), 7a-fluorohyodeoxycholic acid (FHDCA), 6a-fluoroursodeoxycholic acid (FUDCA) and 6a-fluorochenodeoxycholic acid (FCDCA) with their natural dihydroxy homologues, murocholic acid (MCA), hyodeoxycholic acid (HDCA), ursodeoxycholic acid (UDCA) and chenodeoxycholic acid (CDCA). For further comparison, two trihydroxy bile acids, 3a-, 6b-, 7a-trihydroxycholanoic acid (a-muricholic acid, a-MCA) and 3a-, 6a-, 7b-trihydroxycholanoic acid (w-muricholic acid, w-MCA) with isologous OH polar functions to FMCA and FUDCA were also studied. Pressure (p)-area (A) isotherms of MCA, HDCA, UDCA, CDCA, as well as FMCA displayed sharp collapse points. In contrast, FHDCA, FUDCA and FCDCA formed monolayers that were less stable than the trihydroxy bile acids displaying second-order phase transitions in their isotherms. All natural and fluorinated bile acids condensed mixed monolayers with POPC, with maximal effects at molar bile acid concentrations between 30 and 50 mol %. Examination of molecular models revealed that the 7a-F atom of the interfacially stable FMCA projects away from the 6b-OH function, resulting in minimal steric interactions, whereas in FHDCA, FUDCA, and FCDCA, close vicinal interactions between OH and F polar functions result in progressive bulk solubility upon monolayer compression. These results provide a framework for designing F-modified bile acids to mimic or diverge from the natural compounds in vivo.


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