Collect. Czech. Chem. Commun. 1993, 58, 918-924

Synthesis and Structure-Activity Relationship of Scyliorhinin I Analogues Modified in Position 3, 6, 7 and 8

Jolanta Zboinskaa, Krzysztof Rolkaa, Gotfryd Kupryszewskia, Krzysztof Golbab, Piotr Imiolekb, Piotr Janasb and Zbigniew S. Hermanb

a Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, PL-80-952 Gdansk, Poland
b Department of Clinical Pharmacology, Silesian Academy of Medicine, Medykow 18, Pl-40-752 Katowice, Poland


Seven analogues of scyliorhinin I modified in positions 3, 6, 7 and 8 were synthesized by the solid-phase method. Their agonistic activity was determined on isolated guinea pig ileum (GPI). Except for the two analogues modified in position 6, all exhibited dose-dependent activity. Analogues with Phe, D-Phe(F) in position 7 and Abu in position 8 appeared significantly more active than scyliorhinin I and substance P, whereas the analogue with NMeLeu in position 8 appeared to be twice as active as the native molecule, but displayed only 12% of the substance P activity. CD studies indicated that the analogues modified in position 8 behaved differently in the surroundings that mimics the biological membranes.