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1 2002

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New Protocolin Analogues Modified in Position 2 or 3 of the Peptide Chain and Their Myotropic Effects in Insects

Woźnica I., Rosiński G., Konopińska D.

Polish Journal of Chemistry

2002

Vol. 76 / nr 10

1425-1431

New analogues of insect neuromodulator proctolin (H-Arg-Tyr-Leu-Pro-Thr-OH) modified in position 2 and 3 of the peptide chain by natural or non-natural amino acid residues were synthesized. For modification of proctolin at position 2 a series of novel L-homophenylalanine derivatives H-Hpa(4-NO2)-OH (1), Boc-Hpa(4-NO2)-OH (2), Boc-Hpa(4-NH2)-OH (3), Boc-Hpa(4-NH-Z)-OH (4), Boc-Phg(4-Me2N)-OH (5) were obtained. The following two groups of proctolin analogues modified at positions 2 and 3such as: 1/ H-Arg-X2-Leu-Pro-Thr-OH, where X2 = Hpa (6), Hpa(4-NO2) (7), Hpa(4-NH2) (8), and Hpa(4-N-Me2) (9), and 2/ H-Arg-Tyr-X3-Pro-Thr-OH, where X3 = Ile (10), Phe (11), Arg (12), Sar (13), Nva (14), Nle (15), Asn (16), Asp (17), Gln (18), Glu (19), Lys (20), and _-Abu (21), were synthesized. Myotropic activity of proctolin analogues (6-21) was assayed in vitro on the semi-isolated heart of the yellow mealworm Tenebrio molitor. Analogues 10-12 and 20 retained more that 60% of proctolin activity. Other analogues showed a weak or none activity.