NDLI: Interaction of Amino Acid and Dipeptide β-Naphthylamide Derivatives with Hyaluronic Acid and Human Serum Albumin Studied by Capillary Electrophoresis Frontal Analysis

Content Provider	Springer Nature Link
Author	Ye, Fengbin Xie, Yuanyi Jensen, Henrik Larsen, Susan Weng Yaghmur, Anan Larsen, Claus Østergaard, Jesper
Copyright Year	2012
Abstract	Interactions of drug candidates with the biomacromolecules of the synovial fluid affect drug targeting to the articular cartilage as well as clearance from the synovial space upon intra-articular administration. Hyaluronic acid (HA) and human serum albumin (HSA) are two main components existing in the synovial fluid. To this end, we investigated the affinity of seven cationic amino acid and dipeptide β-naphthylamide derivatives towards HA and HSA in order to shed light on possible relationships between physicochemical properties, in particular charge state, and biomacromolecular interactions to increase the joint residence time. Capillary electrophoresis frontal analysis was used for characterization of the binding of the derivatives to hyaluronic acid and HSA at 25 °C in acetate buffer (pH 4.65) and phosphate buffer (pH 7.40), respectively. Linear binding isotherms were observed for the ligand–hyaluronic acid interactions and the obtained binding constants ranged from 43 to 133 M−1. The average fraction of bound ligand towards hyaluronic acid increased with increasing the net charge of the ligands but was less than 67 % for all investigated ligands. The obtained binding constants of the ligands with HSA varied in the range of 103–106 M−1. The interactions of low-molecular weight derivatives with hyaluronic acid were highly dependent on the ligand charge state. This trend was not observed for the interactions with HSA. The obtained affinity data may provide useful information in the design of cartilage adhesive prodrugs with extended residence time in the synovial cavity.
Starting Page	49
Ending Page	57
Page Count	9
File Format	PDF
ISSN	00095893
Journal	Chromatographia
Volume Number	76
Issue Number	1-2
e-ISSN	16121112
Language	English
Publisher	Springer-Verlag
Publisher Date	2012-12-12
Publisher Place	Berlin, Heidelberg
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Affinity capillary electrophoresis Frontal analysis Binding constant Electrostatic interaction Hyaluronic acid Human serum albumin Chromatography Proteomics Pharmacy Laboratory Medicine
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Analytical Chemistry Biochemistry Clinical Biochemistry

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