C-Methylated Analogs of Spermine and Spermidine: Synthesis and Biological Activity

• Published in: Russian journal of bioorganic chemistry Vol. 45; no. 6; pp. 463 - 487
• Main Authors: Khomutov, M. A., Mikhura, I. V., Kochetkov, S. N., Khomutov, A. R.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01-11-2019; Springer Nature B.V
• Subjects: Analogs; Biochemistry; Biological activity; Biomedical and Life Sciences; Biomedicine; Bioorganic Chemistry; Life Sciences; Organic Chemistry; Polyamines; Review Article; synthesis; spermidine; cells; spermine; methylated analogs; polyamine metabolism enzymes; polyamines
• ISSN: 1068-1620; 1608-330X
• DOI: 10.1134/S1068162019060207

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Biogenic polyamines spermine and spermidine are present in eukaryotic cells in micro- and millimolar concentrations, that determines the multiplicity of their functions and the necessity to support normal cell growth. Analogs and derivatives of spermine and spermidine are widely used in biochemistry of polyamines, a number of fundamentally significant results for the field were obtained with their help.
C
-methylated analogs of polyamines are unique, since among these compounds functionally active in vitro and in vivo spermidine and spermine mimetics were found. Biochemical properties of the compounds of this family can be regulated by moving the methyl group along the backbone of a polyamine and/or changing the configuration of the chiral center. The peculiarities of the interaction of
C
-methylated analogs of polyamines with the enzymes of their metabolism, the activity in the cell culture and the methods of synthesizing these compounds are discussed.