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Effect of hydrogen bonding and complexation with metal ions on the fluorescence of luotonin A

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Abstract

Fluorescence characteristics of a biologically active natural alkaloid, luotonin A (LuA), were studied by steady-state and time-resolved spectroscopic methods. The rate constant of the radiationless deactivation from the singlet-excited state diminished by more than one order of magnitude when the solvent polarity was changed from toluene to water. Dual emission was found in polyfluorinated alcohols of large hydrogen bond donating ability due to photoinitiated proton displacement along the hydrogen bond. In CH2Cl2, LuA produced both 1: 1 and 1: 2 hydrogen-bonded complexes with hexafluoro-2-propanol (HFIP) in the ground state. Photoexcitation of the 1: 2 complex led to protonated LuA, whose fluorescence appeared at a long wavelength. LuA served as a bidentate ligand forming 1: 1 complexes with metal ions in acetonitrile. The stability of the complexes diminished in the series of Cd2+ ]s> Zn2+ > Ag+, and upon competitive binding of water to the metal cations. The effect of chelate formation on the fluorescent properties was revealed.

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  1. Institute of Molecular Pharmacology, Research Centre for Natural Sciences, Hungarian Academy of Sciences, P.O. Box 17, 1525, Budapest, Hungary

    Zsombor Miskolczy & László Biczók

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  1. Zsombor Miskolczy
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  2. László Biczók
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Correspondence to László Biczók.

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Miskolczy, Z., Biczók, L. Effect of hydrogen bonding and complexation with metal ions on the fluorescence of luotonin A. Photochem Photobiol Sci 12, 936–943 (2013). https://doi.org/10.1039/c3pp50011j

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