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PubMedDate not supplied

Effect of fedotozine on human distal colon.

Fedotozine was rested in colonic strips removed during surgery from patients suffering from different diseases of the colon; the effects were compared to those of morphine and of the selective opiate agonist U-69593. Fedotozine did not affect the spontaneous motility of human colonic strips, unless very high concentrations were used. Fedotozine (10(-6)-3 x 10(-4) M) induced a concentration-dependent reduction of the excitatory effect induced by field stimulation, an effect which was partially mimicked by compound U-69593 and by morphine but not inhibited by naloxone. The cumulative dose-response curve to exogenous acetylcholine was inhibited by fedotozine (3 x 10(-4) M), whereas morphine had no effect up to 3 x 10(-4) M. In colonic strips incubated with [3H]-choline, fedotozine (10(-5)-10(-4) M) induced an erratic decrease of acetylcholine-release induced by electric stimulation. In our experimental model, the inhibitory effect of fedotozine does not seem to be related to opioid receptor activation.

Acetylcholine↗
PubMedDate not supplied

Differential effects of organometallic tin compounds on Na+/K+-ATPase activity.

In vitro effects of six dibenzyltin dichloride (A-series) and another six dibenzyltin diisothiocyanate (B-series) complexes on Na+/K+-ATPase were studied. The rat brain synaptic membranes were prepared and significant ATPase inhibition was observed with all the complexes in a dose-dependent manner. The order of potency on Na+/K+-ATPase activity of the chloride complexes was found to be higher than that of the isothiocyanate complexes. The IC50 values range from 64 microM to 252 microM for the chloride complexes and from 132 microM to 399 microM for the isothiocyanate complexes. A structure-activity relationship could be derived for the chloride complexes.

Animals↗
PubMed1994

Technetium-99m N,N'-bis(2-mercapto-2-methylpropyl)-2-aminobenzylamine: technetium-99m complexes of a novel bis(aminoethanethiol) ligand.

A new N2S2 ligand system, N,N'-bis(2-mercapto-2-methylpropyl)-2- aminobenzylamine, U-BAT, 1, containing uneven amine groups (two amine groups with different pKa values) for complexing [TcVO]3+, was prepared. The reaction of this novel ligand with [99mTc]pertechnetate, in the presence of stannous tartrate as the reducing agent, produces the neutral and lipid-soluble [99mTc]TcVO(U-BAT), TcS2C15H23N2O, 2. However, when the same reaction was carried out at a higher pH, 9-10, and with 30 min of heating (100 degrees C), a second neutral but more lipid-soluble complex, [99mTc]TcVO(OU-BAT), TcS2C15H21N2O, 3, was isolated. The X-ray crystallography data of the 99Tc complexes show square pyramidal coordination with N2S2 as the base and the Tc = O in the apical position. Compound 3 can be derived from 2 by an oxidation of the ligand to form an imine. After iv injection into rats, the neutral and lipid-soluble technetium-99m complexes showed significant brain uptake, 1.54 and 1.07% dose/organ at 2 min for [99mTc]TcVO(U-BAT) and TcVO(OU-BAT), respectively. The novel Tc chemistry of this new ligand system may provide a useful foundation for designing Tc complexes with a built-in redox mechanism.

Animals↗
PubMed2006

[Piperazines as model substrate for oxidations].

Piperazines as model substrate for oxidations Piperazine derivatives when being oxidized by mercury-EDTA behave unusually. Due to the reactive cyclic enediamine intermediates as aza-analogous reductones and to the carbonyl compounds resulting from dehydrogenation in the side chain, there exists a high tendency of polymerization. 1-Benzylpiperazines 5a-d generate the piperazine-2,3-diones 8a-d in medium yields. From 1-benzhydrylpiperazine 11 results a mixture of piperazine-2,3-dione 12 and piperazine-3-on 13. The 1,4-bis-substituted piperazines react more differently because of the symmetry and the preferred direction of the dehydrogenation into the cycle. Thus, from 15 and 19 the diones 16 and 20, respectively, were available in very good yields. A mechanism for the reactions is proposed.

Benzyl Compounds↗
PubMed2005

Synthesis, spectral study and cytotoxicity of platinum(II) complexes with 2,9-disubstituted-6-benzylaminopurines.

