MilliporeSigma
  • Home
  • Search Results
  • beta-Naphthoflavone analogs as potent and soluble aryl hydrocarbon receptor agonists: improvement of solubility by disruption of molecular planarity.

beta-Naphthoflavone analogs as potent and soluble aryl hydrocarbon receptor agonists: improvement of solubility by disruption of molecular planarity.

Bioorganic & medicinal chemistry (2010-01-12)
Yuji Fujita, Mitsuhiro Yonehara, Masashi Tetsuhashi, Tomomi Noguchi-Yachide, Yuichi Hashimoto, Minoru Ishikawa
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, beta-naphthoflavone, focusing on planarity-disruption. As expected, introduction of substituents at the ortho-positions of the phenyl group resulted in greater solubility. Among the compounds prepared, the fluoro analog showed more potent AhR agonistic activity and greater solubility than did beta-naphthoflavone. Our results indicate that this strategy to improve aqueous solubility, that is, introduction of substituent(s) that disrupt planarity, may be generally applicable to bicyclic molecules.

MATERIALS
Product Number
Brand
Product Description

Supelco
Benzo[a]pyrene solution, 100 μg/mL in cyclohexane, analytical standard
Sigma-Aldrich
β-Naphthoflavone, ≥98%
Sigma-Aldrich
Benzo[a]pyrene, ≥96% (HPLC)
Supelco
Benzo[a]pyrene, certified reference material, TraceCERT®
Sigma-Aldrich
Indigo, synthetic, Dye content 95 %
Supelco
Benzo[a]pyrene, analytical standard, for environmental analysis