Study of interaction of carprofen and its enantiomers with human serum albumin--I. Mechanism of binding studied by dialysis and spectroscopic methods

Biochemical Pharmacology
M H RahmanM Otagiri

Abstract

The binding of carprofen, a non-steroidal anti-inflammatory drug of the aryl propionic acid class [2-(6-chlorocarbazole)propionic acid], and its enantiomers to human serum albumin (HSA) has been studied by dialysis and spectroscopic methods. Binding parameters obtained by different methods were in close agreement. The binding of carprofen to HSA by both fluorescence and equilibrium dialysis (ED) methods is characterized by two sets of association constants [K1 = 5.1 x 10(6) M-1 (fluorescence) and 3.7 x 10(6) M-1 (ED), K2 = 3.7 x 10(5) M-1 (fluorescence) and 1.3 x 10(5) M-1 (ED)]. The S(+)-enantiomer of carprofen showed slightly higher affinity for HSA than its corresponding antipode by both methods. Different analyses of the binding to HSA suggested the presence of one high affinity site and five to seven low affinity sites for carprofen and its enantiomers on HSA. Fluorescence displacement data implied that carprofen primarily binds to site II, the benzodiazepine site, while the low affinity site of carprofen is site I, the warfarin site. Circular dichroism data suggested different mechanisms for the high affinity and the low affinity binding of carprofen to HSA. The data are consistent with the major part of the binding energ...Continue Reading

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