A Structural and Thermodynamic Analysis of Novatrone and Flavin Mononucleotide Heteroassociation in Aqueous Solution by 1H NMR Spectroscopy

被引:0
作者
A. N. Veselkov
M. P. Evstigneev
A. O. Rozvadovska
Yu. V. Mukhina
D. B. Davies
机构
[1] Sevastopol National Technical University,School of Biological and Chemical Sciences, Birkbeck College
[2] University of London,undefined
来源
Russian Journal of Bioorganic Chemistry | 2005年 / 31卷
关键词
antitumor antibiotic; flavin mononucleotide; heteroassociation; novatrone; NMR spectroscopy;
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中图分类号
学科分类号
摘要
A heteroassociation of the antitumor antibiotic novatrone (NOV) and flavin mononucleotide (FMN) in aqueous solution was studied by one- and two-dimentional 1H NMR spectroscopy (500 MHz) to elucidate the molecular mechanism of the possible combined action of the antibiotic and the vitamin. The equilibrium reaction constants, the induced proton chemical shifts, and the thermodynamic parameters (ΔH and ΔS) of the NOV and FMN heteroassociation were determined from the concentration and temperature dependences of proton chemical shifts of the aromatic molecules. The most favorable structure of the 1 : 1 NOV-FMN complex was determined by both the method of molecular mechanics (X-PLOR software) and the induced proton chemical shifts of the molecules. An analysis of the results suggests that the NOV-FMN intermolecular complexes are mainly stabilized by stacking interactions of their aromatic chromophores. An additional stabilization is possible due to intermolecular hydrogen bonds. It was concluded that the aromatic molecules of vitamins, in particular, FMN, can form energetically favorable heterocomplexes with aromatic antitumor antibiotics in aqueous solutions, which could result in a modulation of their medical and biological action.
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页码:453 / 459
页数:6
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