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Synthesis, conformation and biological activity of linear and cyclic Thr6-bradykinin analogues containing N-benzylglycine in place of phenylalanine

✍ Scribed by L. Biondi; F. Filira; M. Gobbo; B. Scolaro; R. Rocchi; R. Galeazzi; M. Orena; A. Zeegers; T. Piek

Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
181 KB
Volume
7
Category
Article
ISSN
1075-2617

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✦ Synopsis

Abstract

Three linear Thr^6^‐bradykinin analogues in which either one or both the two phenylalanine residues in the peptide sequence have been substituted by N‐benzylglycine (BzlGly) and their head‐to‐tail cyclic analogues were synthesized and tested on an isolated rat duodenum preparation. The linear (BzlGly^5^,Thr^6^‐BK, BzlGly^8^,Thr^6^‐BK and BzlGly^5,8^,Thr^6^‐BK) and the cyclic (cyclo BzlGly^5^,Thr^6^‐BK, cyclo BzlGly^8^,Thr^6^‐BK and cyclo BzlGly^5,8^,Thr^6^‐BK) peptoid‐like analogues were characterized by amino acid analysis, optical rotation, analytical HPLC and MALDI‐TOF mass spectroscopy. The conformational features of both the linear and cyclic derivatives were investigated by FT‐IR and CD measurements. Preliminary molecular mechanics calculations were also performed on some synthetic peptides. Pharmacological screening using the relaxation of the isolated rat duodenum preparation showed that incorporation of N‐benzylglycine at positions 5 and/or 8 in the linear Thr^6^‐BK causes a substantial decrease in potency. Comparable incorporation in cyclo Thr^6^‐BK, at position 8, or 5 and 8, resulted in nearly inactive analogues. However, cyclo BzlGly^5^,Thr^6^‐BK showed a potency which is of the same order of magnitude as for cyclo‐BK and cyclo Thr^6^‐BK. Copyright © 2001 European Peptide Society and John Wiley & Sons, Ltd.

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