title: [Cyclic analogs of substance P. III. Cyclo (6(sup)gamma----oligomethylenediamine----11) substance P(6-11)-hexapeptides].
abstract: Cyclic analogues of substance P of the formula cyclo-[Glu-Phe-Phe-Gly-Leu-Met-NH(CH2)nNH-], where n = 3-10, 12, and open-chain analogues (XVIIIa, b) H-Glu.(NHR)-Phe-Phe-Gly-Leu-Met-NHR, where R = -CH3, -CH2CH2CH3, were synthesized. By NMR spectroscopy it was found that cyclo-compounds with n = 3-8 have regularly arranged structures, stabilized by intramolecular hydrogen bonds. Substances of this type showed less than or equal to 0.1% of the substance P activity on the guinea pig ileum, but some of them antagonize the natural peptide (for compound with n = 5 IC50 = 3.2.10(-6) M). The open-chain compounds proved to have rather high myotropic activity, viz., 22% (R = -CH3) and 8% (R = -CH2CH2CH3) of the substance P activity.
authors.forename: F K
authors.initials: FK
authors.lastname: Mutulis
authors.forename: I E
authors.initials: IE
authors.lastname: Mutule
authors.forename: G Kh
authors.initials: GKh
authors.lastname: Maurops
authors.forename: Iu
authors.initials: Iu
authors.lastname: Bergmann
authors.forename: N V
authors.initials: NV
authors.lastname: Myshliakova
authors.forename: G M
authors.initials: GM
authors.lastname: Strazda
authors.forename: E E
authors.initials: EE
authors.lastname: Liepin'sh
authors.forename: Iu B
authors.initials: IuB
authors.lastname: Saulitis
authors.forename: V D
authors.initials: VD
authors.lastname: Grigor'eva
authors.forename: Iu Iu
authors.initials: IuIu
authors.lastname: Balodis
mesh_terms: D000818:Animals; D006168:Guinea Pigs; D007082:Ileum / Q000187:drug effects; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000494:pharmacology; D011487:Protein Conformation; D013373:Substance P / Q000031:analogs & derivatives* / Q000037:antagonists & inhibitors
chemical_list: D010456:Peptides, Cyclic; D013373:Substance P
vernacular_title: Tsiklicheskie analogi veshchestva P. III. Cyclo(6(sup)gamma----oligometilendiamin----11) veshchestvo P(6-11)-geksapeptidy.