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Molecular Recognition of Zwitterions: Enhanced Binding and Selective Recognition of Miltefosine by a Squaramide-Based Host

Authors

  • Carlos López,

    1. Departament de Química, Universitat de les Illes Balears, Ctra. Valldemossa, km 7.5, 07122 Palma de Mallorca, Illes Balears (Spain), Fax: (+34) 971173426
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  • Elena Sanna,

    1. Departament de Química, Universitat de les Illes Balears, Ctra. Valldemossa, km 7.5, 07122 Palma de Mallorca, Illes Balears (Spain), Fax: (+34) 971173426
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  • Lucas Carreras,

    1. Departament de Química, Universitat de les Illes Balears, Ctra. Valldemossa, km 7.5, 07122 Palma de Mallorca, Illes Balears (Spain), Fax: (+34) 971173426
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  • Manel Vega,

    1. Departament de Química, Universitat de les Illes Balears, Ctra. Valldemossa, km 7.5, 07122 Palma de Mallorca, Illes Balears (Spain), Fax: (+34) 971173426
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  • Prof. Carmen Rotger,

    1. Departament de Química, Universitat de les Illes Balears, Ctra. Valldemossa, km 7.5, 07122 Palma de Mallorca, Illes Balears (Spain), Fax: (+34) 971173426
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  • Prof. Antoni Costa

    Corresponding author
    1. Departament de Química, Universitat de les Illes Balears, Ctra. Valldemossa, km 7.5, 07122 Palma de Mallorca, Illes Balears (Spain), Fax: (+34) 971173426
    • Departament de Química, Universitat de les Illes Balears, Ctra. Valldemossa, km 7.5, 07122 Palma de Mallorca, Illes Balears (Spain), Fax: (+34) 971173426

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Abstract

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The importance of a synergic combination between electrostatic and hydrogen-bonding interactions has been demonstrated. A self-complementary amidosquarate-squaramide host for miltefosine has been disclosed. In DMSO, this rather structurally simple host exhibits high affinity and enhanced selectivity for miltefosine owing to the goal-keeping effect of the amidosquarate unit.

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