title: Lipophilic peptides: synthesis of lauroyl thyrotropin-releasing hormone and its biological activity.
abstract: Thyrotropin-releasing hormone (TRH) was derivatized by chemical attachment of lauric acid to the N-terminal pyroglutamyl group. The product was confirmed to be more lipophilic than TRH by high-performance liquid chromatography and measurement of partition coefficients. The central nervous system activity and endocrine activity of the lauroyl derivative were only slightly reduced, to 81 and 64% of the parent TRH, respectively. Lipophilic derivatization may be generally applicable to transmembrane delivery of peptides.
authors.affiliation: Department of Biopharmaceutics, Kyoto Pharmaceutical University, Japan.
authors.forename: S
authors.initials: S
authors.lastname: Muranishi
authors.forename: A
authors.initials: A
authors.lastname: Sakai
authors.forename: K
authors.initials: K
authors.lastname: Yamada
authors.forename: M
authors.initials: M
authors.lastname: Murakami
authors.forename: K
authors.initials: K
authors.lastname: Takada
authors.forename: Y
authors.initials: Y
authors.lastname: Kiso
mesh_terms: D000595:Amino Acid Sequence; D000818:Animals; D008297:Male; D051379:Mice; D008813:Mice, Inbred ICR; D008969:Molecular Sequence Data; D051381:Rats; D011919:Rats, Inbred Strains; D012890:Sleep / Q000187:drug effects; D013972:Thyrotropin / Q000378:metabolism; D013973:Thyrotropin-Releasing Hormone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D013973:Thyrotropin-Releasing Hormone; D013972:Thyrotropin