A series of platinum(II) complexes with 2,9-disubstituted-6-benzylaminopurines has been prepared. The complexes have the following composition: cis-[Pt(Boh)(2)Cl(2)] (1), cis-[Pt(Oc)(2)Cl(2)] (2), cis-[Pt(Ros)(2)Cl(2)] (3), cis-[Pt(i-PrOc)(2)Cl(2)] (4), cis-[Pt(BohH(+))(2)Cl(2)]Cl(2) (5), cis-[Pt(OcH(+))(2)Cl(2)]Cl(2) (6), cis-[Pt(RosH(+))(2)Cl(2)]Cl(2) (7) and cis-[Pt(i-PrOcH(+))(2)Cl(2)]Cl(2) (8), where Boh=2-(3-hydroxypropylamino)-6-benzylamino-9-isopropylpurine, Oc=2-(2-hydroxyethylamino)-6-benzylamino-9-methylpurine, Ros=2-(R)-(1-ethyl-2-hydroxyethylamino)-6-benzylamino-9-isopropylpurine and i-PrOc=2-(2-hydroxyethylamino)-6-benzylamino-9-isopropylpurine. The complexes have been characterized by elemental analyses, conductivity measurements and their infrared, ES+mass (electrospray mass spectra in the positive ion mode) and NMR ((1)H, (13)C, (15)N and (195)Pt) spectra. The results obtained from the physical studies, particularly from multinuclear NMR spectroscopy, show that in all the investigated complexes (1-8), two molecules of purine derivative are coordinated to platinum via the N(7) atom of the imidazole ring in a cis-configuration. The prepared compounds have been screened for their in vitro cytotoxicity against G-361 (human malignant melanoma), HOS (human osteogenic sarcoma), K-562 (human chronic myelogenous leukemia) and MCF-7 (human breast adenocarcinoma) cell lines. All complexes are significantly more active than the initial 2,9-disubstituted-6-benzylaminopurine derivatives. In the case of some tumour cell lines, IC(50) values for the complexes (1, 3, 4, 5, 8) are significantly lower than those obtained for cisplatin and oxaliplatin. The best cytotoxicity was achieved for the complex (3) for which IC(50) values range from 1 to 2 microM.

Antineoplastic Agents↗
PubMed2003

Hepatoprotective effect of myristicin from nutmeg (Myristica fragrans) on lipopolysaccharide/d-galactosamine-induced liver injury.

To evaluate the hepatoprotective activity of spices, 21 different spices were fed to rats with liver damage caused by lipopolysaccharide (LPS) plus d-galactosamine (D-GalN). As assessed by plasma aminotranferase activities, nutmeg showed the most potent hepatoprotective activity. Bioassay-guided isolation of the active compound from nutmeg was carried out in mice by a single oral administration of the respective fractions. Myristicin, one of the major essential oils of nutmeg, was found to possess extraordinarily potent hepatoprotective activity. Myristicin markedly suppressed LPS/D-GalN-induced enhancement of serum TNF-alpha concentrations and hepatic DNA fragmentation in mice. These findings suggest that the hepatoprotective activity of myristicin might be, at least in part, due to the inhibition of TNF-alpha release from macrophages. However, further studies are needed to elucidate the hepatoprotective mechanism(s) of myristicin.

Alanine Transaminase↗
PubMed1998

The contractile effect of fedotozine on guinea pig isolated intestinal cells is not mediated by kappa opioid receptors.

The compound fedotozine, recently described as a peripheral kappa opioid receptor agonist, was tested on smooth muscle cells isolated from the longitudinal muscle layer of the guinea pig ileum, in comparison with the selective kappa receptor agonist, compound U-50488. Fedotozine (1 nmol/l-1 micromol/l) caused a concentration-dependent contraction of intestinal cells, with a maximum decrease in cell length not significantly different from that caused by acetylcholine. The kappa agonist U-50488 (0.1 pmol/l-100 nmol/l) was without effect. The contractile effect of fedotozine was not significantly modified by naloxone (0.1-1 micromol/l). These results indicate that fedotozine can have direct excitatory effects on intestinal smooth muscle cells from the guinea pig ileum not mediated by activation of kappa opioid receptors.

3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)-cycloh↗
PubMed1985

Biocide patch tests.

