title: Macrocyclic analogues of the diuretic insect neuropeptide helicokinin I show strong receptor-binding.
abstract: Helicokinin I, a diuretic neuropeptide of the relevant cotton pest Helicoverpa zea represents a promising target for the design of insect neuropeptide mimetics. Using a ring-closing metathesis reaction, N-terminal bridged macrocyclic helicokinin I analogues with different rigidity were prepared and tested in a helicokinin receptor assay. A partially peptidomimetic helicokinin analogue, containing two structural modifications provides a deeper insight into the structural-requirements for receptor-binding.
authors.affiliation: Institute of Chemistry, VAST, 18-Hoang Quoc Viet Road, Hanoi, Viet Nam.
authors.forename: Chien
authors.initials: C
authors.lastname: Tran Van
authors.affiliation: Bayer CropScience AG, Alfred-Nobel-Straße 50, 40789 Monheim, Germany.
authors.forename: Dirk
authors.initials: D
authors.lastname: Nennstiel
authors.affiliation: Department of Chemistry, University of Wuppertal, Gaußstraße 20, 42119 Wuppertal, Germany. Electronic address: scherkenbeck@uni-wuppertal.de.
authors.forename: Jürgen
authors.initials: J
authors.lastname: Scherkenbeck
mesh_terms: D000595:Amino Acid Sequence; D000818:Animals; D001665:Binding Sites; D001681:Biological Assay; D004232:Diuretics / Q000138:chemical synthesis* / Q000494:pharmacology; D019476:Insect Proteins / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000378:metabolism; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D008969:Molecular Sequence Data; D009036:Moths; D009479:Neuropeptides / Q000737:chemistry* / Q000378:metabolism; D057786:Peptidomimetics / Q000138:chemical synthesis* / Q000494:pharmacology; D011485:Protein Binding / Q000187:drug effects; D011956:Receptors, Cell Surface / Q000037:antagonists & inhibitors* / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D004232:Diuretics; D019476:Insect Proteins; D047028:Macrocyclic Compounds; D009479:Neuropeptides; D057786:Peptidomimetics; D011956:Receptors, Cell Surface
keywords: Cyclopeptides; Helicokinin I; Insect neuropeptides; Peptidomimetics