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We incorporated \ud835\udcb9\u2010Tic and octahydroindole\u20102\u2010carboxylic acid (Oic) residues (present in known active antagonists) in a cyclic pentapeptide that would place the \ud835\udcb9\u2010aa in the <jats:italic>i<\/jats:italic>+l position of the \u03b2\u2010turn and a proline as a bridge between the <jats:italic>C<\/jats:italic>\u2010 and <jats:italic>N<\/jats:italic>\u2010termini sides of the turn. In positions <jats:italic>i<\/jats:italic> and <jats:italic>i<\/jats:italic>+3 alkyl, aromatic, polar or charged amino acids could be introduced without dramatically changing the overall structure. Ten analogues were studied using <jats:sup>1<\/jats:sup>H nuclear magnetic resonance (NMR) and evaluated for their binding affinity for the human B<jats:sub>2<\/jats:sub> receptor. The NMR data in dimethylsulfoxide (DMSO) confirmed the structural homogeneity within the class and, on the basis of this, one representative member of the series was chosen for a detailed structure determination using NMR data in sodium dodecylsulphate (SDS) micelles and molecular dynamics calculations. Despite the structural similarity, the binding affinity of the ten analogues was strongly influenced by the nature of the side\u2010chains in positions <jats:italic>i<\/jats:italic> and <jats:italic>i<\/jats:italic>+3, with the doubly charged analogue <jats:bold>49<\/jats:bold> (p<jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub>=6.2) proving best. This compound may serve as the starting point for the discovery of new non\u2010peptide bradykinin B<jats:sub>2<\/jats:sub> receptor antagonists. Copyright \u00a9 2001 European Peptide Society and John Wiley &amp; Sons, Ltd.<\/jats:p>","DOI":"10.1002\/psc.321","type":"journal-article","created":{"date-parts":[[2005,1,26]],"date-time":"2005-01-26T06:11:52Z","timestamp":1106719912000},"page":"270-283","update-policy":"http:\/\/dx.doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["New conformationally homogeneous \u03b2\u2010turn antagonists of the human B<sub>2<\/sub> kinin receptor"],"prefix":"10.1002","volume":"7","author":[{"given":"Edith S.","family":"Monteagudo","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Federico","family":"Calvani","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Fernando","family":"Catrambone","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Christopher I.","family":"Fincham","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andrea","family":"Madami","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Stefania","family":"Meini","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rosa","family":"Terracciano","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2001,5]]},"reference":[{"key":"e_1_2_1_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/0163-7258(92)90016-S"},{"key":"e_1_2_1_3_2","doi-asserted-by":"publisher","DOI":"10.1161\/01.HYP.26.2.221"},{"key":"e_1_2_1_4_2","doi-asserted-by":"publisher","DOI":"10.1097\/00005344-199015061-00005"},{"key":"e_1_2_1_5_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.2042-7158.1980.tb12833.x"},{"key":"e_1_2_1_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/0006-291X(92)90445-Q"},{"key":"e_1_2_1_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(17)31844-6"},{"key":"e_1_2_1_8_2","first-page":"357","article-title":"The B1 receptors for kinins","volume":"50","author":"Marceau F","year":"1998","journal-title":"Pharmacol. 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