Routine patch testing with a series of 6 industrial biocides containing methylene-bis-thiocyanate (Cytox 3522), benzisothiazolin-3-one (BIT), chlorocresol (Preventol CMK), 2-n-octyl-4-isothiazolin-3-one (Kathon 893), polyhydroxymethylene monobenzylether (Preventol D2) or 1,3,5-tris (hydroxy-ethyl) hexahydrotriazine (Grotan BK) was carried out in 6 Danish out-patient clinics to evaluate guinea pig allergy test results with the same compounds. A total of 1652 consecutive patients with dermatitis were tested. The usefulness of this patch test battery was limited. There were a few positive reactions to Cytox 3522, BIT and the 2 formaldehyde releasers, Preventol D2 and Grotan BK. These reactions could not, however, be explained. The MOAHL-index (% of Male patients, Occupational cases, Atopic patients, Hand eczemas, and Leg ulcers/stasis dermatitis) for patients from the 6 clinics showed equal frequencies of male patients and atopics, but significant differences in the frequencies of occupational cases, hand eczemas, and leg ulcers/stasis dermatitis, indicating possible variations in referral patterns, use of patch tests, and/or environmental factors.

Animals↗
PubMed2002

Amyloplast formation in cultured tobacco BY-2 cells requires a high cytokinin content.

When cytokinin-autonomous tobacco BY-2 cell cultures are transferred into 2,4-dichlorophenoxyacetic acid (2,4-D)-deprived medium, amyloplast development is initiated. Using this in vitro amyloplast-inducing system, the role of cytokinins in amyloplast formation was investigated. We show that addition of lovastatin, an inhibitor of mevalonate synthesis, to amyloplast-inducing medium reduced starch accumulation. Microscopic observation also revealed that lovastatin treatment decreased starch deposition; however, the overall morphologies of cells and plastids were less affected than control cell cultures. In addition, lovastatin lowered the transcription level of the ADP-glucose pyrophosphorylase small subunit (AgpS) gene. Application of mevalonate or zeatin dramatically restored the decrease in starch deposition, and restored AgpS mRNA accumulation. Moreover, addition of other molecules with cytokinin activity, such as adenine- and phenylurea-type compounds, restored starch accumulation and AgpS transcript levels, whereas other isopentenyl pyrophosphate-derived phytohormones did not. Liquid chromatography-mass spectrometry/mass spectrometry quantification of endogenous cytokinins revealed that endogenous cytokinins increased when BY-2 cells were transferred into 2,4-D-deprived medium from conventional medium containing 2,4-D. In addition, lovastatin treatment decreased endogenous cytokinins to some extent when cultured under 2,4-D-deprived conditions. Our results suggest that both 2,4-D deprivation and an increase in endogenous cytokinins have important roles in accelerating the changes in plastid morphology, starch accumulation, and AgpS gene expression.

2,4-Dichlorophenoxyacetic Acid↗
PubMed1978

Benzyloxycarbonylarginine nitrophenyl ester salts: 1-hydroxybenzotriazole catalyzed acylations of amines.

Benzyloxycarbonylarginine p-nitrophenyl ester has been prepared by the p-nitrophenyltrifluoroacetate method. The p-nitrophenyl ester derivative was isolated as its crystalline picrate and nitrate salts. The ester salts couple with amino compounds in the presence of 1-hydroxybenzotriazole, but decompose without acylation of amines in the absence of the 1-hydroxybenzotriazole catalyst. Benzyloxycarbonylarginine p-nitrophenyl ester and other activated esters of N-a-sustituted arginine salts may be useful reagents for introduction of trypsin-labile protecting groups into peptide fragments for purpose of polypeptide semi-synthesis. At the same time, side reactions of such carboxyl-activated arginine derivatives may serve as models for side reactions in the couplings of peptide fragments with arginine residues in the carboxyl-terminal position. Peptide fragment couplings of this type may frequently be encountered in semisynthesis of polypeptides from tryptic fragments.

Acylation↗
PubMed1994

Structure-activity relationships in a series of 5-[(2,5-dihydroxybenzyl)amino]salicylate inhibitors of EGF-receptor-associated tyrosine kinase: importance of additional hydrophobic aromatic interactions.

Potent inhibitors of EGF-dependent protein tyrosine kinase (PTK) activity were synthesized in a series of 5-[(2,5-dihydroxybenzyl)amino]salicylates. Several of these compounds inhibited EGF-dependent DNA synthesis in ER 22 cells with IC50 < 1 microM. In this series of PTK inhibitors, the role of the salicylate moiety as a potential divalent ion chelator was tested and found to be nonessential in all cases. The length and ramification of the substituting carboxyl group were investigated to improve cellular bioavailability, and this analysis provided compounds with increased inhibitory effect on EGF-induced DNA synthesis. Salicylates esterified with long hydrophobic chains were shown to be noncompetitive inhibitors of ATP, in contrast to the free acid and methyl salicylate. Moreover, all the tested inhibitors were shown to be noncompetitive inhibitors of the peptide substrate. Structure-activity relationships allowed us to suspect a hydrophobic pocket in the tyrosine kinase domain, preferentially interacting with aromatic rings. Finally, the selectivity of the best inhibitors was tested against other kinases, and they were found to be selective for tyrosine kinase. They were also shown to be good inhibitors of EGF-receptor autophosphorylation.

