Lipophilic peptides: synthesis of lauroyl thyrotropin-releasing hormone and its biological activity.
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.
Muranishi
S
S
Department of Biopharmaceutics, Kyoto Pharmaceutical University, Japan.
Sakai
A
A
Yamada
K
K
Murakami
M
M
Takada
K
K
Kiso
Y
Y
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
D013973:Thyrotropin-Releasing Hormone; D013972:Thyrotropin