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Adenine nucleotide recognition by spiramycin and some of its aromatic derivatives

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Abstract

Association of adenine nucleotides with the macrocyclic antibiotic Spiramycin and two of its aromatic derivatives was studied by potentiometric titrations, 1H and 31P NMR spectrometry and molecular modelling. Spiramycin binds adenine nucleotides with K ≈ 103–104 M−1 and selectivity for ADP over ATP or AMP. The introduction of aromatic moieties reduces the strength of the binding but, selectivity order changes to ATP > ADP > AMP. Molecular models showed that complexes are mainly stabilized by electrostatic interactions between the protonated amino groups of the receptors and the phosphate groups of the nucleotides.

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Acknowledgments

K.I. Rivera Márquez glad CONACyT for her doctoral fellowship. We acknowledge LANEM by the use of the spectrometric instrumentation.

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Authors and Affiliations

  1. Centro de Investigaciones Químicas, IICBA, Universidad Autónoma del Estado de Morelos, Ave. Universidad 1001. Col. Chamilpa, Cuernavaca, Morelos, 62209, Mexico

    Karla Isabel Rivera-Márquez, Carolina Godoy-Alcántar, Miguel Ángel Claudio-Catalán & Felipe Medrano

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  1. Karla Isabel Rivera-Márquez
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  2. Carolina Godoy-Alcántar
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  3. Miguel Ángel Claudio-Catalán
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  4. Felipe Medrano
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Correspondence to Felipe Medrano.

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Rivera-Márquez, K.I., Godoy-Alcántar, C., Claudio-Catalán, M.Á. et al. Adenine nucleotide recognition by spiramycin and some of its aromatic derivatives. J Incl Phenom Macrocycl Chem 86, 211–219 (2016). https://doi.org/10.1007/s10847-016-0654-8

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  • DOI: https://doi.org/10.1007/s10847-016-0654-8

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