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Heteroassociation of Caffeine with the Antibiotic Actinocyl- bis(3-dimethylaminopropylamine) in Aqueous Solution: 1H NMR Analysis

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Abstract

The heteroassociation of caffeine (CAF) and the synthetic antibiotic actinocyl-bis(3-dimethylaminopropylamine) (ACT) was studied in aqueous solution by one- and two-dimensional 1H NMR spectroscopy at 500 MHz. The equilibrium reaction constants, thermodynamic parameters (ΔH and ΔS) of ACT heteroassociation with CAF, the limiting values of proton chemical shifts of their molecules in the heteroassociation complex, and the spatial structure of the ACT–CAF complex were determined from the experimental dependences of proton chemical shifts of the aromatic molecules on concentration and temperature. The parameters of CAF heteroassociation with the phenoxazone antibiotic actinomycin D and its synthetic analogue ACT were comparatively analyzed and conclusions were made on the crucial role of stacking interactions of the chromophores of CAF and the phenoxazone antibiotics in the formation of the heterocomplexes in aqueous solution.

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Authors and Affiliations

  1. Department of Physics, Sevastopol State Technical University, Streletskaya balka, Sevastopol, Crimea, 99053, Ukraine

    A. N. Veselkov & A. O. Lantushenko

  2. School of Biological and Chemical Sciences, Birkbeck College, University of London, Gordon House, 29 Gordon Square, London WC1H OPP

    D. A. Veselkov & D. B. Davies

Authors
  1. A. N. Veselkov
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  2. A. O. Lantushenko
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  3. D. A. Veselkov
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  4. D. B. Davies
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Correspondence to A. N. Veselkov.

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Veselkov, A.N., Lantushenko, A.O., Veselkov, D.A. et al. Heteroassociation of Caffeine with the Antibiotic Actinocyl- bis(3-dimethylaminopropylamine) in Aqueous Solution: 1H NMR Analysis. Russian Journal of Bioorganic Chemistry 28, 430–436 (2002). https://doi.org/10.1023/A:1020480313814

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