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1 2004

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Proctolin Analogues Modified at Position 4 of the Peptide Chain. Synthesis and Myotropic Effects in Insects

Woźnica I., Rosiński G., Konopińska D.

Polish Journal of Chemistry

2004

Vol. 78 / nr 3

423-430

The object of these investigations was synthesis and biological evaluation of new analogues of proctolin (H-Arg-Tyr-Leu-Pro-Thr-OH) modified at position 4 of the peptide chain by natural or non-natural amino acid residues, such as: Phe (1), D-Phe (2), Phg (3), D-Phg (4), N-Me-Ala (5), N-Me-Val (6), N-Me-Leu (7), Tyr (8), Arg (9), Lys (10), Nva (11), Acp (12), Ser (13), _-Abu (14), and _3,4-Pro (15). Synthesis was performed by classical solid-phase method. Myotropic activity of proctolin analogues was assayed in vitro on the semi-isolated heart of the yellow mealworm Tenebrio molitor. Analogues 1,9, and 14 retained about 50% of proctolin activity. Other analogues showed about 20% activity or were inactive. The importance of the hydrophobic amino acid residues at position 4 for the myotropic activity of proctolin was inferred.