engleski

Novel side-chain glucosylated and adamantylated [Asp2/Glu2]enkephalin analogues: synthesis and in vitro growth inhibition of human tumor cells

A series of new backbone-modified Leu- and Met-enkephalin analogues (13-20 a and b) were synthesized. Backbone manipulations involved the replacement of the Gly2 residue in Tyr-Gly-Gly-Phe-Leu/Met with side-chain glucosylated or adamantylated D/L-aspartic or -glutamic acids. The in vitro antiproliferative activity of these compounds was evaluated for several cell lines and the results were compared with the effect of Met-enkephalin, the native opioid growth factor (OGF). The tested compounds modestly inhibited the growth of the tumor cells (20-50% inhibition at millimolar concentrations). Among the tested compounds, Tyr-D-Glu(AdNH)-Gly-Phe-Met (20b) showed significant antiproliferative activity, somewhat more pronounced on MCF-7 (breast carcinoma) and MOLT-4 (lymphoblastic leukemia) cells.

Leu-enkephalin ; Met-enkephalin ; Opioid peptides ; In vitro antiproliferative activity ; Peptide synthesis ; Analogues

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