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Molecular Orbital Analysis and Quantitative Structure-Activity Relationships for the Anthracycline Antibiotics

Author:
Bushelev, S. N., Stepanov, N. F.
Source:
Zeitschrift für Naturforschung 2014 v.44 no.3-4 pp. 212-216
ISSN:
1865-7125
Subject:
DNA, anthracyclines, antibiotics, bioactive properties, energy, equations, mechanics, models, quantitative structure-activity relationships
Abstract:
Semiempirical CNDO/2 calculations of the electronic and molecular structures have been car­ried out for six antitumor anthracycline antibiotics. The strong correlation between their biological activity and such molecular properties as chromophore dipole moment, energy of frontier orbitals, and steric volum es was found and the proper QSAR equations were constructed. The molecular mechanics model showed the weak dependence the DNA-intercalation energy on differences in chromophore constituents (C4 and C9 positions). The expression for the intercala­tion energy has also been obtained on the ground of a quantum-statistical approach: it was applied to the DNA -intercalation energy calculations for the same six anthracyclines. The results agree with the molecular mechanics ones quite satisfactory.
Agid:
5228003