Ditopic complexation of selenite anions or calcium cations by pirenoxine: An implication for anti-cataractogenesis

Jiahn Haur Liao, Chien Sheng Chen, Chao Chien Hu, Wei Ting Chen, Shao Pin Wang, I. Lin Lin, Yi Han Huang, Ming Hsuan Tsai, Tzu Hua Wu, Fu Yung Huang, Shih Hsiung Wu

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Abstract

This study investigated whether and how pirenoxine (PRX) interacts with selenite or calcium ions, as these two ions have been proven respectively a factor leading to the formation of lens cataract. UV, NMR, and isothermal titration calorimetry (ITC) analysis indicated that PRX could bind maximum up to six selenite anions and the binding site preference was concentration dependent with the peripheral binding first followed by the π-π interactions with the aromatic moiety; while for calcium cation interaction the 3-carboxylate and β-ketoimine functional groups were responsible for chelating calcium ions. The results obtained by MP2/6-31+G(d) molecular orbital calculations provided theoretical evidence in support of the π-π interactions between selenite and the PRX aromatic framework, and further analysis of the binding energies with the aromatic moiety indicates that these interactions take place most likely at the benzoquinone (ring I) π-system. The calcium binding preferences with PRX were also determined based on the stabilization energy obtained by B3LYP/6-31+G(d) calculations, showing the binding preferences were site 2 > site 1 > site 3 > ring II, consistent with the experimental data. The in vitro study of the reduction of selenite or calcium ions-induced lens turbidity by PRX with ditopic recognition properties was thus demonstrated. These results may provide a rationale for using PRX as an anti-cataract agent and warrant further biological studies.

Original languageEnglish
Pages (from-to)365-377
Number of pages13
JournalInorganic Chemistry
Volume50
Issue number1
DOIs
Publication statusPublished - Jan 3 2011

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Physical and Theoretical Chemistry

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    Liao, J. H., Chen, C. S., Hu, C. C., Chen, W. T., Wang, S. P., Lin, I. L., Huang, Y. H., Tsai, M. H., Wu, T. H., Huang, F. Y., & Wu, S. H. (2011). Ditopic complexation of selenite anions or calcium cations by pirenoxine: An implication for anti-cataractogenesis. Inorganic Chemistry, 50(1), 365-377. https://doi.org/10.1021/ic102151p