Animals↗
PubMed1989

[The biotransformation of leiocarposide and salicin phenol glycosides--examples for special consideration of the absorption and metabolism of glycosidic compounds].

After parenteral administration of leiocarposide (1, 3-beta-D-glucopyranosyloxy-2-methoxy-6-hydroxybenzoic acid-2'-beta-D-glucopyranosyloxybenzylester) and salicin to the rat the glycosides were mostly excreted unchanged in urine. In contrast to the oral administration (see [1]) only small amounts of metabolites [1: 0.2% of the dose as leiocarpic acid and 0.1% salicylic acid; 2: 0.05% 5] were observed. By in vitro experiments could be shown, that the hydrolysis of ester and glycosidic bonds from 1 to 3 and saligenin and from 2 to 4 took place microbially mostly in the cecum and colon of the rats. The reactions are also visible in the homogenate of kidney. Präparations of liver, lung and serum showed no activity. 4 in the homogenates of liver, kidney and lung, in the gut-wall and the serum was oxidized to 5. The further product of oxidation of 5, gentisic acid, arise only in liver homogenate.

Animals↗
PubMed1987

Biological conversion of benzaldehyde to benzylmercapturic acid in the Sprague-Dawley rat.

The metabolism of benzaldehyde was investigated in Sprague-Dawley rats. After repeated oral administration of this compound (0.4-1.0 g/kg) for 13 consecutive days, urine was collected and analyzed for the presence of metabolites. The acidification of the pooled urine samples (pH:2.0) with 6 N H2SO4 was followed by ethyl acetate extraction, evaporation of the extract and methylation with diazomethane. Identification of the metabolite by comparison with a synthetic sample of benzylmercapturic acid (BENZM) was conducted by gas chromatography. Mass spectrometry examination of this metabolite revealed the following peaks characteristic of benzylmercapturic acid: m/z (%), 91(100), 176(27), 208(23), 43(20), 88(13), 117(10), 134(9), M+ 267(2). Monitoring of urines from both female and male rats showed a dose-related increase of benzylmercapturic acid which was found to be a reliable indicator of exposure to benzaldehyde.

Acetylcysteine↗
PubMed1997

[Bactericidal activity determination of Biseptine, combination of chlorhexidine, benzalkonium chloride and benzylic alcohol, on 124 hospital bacterial strains].

Biseptine is an antiseptic composed of chlorhexidine digluconate (CHX), benzalkonium chloride (BC) and benzylic alcohol. Minimal Bactericidal Concentrations (MBCs) of Biseptine were determined on 124 clinical strains: 76 Enterobacteriaceae, 16 other Gram negative bacilli, (Pseudomonas spp, Aeromonas spp, Haemophilus spp) and 32 Gram positive bacteria (Staphylococcus spp, Streptococcus spp, Listeria spp, Bacillus cereus), using microdilution method, in comparison with Hibitane Champ. Modal MBC of Biseptine was 25 mg/l of CHX/2.5 mg/l BC (1/100 dilution). Proteus (MBC: 133 mg/l CHX/ 13 mg/l CB) and B. cepacia (MBC: 100 mg/l CHX/ 10 mg/l CB) were the most resistant strains, as expected with cationic antiseptics. 4/5 Bacillus cereus, strains were weakly susceptible to Biseptine and Hibitane Champ. In Biseptine, the association of CHX and CB showed a synergic activity, MBCs are usually 2 fold lower that Hibitane Champ MBCs.

Anti-Infective Agents, Local↗
PubMed1998

Biologically active oligodeoxyribonucleotides. Part 11: The least phosphate-modification of quadruplex-forming hexadeoxyribonucleotide TGGGAG, bearing 3-and 5-end-modification, with anti-HIV-1 activity.

