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Distribution of urocanic acid isomers between aqueous solutions and n-octanol, liposomes or bovine serum albumin

Paper ID Volume ID Publish Year Pages File Format Full-Text
30408 44477 2008 6 PDF Available
Title
Distribution of urocanic acid isomers between aqueous solutions and n-octanol, liposomes or bovine serum albumin
Abstract

The distribution of urocanic acid (UCA) isomers between aqueous solutions and n-octanol, egg yolk phosphatidylcholine (eggPC) liposomes or bovine serum albumin (BSA) has been evaluated. Regarding its partitioning between water and n-octanol, the behaviour of both isomers is very similar, and the amount incorporated to the organic solvent is mostly determined by the fraction of the compound that, in the aqueous phase, is present as uncharged species. This implies that the highest hydrophobicity occurs near the isoelectric point.cis- and trans-UCA are readily incorporated into eggPC unilamellar liposomes. A simple pseudophase treatment of ultrafiltration data renders a binding constant of 0.20 ± 0.04 mL/mg for the trans isomer at pH 7.4. The binding constant decreases, by a factor two, at pH 5.0, suggesting that the negatively charged species is more favourably bound to the liposomes than the neutral species, which is mostly present as zwitterions. The cis-isomer, at both pHs, is less incorporated to the bilayers.trans-UCA and cis-UCA readily bind to BSA at pH 7.4, with binding constants of 3400 M−1 and 6900 M−1, respectively. This result suggests that, as in the octanol/water partitioning, hydrophobic interactions predominate and the degree of binding is determined by the fraction present as uncharged species. A smaller binding constant at pH 5.0 indicates that the charge of the protein is also plying a relevant role.

Keywords
Urocanic acid; Octanol/water distribution; Liposomes; Bovine serum albumin
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Distribution of urocanic acid isomers between aqueous solutions and n-octanol, liposomes or bovine serum albumin
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology B: Biology - Volume 90, Issue 1, 30 January 2008, Pages 41–46
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
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Don't Miss Today's Special Offer
Price was $35.95
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Price after discount Only $4.95
100% Money Back Guarantee
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