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Analysis by Means of 1H NMR Spectroscopy of Heteroassociaion in Water Solution of Antitumor Antibiotics Daunomycin and Actinomycin D

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Abstract

Heteroassociation of aromatic antitumor antibiotics daunomycin (DAU) and actinomycin D (AMD) was investigated using 1D and 2D 1H NMR spectroscopy (at 500 MHz) and molecular mechanics procedure with the goal of establishing the mechanism of the combined action of antibiotics in the system AMD-DAU. The experimental data were processed applying a modified statistical and thermodynamic model of the molecules heteroassociation. Proceeding from this model the values were obtained of induced proton chemical shifts, equilibrium constant and thermodynamic parameters of complexing reaction between DAU and AMD. By means of molecular mechanics with the use of X-PLOR software and of the analysis results of the induced proton chemical shifts in the molecules the most probable spatial structure, 1:1, was established for the heterocomplex of DAU and AMD. Heterocomplexes of daunomycin and actinomycin D form due to stacking interaction between the aromatic chromophores with possible additional stabilization of the complexes by an intermolecular hydrogen bond.

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Authors and Affiliations

  1. School of Biological and Chemical Sciences, Birkbeck College, University of London, UK

    M.P. Evstigneev & D.B. Davies

  2. Sevastopol National Technical University, Sevastopol, 99053, Ukraine

    A.O. Rozvadovskaya, O.V. Zubchenok, Yu.V. Mukhina & A.N. Veselkov

Authors
  1. M.P. Evstigneev
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  2. A.O. Rozvadovskaya
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  3. O.V. Zubchenok
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  4. Yu.V. Mukhina
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  5. D.B. Davies
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  6. A.N. Veselkov
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__________

Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 8, 2005, pp. 1180–1186.

Original Russian Text Copyright © 2005 by Evstigneev, Rozvadovskaya, Zubchenok, Mukhina, Davies, Veselkov.

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Evstigneev, M., Rozvadovskaya, A., Zubchenok, O. et al. Analysis by Means of 1H NMR Spectroscopy of Heteroassociaion in Water Solution of Antitumor Antibiotics Daunomycin and Actinomycin D. Russ J Org Chem 41, 1158–1164 (2005). https://doi.org/10.1007/s11178-005-0308-6

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  • DOI: https://doi.org/10.1007/s11178-005-0308-6

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