We have found that a hexadeoxyribonucleotide (5'TGGGAG3', R-95288), Koizumi, M. et al. Bioorganic & Medicinal Chemistry, 1997, 5, 2235, bearing a 3,4-dibenzyloxybenzyl (3,4-DBB) group at the 5'-end and a 2-hydroxyethylphosphate at the 3'-end, has high anti-HIV-1 activity and the least cytotoxicity in vitro and in vivo. In order to synthesize more potent hexadeoxyribonucleotides, we substituted phosphodiester (P-O) bonds in the 6-mer with the least phosphorothioate (P-S), phosphoramidate (P-N), or methylphosphonate (P-Me) bonds. When more than two P-N or P-Me bonds were introduced into a 6-mer, the phosphate-modified 6-mers had weak or no anti-HIV- activity, in spite of quadruplex structure formation. However, when P-S bonds were substituted for P-O bonds, anti-HIV-1 activity of their 6-mers did not dramatically decrease, compared with compounds substituted with P-N or P-Me bonds. The results suggest that the formation of a quadruplex structure is not always sufficient for anti-HIV-1 activity of the 6-mer, and that net negative charges derived from P-O or P-S bonds in the quadruplex are important for anti-HIV-1 activity. Moreover, among various phosphate-modified ODNs, we found that the anti-HIV-1 activity of ODN PS7 with only one P-S bond was the same as that of R-95288, both having a high stability in human plasma.

Anti-HIV Agents↗
PubMed2005

Synthesis and evaluation of N-(5-fluoro-2-phenoxyphenyl)-N-(2-[(18)F]fluoromethoxy-d(2)-5-methoxybenzyl)acetamide: a deuterium-substituted radioligand for peripheral benzodiazepine receptor.

N-(5-Fluoro-2-phenoxyphenyl)-N-(2-[(18)F]fluoromethoxy-d(2)-5-methoxybenzyl)acetamide ([(18)F]2) is a potent ligand (IC(50): 1.71 nM) for peripheral benzodiazepine receptor (PBR). However, in vivo evaluation on rodents and primates showed that this ligand was unstable and rapidly metabolized to [(18)F]F(-) by defluorination of the [(18)F]fluoromethyl moiety. In this study, we designed a deuterium-substituted analogue, N-(5-fluoro-2-phenoxyphenyl)-N-(2-[(18)F]fluoromethoxy-d(2)-5-methoxybenzyl)acetamide ([(18)F]5) as a radioligand for PBR to reduce the in vivo metabolic rate of the non-deuterated [(18)F]2. The design principle was based on the hypothesis that the deuterium substitution may reduce the rate of defluorination initiated by cleavage of the C-H bond without altering the binding affinity for PBR. The non-radioactive 5 was prepared by reacting diiodomethane-d(2) (CD(2)I(2), 6) with a phenol precursor 7, followed by treatment with tetrabutylammonium fluoride. The ligand [(18)F]5 was synthesized by the alkylation of 7 with [(18)F]fluoromethyl iodide-d(2) ([(18)F]FCD(2)I, [(18)F]9). Compound 5 displayed a similar in vitro affinity to PBR (IC(50): 1.90 nM) with 2. In vivo evaluation demonstrated that [(18)F]5 was metabolized by defluorination to [(18)F]F(-) as a main radioactive component, but its metabolic rate was slower than that of [(18)F]2 in the brain of mice. The deuterium substitution decreased the radioactivity level of [(18)F]5 in the bone of mouse, augmented by the percentage of specific binding to PBR in the rat brain determined by ex vivo autoradiography. However, the PET image of [(18)F]5 for monkey brain showed high radioactivity in the brain and skull, suggesting a possible species difference between rodents and primates.

Acetamides↗
PubMed1996

[Kinetics of in vitro bactericidal activity of the antiseptic biseptine combining 3 active principles].

Biseptine, is an association of chlorhexidine digluconate, benzalkonium chloride and benzylic alcohol. Little is known, in literature, on this antiseptic, used for cutaneous antisepsis. We studied killing kinetic of Biseptine, at different concentrations, on 4 AFNOR bacterial strains. Killing curves were studied at antiseptic concentration of 90 to 0.1% in 10 ml of distilled water. Bacterial counts were determined after neutralization in liquid medium. Synergy of chlorhexidine and benzalkonium chloride in Biseptine, allowed to obtain similar bactericidal activity than Hibitane champ with chlorhexidine concentrations 2 fold less. At 90, 50, 25, 10 and 5% concentrations, bactericidal activity (5 log10 reduction of the initial bacterial count) was effective in one minute. After 5 to 15 minutes, activity persisted at 1 and 0.5% concentrations. The 0.1% solution was inefficacious. This report disclosed an important security margin in antiseptic activity.

Anti-Infective Agents, Local↗