Abstract
A series of linear and cyclic peptidomimetics composed of a cell-penetrating peptide and a non-natural, bifunctional 2,5-diketopiperazine scaffold is reported. Conformational studies revealed well-defined helical structures in micellar medium for linear structures, while cyclic peptidomimetics were more flexible. Biological investigations showed higher membrane-activity of cyclic derivatives allowing their use as shuttles for anti-cancer drugs.
Highlights
A series of linear and cyclic peptidomimetics composed of a cellpenetrating peptide and a non-natural, bifunctional 2,5-diketopiperazine scaffold is reported
The potential use of peptides as therapeutics has gained significant attention in the last decades, and research about the critical factors that favor the biological activity of naturally occurring peptides has been crucial to ease the design of new synthetic analogues.[1,2,3,4,5]
Occurring cyclic peptides have been actively investigated as potential sources of new drugs and antibiotics.[7,8,9,10,11,12,13,14]. They are resistant to proteolytic degradation when compared with linear peptide chains, and are, reliable templates for the design and biological modulation of new peptide therapeutics, including peptide carriers, such as cell-penetrating peptides (CPPs)
Summary
A series of linear and cyclic peptidomimetics composed of a cellpenetrating peptide and a non-natural, bifunctional 2,5-diketopiperazine scaffold is reported. Cell-penetrating peptides containing 2,5-diketopiperazine (DKP) scaffolds as shuttles for anti-cancer drugs: conformational studies and biological activity† We have synthesized a novel series of linear and cyclic sC18* peptide derivatives including different diastereomers of a bifunctional 2,5-diketopiperazine (DKP) within the sequence (Table 1).
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