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Chemistry – An Asian Journal

Exploring New Molecular Architectures for Anion Recognition: Synthesis and ATP Binding Properties of New Cyclam-Based Ditopic Polyammonium Receptors.

Authors

  • Jacky Pouessel,

    1. Laboratoire de Chimie, Electrochimie Moléculaires et Chimie Analytique, Université de Brest, UMR CNRS 6521, 6 Avenue Victor Le Gorgeu, 29200 Brest (France), Fax: (+33) 298-017-001
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  • Dr. Carla Bazzicalupi,

    1. Dipartimento di Chimica Ugo Schiff, Università di Firenze, Via della Lastruccia 3, 50019 Sesto Fiorentino, Firenze (Italy), Fax: (+39) 055-457-3364
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  • Prof. Andrea Bencini,

    Corresponding author
    1. Dipartimento di Chimica Ugo Schiff, Università di Firenze, Via della Lastruccia 3, 50019 Sesto Fiorentino, Firenze (Italy), Fax: (+39) 055-457-3364
    • Andrea Bencini, Dipartimento di Chimica Ugo Schiff, Università di Firenze, Via della Lastruccia 3, 50019 Sesto Fiorentino, Firenze (Italy), Fax: (+39) 055-457-3364

      Raphaël Tripier, Laboratoire de Chimie, Electrochimie Moléculaires et Chimie Analytique, Université de Brest, UMR CNRS 6521, 6 Avenue Victor Le Gorgeu, 29200 Brest (France), Fax: (+33) 298-017-001

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  • Dr. Hélène Bernard,

    1. Laboratoire de Chimie, Electrochimie Moléculaires et Chimie Analytique, Université de Brest, UMR CNRS 6521, 6 Avenue Victor Le Gorgeu, 29200 Brest (France), Fax: (+33) 298-017-001
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  • Dr. Claudia Giorgi,

    1. Dipartimento di Chimica Ugo Schiff, Università di Firenze, Via della Lastruccia 3, 50019 Sesto Fiorentino, Firenze (Italy), Fax: (+39) 055-457-3364
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  • Prof. Henri Handel,

    1. Laboratoire de Chimie, Electrochimie Moléculaires et Chimie Analytique, Université de Brest, UMR CNRS 6521, 6 Avenue Victor Le Gorgeu, 29200 Brest (France), Fax: (+33) 298-017-001
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  • Dr. Irene Matera,

    1. Dipartimento di Chimica Ugo Schiff, Università di Firenze, Via della Lastruccia 3, 50019 Sesto Fiorentino, Firenze (Italy), Fax: (+39) 055-457-3364
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  • Dr. Nathalie Le Bris,

    1. Laboratoire de Chimie, Electrochimie Moléculaires et Chimie Analytique, Université de Brest, UMR CNRS 6521, 6 Avenue Victor Le Gorgeu, 29200 Brest (France), Fax: (+33) 298-017-001
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  • Dr. Raphaël Tripier,

    Corresponding author
    1. Laboratoire de Chimie, Electrochimie Moléculaires et Chimie Analytique, Université de Brest, UMR CNRS 6521, 6 Avenue Victor Le Gorgeu, 29200 Brest (France), Fax: (+33) 298-017-001
    • Andrea Bencini, Dipartimento di Chimica Ugo Schiff, Università di Firenze, Via della Lastruccia 3, 50019 Sesto Fiorentino, Firenze (Italy), Fax: (+39) 055-457-3364

      Raphaël Tripier, Laboratoire de Chimie, Electrochimie Moléculaires et Chimie Analytique, Université de Brest, UMR CNRS 6521, 6 Avenue Victor Le Gorgeu, 29200 Brest (France), Fax: (+33) 298-017-001

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  • Prof. Barbara Valtancoli

    1. Dipartimento di Chimica Ugo Schiff, Università di Firenze, Via della Lastruccia 3, 50019 Sesto Fiorentino, Firenze (Italy), Fax: (+39) 055-457-3364
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Abstract

Synthesis and characterization of three new polyamine receptors, composed of a cyclam unit (cyclam=1,4,8,11-tetraazacyclotetradecane) linked by a 2,6-dimethylpyridinyl spacer to the linear polyamines 1,4,8,11-tetraazaundecane (), 1,4,7-triazaheptane (), and to a quaternary ammonium group (L3 py+), are reported. All receptors form highly charged polyammonium cations at neutral pH, suitable for anion recognition studies. ATP recognition was analyzed by using potentiometric, calorimetric, 1H and 31P NMR measurements in aqueous solution. All receptors form 1:1 adducts with ATP in aqueous solution, stabilized by charge–charge and hydrogen-bonding interactions between their ammonium groups and the anionic triphosphate chain of ATP. The binding ability of the three receptors for ATP increases in the order of L3 py+<<. These adducts are stabilized by largely favourable entropic contributions, probably due to the large desolvation of the host and guest species upon complexation. The sequence observed for the binding affinity is explained in terms of the different ability of the three receptors to wrap around the phosphate chain of ATP.

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