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Gleb D. Stepanov, Ulyana A. Budanova, Yurii L. Sebyakin
Amphiphilic
derivatives of l-lysil-l-methionine, differing in the length of the aliphatic
fragment in the hydrophobic block of lipodipeptides
Abstract
Abstract. The growth of antimicrobial
resistance to traditional antibiotics over the past decades requires
accelerating the pace of development of new approaches to reducing the activity
of various infectious processes. Natural and synthetic antimicrobial peptides,
as well as lipophilic low-molecular peptidomimetics are considered as promising
antibacterial agents. A scheme for obtaining and synthesizing a series of new
amphiphiles based on amino acid derivatives with L-lysine residues in the polar
block, L-methionine in the central fragment and with variations in the length
of the hydrocarbon radicals C8–C12 in the lipodipeptides
has been developed. The antibacterial activity of the synthesized samples has
been studied. They are highly effective against both gram-positive and
gram-negative bacteria. Within the series, a parabolic dependence of the
effectiveness of the antibacterial action on the length of the hydrocarbon
radical is observed. The lead compound Lys-Met-C11 with a MIC of
0.39 μg/ml has low cytotoxicity.
Key words: peptidomimetics, lipodipeptides,
cationic amphiphiles, antibacterial activity
Copyright (C) Chemistry Dept., Moscow State University, 2002
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