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Interactions of human serum albumin with bioactive 3H-imidazo[4,5-a]acridines: Insights from fluorescence spectroscopic studies

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Abstract

Several 3H-imidazo[4,5-a]acridine derivatives were conveniently synthesized by the reaction of imidazo[4,5-a]acridones in boiling POCl3. The imidazoacridones were obtained by rearrangement of 3H-imidazo[4',5':3,4]benzo[c]isoxazoles in concentrated sulfuric acid containing nitrous acid at room temperature. The structures of all newly synthesized compounds were confirmed by IR, 1H NMR, and mass spectral data. The interactions of 3H-imidazo[4,5-a]acridines with human serum albumin (HSA) were studied by fluorescence spectroscopy. The binding of 3H-imidazo[4,5-a]acridines quenches the HSA fluorescence, revealing a 1: 1 interaction with a binding constant of about 2.34 × 105–3.16 × 106 M–1. A decrease in fluorescence intensity at 339 nm, when excited at 280 nm, is attributed to changes in the environment of the protein fluorophores caused by the presence of the ligand. The differences in interactions of 3H-imidazo[4,5-a]acridines with HSA were observed using spectrofluorimetry technique.

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Authors and Affiliations

  1. Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran

    Maryam Rahbari & Mehdi Pordel

  2. Department of Biochemistry and Biophysics, Faculty of Sciences, Mashhad Branch, Islamic Azad University, Mashhad, Iran

    Jamshidkhan Chamani

Authors
  1. Maryam Rahbari
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  2. Mehdi Pordel
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  3. Jamshidkhan Chamani
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Correspondence to Mehdi Pordel.

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Rahbari, M., Pordel, M. & Chamani, J. Interactions of human serum albumin with bioactive 3H-imidazo[4,5-a]acridines: Insights from fluorescence spectroscopic studies. Russ J Bioorg Chem 42, 36–41 (2016). https://doi.org/10.1134/S1068162016010131

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  • DOI: https://doi.org/10.1134/S1068162016010131

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