β-Naphthoflavone analogs as potent and soluble aryl hydrocarbon receptor agonists: Improvement of solubility by disruption of molecular planarity

…, M Yonehara, M Tetsuhashi, T Noguchi-Yachide…

Index: Fujita, Yuji; Yonehara, Mitsuhiro; Tetsuhashi, Masashi; Noguchi-Yachide, Tomomi; Hashimoto, Yuichi; Ishikawa, Minoru Bioorganic and Medicinal Chemistry, 2010 , vol. 18, # 3 p. 1194 - 1203

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Citation Number: 27

Abstract

The physiological role of aryl hydrocarbon receptor (AhR) is not yet fully understood, and investigation is hampered by the limited solubility of reported AhR ligands in aqueous media. To achieve improved solubility, we focused on our previous finding that planarity- disruption of molecules leads to less efficient crystal packing and greater aqueous solubility. Here, we describe chemical modification of an AhR agonist, β-naphthoflavone, focusing ...