Russian Journal of Organic Chemistry

, Volume 41, Issue 8, pp 1158–1164 | Cite as

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

  • M.P. Evstigneev
  • A.O. Rozvadovskaya
  • O.V. Zubchenok
  • Yu.V. Mukhina
  • D.B. Davies
  • A.N. Veselkov
Article
Received:

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.

Keywords

Molecular Mechanic Spatial Structure Thermodynamic Parameter Water Solution Thermodynamic Model 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
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Copyright information

© MAIK "Nauka/Interperiodica" 2005

Authors and Affiliations

  • M.P. Evstigneev
    • 1
  • A.O. Rozvadovskaya
    • 2
  • O.V. Zubchenok
    • 2
  • Yu.V. Mukhina
    • 2
  • D.B. Davies
    • 1
  • A.N. Veselkov
    • 2
  1. 1.School of Biological and Chemical Sciences, Birkbeck CollegeUniversity of LondonUK
  2. 2.Sevastopol National Technical UniversitySevastopolUkraine

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