Redox-active ferrocene-modified pyrimidines and adenine as antitumor agents: structure, separation of enantiomers, and inhihibition of the DNA synthesis in tumor cells

The structures, electrochemical properties, enantiomeric separation of ferrocenyl-(alkyl)pyrimidines and ferrocenyl(ethyl)adenine and their effects on the DNA synthesis in tumor cells were studied. Enantiomeric mixtures were separated by HPLC on modified cellulose as the chiral selector. The electro...

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Published in:Russian chemical bulletin 2013-09, Vol.62 (9), p.2056-2064
Main Authors: Snegur, L. V., Zykova, S. I., Simenel, A. A., Nekrasov, Yu. S., Starikova, Z. A., Peregudova, S. M., Il’in, M. M., Kachala, V. V., Sviridova, I. K., Sergeeva, N. S.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
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Inorganic Chemistry
Organic Chemistry
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Summary:The structures, electrochemical properties, enantiomeric separation of ferrocenyl-(alkyl)pyrimidines and ferrocenyl(ethyl)adenine and their effects on the DNA synthesis in tumor cells were studied. Enantiomeric mixtures were separated by HPLC on modified cellulose as the chiral selector. The electrochemical properties of compounds were studied by cyclic voltammetry. All compounds have reversible single-electron redox transition in the region of 0.52–0.60 V, which belongs to ferrocene—ferrocenium with a positive shift compared to ferrocene (0.52 V). The molecular structure of 1- N -(ferrocenylbenzyl)-5-iodocytosine was studied by X-ray diffraction. 1- N -(Ferrocenylethyl)adenine was studied for ability to inhibit the DNA synthesis in the human ovarian cancer cell culture by the 3 H-thymidine test.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-013-0298-4