Biomaterial Database

Insulin-like partial effects of agmatine derivatives in adipocytes. 1980

G Weitzel, and B Pfeiffer, and W Stock

In previous investigations, we described insulin-like effects of agmatine [(4-aminobutyl)guanidine] in vitro. In the present work we have examined whether these effects of agmatine can be enhanced by variation in chain length (C3 and C5 forms) and by alkylation. Propyl, butyl, pentyl, hexyl, octyl, isobutyl and isopentyl groups were introduced into C4- and C5-agmatine by hydrogenation of the corresponding azomethines. Alkylation of C3-agmatine was carried out by addition of alkylamines to acrylonitrile, followed by hydrogenation and amidination. For the biological assays, isolated fat cells from rat epididymic adipose tissue were used. N4-Butyl- and N4-pentyl-C4-agmatines lead to a two-fold, N4-hexyl-C4-agmatine to a three-fold enhancement of glucose oxidation in adipocytes. Alkylated C4- and C5-agmatines induce a three-fold increase in lipogenesis compared to agmatine. Alkylation of C3-agmatine does not increase its potency in this test. In our test system, insulin decreases adrenalin-induced lipolysis to 40% of the control value (100%). Agmatine and alkylated C4-agmatines yield very similar values (37% and 27-44% respectively). The alkylated C3-agmatines also exert strongly antilipolytic effects (25-35%), while the effects of the alkylated C5-agmatines are weaker. The synthesized agmatine derivatives were injected intraperitoneally into mice. Tolerable doses do not cause any significant reduction in blood glucose levels.

UI	MeSH Term	Description	Entries
D007328	Insulin	A 51-amino acid pancreatic hormone that plays a major role in the regulation of glucose metabolism, directly by suppressing endogenous glucose production (GLYCOGENOLYSIS; GLUCONEOGENESIS) and indirectly by suppressing GLUCAGON secretion and LIPOLYSIS. Native insulin is a globular protein comprised of a zinc-coordinated hexamer. Each insulin monomer containing two chains, A (21 residues) and B (30 residues), linked by two disulfide bonds. Insulin is used as a drug to control insulin-dependent diabetes mellitus (DIABETES MELLITUS, TYPE 1).	Iletin,Insulin A Chain,Insulin B Chain,Insulin, Regular,Novolin,Sodium Insulin,Soluble Insulin,Chain, Insulin B,Insulin, Sodium,Insulin, Soluble,Regular Insulin
D008055	Lipids	A generic term for fats and lipoids, the alcohol-ether-soluble constituents of protoplasm, which are insoluble in water. They comprise the fats, fatty oils, essential oils, waxes, phospholipids, glycolipids, sulfolipids, aminolipids, chromolipids (lipochromes), and fatty acids. (Grant & Hackh's Chemical Dictionary, 5th ed)	Lipid
D008066	Lipolysis	The metabolic process of breaking down LIPIDS to release FREE FATTY ACIDS, the major oxidative fuel for the body. Lipolysis may involve dietary lipids in the DIGESTIVE TRACT, circulating lipids in the BLOOD, and stored lipids in the ADIPOSE TISSUE or the LIVER. A number of enzymes are involved in such lipid hydrolysis, such as LIPASE and LIPOPROTEIN LIPASE from various tissues.	Lipolyses
D008297	Male		Males
D010084	Oxidation-Reduction	A chemical reaction in which an electron is transferred from one molecule to another. The electron-donating molecule is the reducing agent or reductant; the electron-accepting molecule is the oxidizing agent or oxidant. Reducing and oxidizing agents function as conjugate reductant-oxidant pairs or redox pairs (Lehninger, Principles of Biochemistry, 1982, p471).	Redox,Oxidation Reduction
D005947	Glucose	A primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. It is used therapeutically in fluid and nutrient replacement.	Dextrose,Anhydrous Dextrose,D-Glucose,Glucose Monohydrate,Glucose, (DL)-Isomer,Glucose, (alpha-D)-Isomer,Glucose, (beta-D)-Isomer,D Glucose,Dextrose, Anhydrous,Monohydrate, Glucose
D006146	Guanidines	A family of iminourea derivatives. The parent compound has been isolated from mushrooms, corn germ, rice hulls, mussels, earthworms, and turnip juice. Derivatives may have antiviral and antifungal properties.
D000273	Adipose Tissue	Specialized connective tissue composed of fat cells (ADIPOCYTES). It is the site of stored FATS, usually in the form of TRIGLYCERIDES. In mammals, there are two types of adipose tissue, the WHITE FAT and the BROWN FAT. Their relative distributions vary in different species with most adipose tissue being white.	Fatty Tissue,Body Fat,Fat Pad,Fat Pads,Pad, Fat,Pads, Fat,Tissue, Adipose,Tissue, Fatty
D000376	Agmatine	Decarboxylated arginine, isolated from several plant and animal sources, e.g., pollen, ergot, herring sperm, octopus muscle.	1-Amino-4-guanidinobutane,4-(Aminobutyl)guanidine,1 Amino 4 guanidinobutane
D000478	Alkylation	The covalent bonding of an alkyl group to an organic compound. It can occur by a simple addition reaction or by substitution of another functional group.	Alkylations