Improving the oral bioavailability of the iron chelator HBED by breaking the symmetry of the intramolecular H-bond network

…, C Spanka, T Sergejew, V Tschinke

Index: Faller, Bernard; Spanka, Carsten; Sergejew, Thomas; Tschinke, Vincenzo Journal of Medicinal Chemistry, 2000 , vol. 43, # 8 p. 1467 - 1475

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Citation Number: 32

Abstract

Physicochemical analysis and Monte Carlo simulations were used to identify structural features which prevent oral absorption of HBED, a potent iron chelator. In water the dominant conformations of HBED involve the hydrophobic collapse of the two aromatic rings. These conformations are favored in polar media because they expose the polar phenolic hydroxy groups to the solvent and partially shield the nonpolar aromatic rings. In ...