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

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-C...

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Published inBioorganic & 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
LanguageEnglish
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
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Abstract 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.
AbstractList 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.
The aim of the present study was to describe the synthesis of a trimethyl cyclohexenonic long chain fatty alcohol (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 suggests that t-CFA n = 15 stimulates neuropeptide secretion through a calcium-dependent exocytosis mechanism.
Author Loeffler, Jean-Philippe
Luu, Bang
Gonzalez de Aguilar, José-Luis
Girlanda-Junges, Céline
Lutz-Bucher, Bernadette
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CitedBy_id crossref_primary_10_1111_j_1471_4159_2004_02601_x
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Cites_doi 10.1113/jphysiol.1993.sp019775
10.1055/s-1986-31818
10.1016/S0040-4020(98)00406-2
10.1016/0014-5793(87)81531-4
10.1016/S0040-4039(00)71334-7
10.1159/000122666
10.1021/jo01353a603
10.1016/0040-4039(96)00586-2
10.1006/frne.1995.1009
10.1016/0301-0082(90)90017-B
10.1246/cl.1975.479
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Issue 22
Keywords Rodentia
In vitro
Neuropeptide
Biological activity
Vasopressin
Primary alcohol
Vertebrata
Mammalia
Side chain
Fatty alcohol
Mouse
Animal
Chemical synthesis
Enone
Monocyclic compound
Release
Neurohypophysis
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Snippet 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...
The aim of the present study was to describe the synthesis of a trimethyl cyclohexenonic long chain fatty alcohol (t-CFA), and analyze its biological activity....
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SubjectTerms 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
Title 3-(15-Hydroxypentadecyl)-2,4,4-trimethyl-2-cyclohexen-1-one and its effect on neuropeptide secretion
URI https://dx.doi.org/10.1016/S0960-894X(00)00508-4
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