Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Binding Geometry of Inclusion Complex as a Determinant Factor for Aqueous Solubility of the Flavonoid/β-Cyclodextrin Complexes Based on Molecular Dynamics Simulations

  • Choi, Young-Jin (Department of Microbial Engineering, Bio/Molecular Informatics Center, Konkuk University) ;
  • Lee, Jong-Hyun (College of Information and Communication, Konkuk University) ;
  • Cho, Kum-Won (Korea Institute of Science and Technology Information) ;
  • Hwang, Sun-Tae (Department of Computer Science, Kookmin University) ;
  • Jeong, Karp-Joo (College of Information and Communication, Konkuk University) ;
  • Jung, Seun-Ho (Department of Microbial Engineering Bio/Molecular Informatics Center, Konkuk University)
  • Published : 2005.08.20
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Abstract

A computational study based on molecular dynamics (MD) simulations was performed in order to explain the difference in aqueous solubilities of two flavonoid/$\beta$-cyclodextrin ($\beta$-CD) complexes, hesperetin/$\beta$-CD and naringenin/$\beta$-CD. The aqueous solubility of each flavonoid/$\beta$-CD complex could be characterized by complexwater interaction not by flavonoid-CD interaction. The radial distribution of water around each inclusion complex elucidated the difference of an experimentally observed solubility of each flavonoid/$\beta$-CD complex. The analyzed results suggested that a bulky hydrophobic moiety (-$OCH_3$) of B-ring of hesperetin nearby primary rim of $\beta$-CD was responsible for lower aqueous solubility of the hesperetin/$\beta$-CD complex.

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