title: Fluorescent analogues of the insect neuropeptide helicokinin I: synthesis, photophysical characterization and biological activity.
abstract: In insects numerous physiological processes are regulated by neuropeptides. Two fluorescent analogues of the amino acids tryptophan and tyrosine were synthesized and incorporated in the diuretic neuropeptide helicokinin I from the moth Heliothis zea. By fluorescence emission measurements it was shown that both fluorescent helicokinin I analogues react sensitive on the dielectricity of their microenvironment. A helicokinin I analogue containing the fluorescent tryptophan mimic beta-[6'-(N,N-dimethyl)-amino-2'-naphthoyl]alanine (Ald) was shown to bind to dodecylphosphocholine (DPC) micelles by the Ald residue. A membrane binding model for helicokinin I is proposed based on data from related mammalian and insect-neuropeptides.
authors.affiliation: Fachgruppe Chemie, Bergische Universität Wuppertal, D-42119 Wuppertal, Germany.
authors.forename: Heru
authors.initials: H
authors.lastname: Chen
authors.forename: Jürgen
authors.initials: J
authors.lastname: Scherkenbeck
authors.forename: Tino
authors.initials: T
authors.lastname: Zdobinsky
authors.forename: Horst
authors.initials: H
authors.lastname: Antonicek
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives / Q000378:metabolism; D000595:Amino Acid Sequence; D000818:Animals; D005456:Fluorescent Dyes / Q000737:chemistry* / Q000378:metabolism; D007301:Insect Hormones / Q000096:biosynthesis / Q000737:chemistry* / Q000235:genetics; D019476:Insect Proteins / Q000096:biosynthesis / Q000737:chemistry* / Q000235:genetics; D008958:Models, Molecular; D009036:Moths / Q000235:genetics*; D009479:Neuropeptides / Q000096:biosynthesis / Q000737:chemistry* / Q000235:genetics; D018000:Receptors, Peptide / Q000235:genetics; D013050:Spectrometry, Fluorescence; D014364:Tryptophan / Q000031:analogs & derivatives / Q000378:metabolism; D014443:Tyrosine / Q000031:analogs & derivatives / Q000378:metabolism
chemical_list: D005456:Fluorescent Dyes; D007301:Insect Hormones; D019476:Insect Proteins; D009479:Neuropeptides; D018000:Receptors, Peptide; D014443:Tyrosine; D014364:Tryptophan; D000409:Alanine