3-(15-Hydroxypentadecyl)-2,4,4-trimethyl-2-cyclohexen-1-one and its effect on neuropeptide secretion

• Published in: Bioorganic & medicinal chemistry letters Vol. 10; no. 22; pp. 2537 - 2539
• Main Authors: Girlanda-Junges, Céline, Lutz-Bucher, Bernadette, Gonzalez de Aguilar, José-Luis, Loeffler, Jean-Philippe, Luu, Bang
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 20.11.2000; Elsevier
• Subjects: Animals; Arginine Vasopressin - biosynthesis; Biological and medical sciences; Cyclohexanones - chemistry; Cyclohexanones - pharmacology; Fatty Alcohols; Fundamental and applied biological sciences. Psychology; Hormones and neuropeptides. Regulation; Hypothalamus. Hypophysis. Epiphysis. Urophysis; Male; Mice; Pituitary Gland - drug effects; Pituitary Gland - metabolism; Vertebrates: endocrinology; Rodentia; In vitro; Neuropeptide; Biological activity; Vasopressin; Primary alcohol; Vertebrata; Mammalia; Side chain; Fatty alcohol; Mouse; Animal; Chemical synthesis; Enone; Monocyclic compound; Release; Neurohypophysis
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/S0960-894X(00)00508-4

The aim of the present study was to describe the synthesis of a t rimethyl c yclohexenonic long chain f atty a lcohol ( t-CFA), and analyze its biological activity. Specifically, 3-(15-hydroxypentadecyl)-2,4,4-trimethyl-2-cyclohexen-1-one, the t-CFA containing 15 carbon atoms on the side chain ( t-CFA n=15) stimulated arginine vasopressin secretion in nerve terminals of the neurohypophysis. This effect was inhibited by extracellular calcium depletion, which suggets that t-CFA n=15 stimulates neuropeptide secretion through a calcium-dependent exocytosis mechanism.