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PubMed1975

Radioprotection of whole-body gamma irradiation induced alterations in lipid metabolism of liver and plasma by AET (S-2, aminoethyl isothiuronium Br. H. Br.) and serotonin in rats.

Radioprotective effect of AET, serotonin and their mixture has been studied on liver and plasma lipid metabolism 24 hrs and 48 hrs after irradiation in fasted male rats. AET and serotonin both gave significant radioprotection to certain liver and plasma lipid components, but the mixture of the two afforded a better protection. The non-radioprotection of plasma NEFA, phospholipids and phosphatidyl choline levels by serotonin observed in irradiated rats was because serotonin itself raised the levels of these lipids in control rats. Serotonin alone or in mixture effectively protected the radiation-induced increased incorporation of NaH2(32)PO4 into liver phospholipids. Mixture of AET and serotonin failed to protect the increased incorporation of aceae-1-14-C into liver total fatty acids and cholesterol, but it prevented this increased incorporation into liver triglycerides and phospholipids.

Acetates↗
PubMedDate not supplied

Controlled template-assisted assembly of plasmid DNA into nanometric particles with high DNA concentration.

A series of novel cationic detergents that contain cleavable hydrophilic isothiuronium headgroups was synthesized, and their utility in controlled assembly of plasmid DNA into small stable particles with high DNA concentration investigated. The detergents have alkyl chains of C(8)-C(12) and contain hydrophilic isothiuronium headgroups that give relatively high critical micelle concentration (CMC) to the detergents (>10 mM). The isothiuronium group masks a sulfhydryl group on the detergent and can be cleaved in a controlled manner under basic conditions to generate a reactive thiol group. The thiol group can undergo a further reaction after the detergents have accumulated on a DNA template to form a disulfide-linked lipid containing two alkyl chains. The pH-dependent kinetics of cleavage of the isothiuronium group, the CMC of the surfactants, the formation of the complexes, and the transfection efficiency of the DNA complexes have been investigated. Using the C(12) detergent, a approximately 6 kilo-basepair plasmid DNA was compacted into a small particle with an average diameter of around 40 nm with a approximately -13 mV zeta-potential at high DNA concentration (up to 0.3 mg/mL). The compounds were well tolerated in cell culture and showed no cytotoxicity under their CMCs. Under appropriate conditions, the small particle retained transfection activity.

Animals↗
PubMed1981

Levamisole and other diamine oxidase inhibitors as inhibitors of sperm motility.

Levamisole, an anthelmintic drug and inhibitor of sperm motility, is a potent inhibitor of seminal diamine oxidase. Many other diamine oxidase inhibitors also inhibit sperm motility. The most active class of these sperm motility inhibitors is the group for isothiuronium compounds, some of which are much more potent than many other metabolic inhibitors tested. They also possess the property of inducing sperm to be motile in closed circles becoming immotile with a characteristically curled shape, and are active against mouse epididymal, rabbit, and human spermatozoa.

Amine Oxidase (Copper-Containing)↗
PubMed1995

Diamine and triamine analogs and derivatives as inhibitors of deoxyhypusine synthase: synthesis and biological activity.

Deoxyhypusine synthase catalyzes the initial step in the posttranslational formation of the amino acid hypusine [N epsilon-(4-amino-2-hydroxybutyl)lysine] in eukaryotic initiation factor 5A (eIF-5A). eIF-5A and its hypusine modification are believed to be essential for cell growth. A number of compounds related to diamines and triamines were synthesized and tested as inhibitors of this enzyme. The findings indicate that the long chain triamines 2a and 2b and their guanyl derivatives 3a, 3b, 4a, and 4b exert inhibition by binding to enzyme through only a portion of their structures at any one time. The inhibition exhibited by N-ethyl-1,7-diaminoheptane 20 and its guanyl derivative 21 supports this notion and is evidence for participation of the secondary amino group in binding to enzyme. There is preliminary evidence that amidino and isothiuronium groups may also serve as basic centers for binding to enzyme. Few of the compounds tested here were comparable in inhibitory potency to 1-guanidino-7-aminoheptane (GC7) the most effective known inhibitor of deoxhypusine synthase, and none proved nearly as efficient as GC7 in inhibiting the enzyme in Chinese hamster ovary cells. Hence, unlike the antiproliferative effect of GC7, for which there is evidence of cause by interference with deoxhypusine synthase catalysis (Park, M. H.; Wolff, E. C.; Lee, Y. B.; Folk, J. E. J. Biol. Chem. 269, 1994, 27827-27832), the effective growth arrest exerted by several of the newly synthesized compounds cannot be attributed to inhibition of hypusine synthesis.

Animals↗
PubMed1971

Synthesis and oxidation of aminoalkyl-onium compounds by pig kidney diamine oxidase.

1. The preparation of a series of compounds derived from diamines by replacing one amino group by a dimethylsulphonium, isothiuronium, trimethylammonium, NN'-dimethylimidazolium or N-methylpyridinium species is described. 2. The behaviour of these compounds as substrates of pig kidney diamine oxidase is reported. All but the trimethylammonium compounds proved to be substrates. 3. Many of these compounds showed potent inhibition at high substrate concentration and this was studied. 4. On the basis of these and other observations a scheme for enzyme-substrate interaction is suggested.

Alkanes↗