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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

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2004

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Vol. 78 / nr 3

423-430

EN

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.

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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

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2002

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Vol. 76 / nr 10

1425-1431

EN

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.

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New Proctolin Analogues Modified by the Novel D- or L-Phenylglycine Derivatives. Synthesis and Biological Studies

Szeszel-Fedorowicz W., Lisowski M., Rosiński G., Issberner J., Osborne R., Konopińska D.

Polish Journal of Chemistry

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2001

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Vol. 75, nr 3

411-417

EN

New analogues of insect neuromodulator proctolin (H-Arg-Tyr-Leu-Pro-Thr-OH), modified in position 2 of the peptide chain by L- or D-phenylglycine and its 4-substituted derivatives were synthesized. For modification of proctolin a series of novel L- or D-phenylglycine derivatives H-Phg(4-NO2)-OH (1), Boc-Phg(4-NO2)-OH (2), Boc- Phg(4-Me2N)-OH (3), H-Phg(4-OBzl)-OH (4), Boc-Phg(4-OBzl)-OH (5), H-D-Phg(4-NO2)-OH (6), Boc-D-Phg(4-NO2,)-OH (7), Boc-D-Phg(4-Me2N)-OH (8), were used. The following proctolin analogues were synthesized: H-Arg-Phg-Leu-Pro- Thr-OH (9), H-Arg-D-Phg-Leu-Pro-Thr-OH (10), H-Arg-Phg(4-OH)-Leu-Pro-Thr-OH (11), H-Arg-D-Phg(4-OH)-Leu-Pro-Thr-OH (12), H-Arg-Phg(4-NO2)-Leu- Pro-Thr-OH (13), H-Arg-D-Phg(4-NO2)-Leu-Pro-Thr-OH (14), H-Arg- Phg(4-NH2)-Leu-Pro-Thr-OH (15), H-Arg-D-Phg(4-NH2)-Leu-Pro-Thr-OH (16), H-Arg-Phg(4-NMe2)-Leu-Pro-Thr-OH (17), H-Arg-D-Phg(4-NMe2)-Leu-Pro-Thr-OH (18). Myotropic activity of proctolin analogues 9-18 was assayed in vitro on the semi-isolated heart of the mealworm Tenebrio molitor and on the foregut of the locust Schistocerca gregaria. All analogues showed a weak or none activity.