Stereoselective binding and degradation of sulbenicillin in the presence of human serum albumin

Chirality
Y TsudaT Itoh

Abstract

Binding of sulbenicillin (SBPC) isomers to human serum albumin (HSA) was stereoselective. There were at least two classes of binding sites on HSA for SBPC isomers. At the stereoselective high affinity site, binding was in favor of R-SBPC, the binding constant of R-SBPC being approximately 2.3-fold greater than that of S-SBPC. By using site marker ligands, it was revealed that the stereoselective site was Site I (warfarin binding site). Affinity for the low affinity (nonstereoselective) site was similar for the diastereomers, approximately 7--30-fold lower than for the stereoselective site. R-SBPC and S-SBPC appeared to displace each other competitively at both binding sites. On the other hand, R-SBPC was degraded much faster than S-SBPC in the presence of HSA, with a degradation rate constant approximately 7-fold greater for R-SBPC than for S-SBPC. The degradation of R-SBPC was inhibited in the presence of warfarin and dependent on the concentration of R-SBPC bound to Site I. The results demonstrate that Site I is responsible for the stereoselective degradation.

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Citations

Mar 12, 2004·Journal of Pharmaceutical and Biomedical Analysis·Y F CuiM L Liu
Jun 26, 2002·Biological & Pharmaceutical Bulletin·Ulrich Kragh-HansenMasaki Otagiri
Mar 31, 2005·Rapid Communications in Mass Spectrometry : RCM·Zhongzhou ShenStella Vincent
Nov 19, 2008·Biomedical Chromatography : BMC·Laura Escuder-GilabertMaría José Medina-Hernández
Aug 2, 2016·Biological & Pharmaceutical Bulletin·Akitoshi TatsumiSeigo Iwakawa
Nov 28, 2017·Biological & Pharmaceutical Bulletin·Akitoshi TatsumiSeigo Iwakawa

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