The effect of octanoic acid on the binding of the enantiomers of ibuprofen and naproxen to human serum albumin: a chromatographic implication.
OBJECTIVE
The heats of reaction between the enantiomers and racemates of ibuprofen and naproxen and human serum albumin (HSA) are to be measured with and without the addition of octanoic acid. The effects of octanoic acid on the free energies of interaction between the drugs and HSA is to be determined and compared to that estimated from theoretical equations.


METHODS
The heats of reaction have been measured directly by flow microcalorimetry.


RESULTS
The data showed that octanoic acid lowered the 1:1 binding constants for all the drug-HSA interactions investigated. The effect of octanoic acid was greater on the R than on the S forms of the drugs as shown by the differences in free energies of interaction in the presence and absence of octanoic acid.


CONCLUSIONS
The increased free energy differences for the binding of the enantiomers of both drugs to HSA in the presence of octanoic acid is closer to the value deemed to be necessary for the separation of enantiomers by Davenkov, and shows the importance of the addition of octanoic acid to the mobile phase in the separation of these enantiomers on immobilized albumin columns.
Cheruvallath
V K
VK
Department of Pharmaceutical Chemistry, University of Kansas, Lawrence 66046, USA.
Riley
C M
CM
Narayanan
S R
SR
Lindenbaum
S
S
Perrin
J H
JH
D002151:Calorimetry; D002210:Caprylates / Q000737:chemistry*; D002845:Chromatography; D007052:Ibuprofen / Q000737:chemistry*; D009288:Naproxen / Q000737:chemistry*; D011485:Protein Binding; D012709:Serum Albumin / Q000737:chemistry*; D013237:Stereoisomerism; D013816:Thermodynamics
D002210:Caprylates; D012709:Serum Albumin; D009288:Naproxen; C031492:octanoic acid; D007052:Ibuprofen