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PubMed2001

The amber codon in the gene encoding the monomethylamine methyltransferase isolated from Methanosarcina barkeri is translated as a sense codon.

Each of the genes encoding the methyltransferases initiating methanogenesis from trimethylamine, dimethylamine, or monomethylamine by various Methanosarcina species possesses one naturally occurring in-frame amber codon that does not appear to act as a translation stop during synthesis of the biochemically characterized methyltransferase. To investigate the means by which suppression of the amber codon within these genes occurs, MtmB, a methyltransferase initiating metabolism of monomethylamine, was examined. The C-terminal sequence of MtmB indicated that synthesis of this mtmB1 gene product did not cease at the internal amber codon, but at the following ochre codon. Antibody raised against MtmB revealed that Escherichia coli transformed with mtmB1 produced the amber termination product. The same antibody detected primarily a 50-kDa protein in Methanosarcina barkeri, which is the mass predicted for the amber readthrough product of the mtmB1 gene. Sequencing of peptide fragments from MtmB by Edman degradation and mass spectrometry revealed no change in the reading frame during mtmB1 expression. The amber codon position corresponded to a lysyl residue using either sequencing technique. The amber codon is thus read through during translation at apparently high efficiency and corresponds to lysine in tryptic fragments of MtmB even though canonical lysine codon usage is encountered in other Methanosarcina genes.

Amino Acid Sequence↗
PubMed2003

Methanethiosulfonate ethylammonium block of amine currents through the ryanodine receptor reveals single pore architecture.

The homotetrameric structure of the ryanodine-sensitive intracellular calcium (Ca2+) release channel (ryanodine receptor (RyR)) suggests that the four RyR subunits either combine to form a single pore or that each RyR subunit is an independently conducting pathway. Previously we showed that methanethiosulfonate ethylammonium (MTSEA+) covalently modifies the RyR to reduce current amplitudes in a time-dependent and stepwise manner. To ascertain the number of functionally conducting pores in the RyR, two approaches were combined: modification of the receptor by MTSEA+ and the use of different sized current carriers. Previous reports (Tinker, A., and Williams, A. J. (1993) J. Gen. Physiol. 102, 1107-1129) have shown that the organic cations methylamine, dimethylamine, ethylamine, and trimethylamine are permeant through the RyR but with reduced current amplitude depending upon the diameter of the respective amine. Experiments using the thiol reagent MTSEA+ to modify the channel protein showed that the current amplitudes decrease in steps leading to complete block of the channel when cesium (Cs+) is the current carrier. MTSEA+ modification decreased the number of channel substates as the diameter of the current carrier increased. Comparison of the degree of inhibition of MTSEA+-modified currents allows for differentiation between the two models for channel architecture. These results demonstrate that the conduction pathway for the RyR is comprised of a single central pore.

Amines↗
PubMed2005

Organic cation permeation through the channel formed by polycystin-2.

Polycystin-2 (PC2), a member of the transient receptor potential family of ion channels (TRPP2), forms a calcium-permeable cation channel. Mutations in PC2 lead to polycystic kidney disease. From the primary sequence and by analogy with other channels in this family, PC2 is modeled to have six transmembrane domains. However, most of the structural features of PC2, such as how large the channel is and how many subunits make up the pore of the channel, are unknown. In this study, we estimated the pore size of PC2 from the permeation properties of the channel. Organic cations of increasing size were used as current carriers through the PC2 channel after PC2 was incorporated into lipid bilayers. We found that dimethylamine, triethylamine, tetraethylammonium, tetrabutylammonium, tetrapropylammonium, and tetrapentylammonium were permeable through the PC2 channel. The slope conductance of the PC2 channel decreased as the ionic diameter of the organic cation increased. For each organic cation tested, the currents were inhibited by gadolinium and anti-PC2 antibody. Using the dimensions of the largest permeant cation, the minimum pore diameter of the PC2 channel was estimated to be at least 11 A. The large pore size suggests that the primary state of this channel found in vivo is closed to avoid rundown of cation gradients across the plasma membrane and excessive calcium leak from endoplasmic reticulum stores.

Animals↗
PubMed2005

The residue mass of L-pyrrolysine in three distinct methylamine methyltransferases.

Single in-frame amber (UAG) codons are found in the genes encoding MtmB, MtbB, or MttB, the methyltransferases initiating methane formation from monomethylamine, dimethylamine, or trimethylamine, respectively, in certain Archaea. The crystal structure of MtmB demonstrated that the amber codon codes for pyrrolysine, the 22nd genetically encoded amino acid found in nature. Previous attempts to visualize the amber-encoded residue by mass spectrometry identified only lysine, leaving information on the existence and structure of pyrrolysine resting entirely on crystallography of a single protein. Here we report successful mass spectral characterization of naturally occurring pyrrolysine and the first demonstration of the amber-encoded residue in proteins other than MtmB. The sequencing of chymotryptic fragments from acetonitrile-denatured proteins by tandem mass spectrometry revealed the mass of the amber-encoded residue in MtmB, MtbB, and MttB as 237.2 +/- 0.2 Da. Fourier transform ion cyclotron resonance mass spectrometry produced an accurate measurement for the pyrrolysyl-residue as 237.1456 Da, within error limits of the predicted mass based on the empirical formula C(12)H(19)N(3)O(2). These measurements support the structure of pyrrolysine in MtmB as 4-methylpyrroline-5-carboxylate in amide linkage with the (epsilon)N of lysine but not the alternative structure in which the 4-substituent of the pyrroline ring is an amine group. The presence of pyrrolysine with statistically identical mass in all three methyltransferases is in keeping with the proposed direct incorporation of pyrrolysine into protein during translation of the UAG codon and suggests that MtbB and MttB may exploit the unusual electrophilicity of pyrrolysine during catalysis.

Amides↗
PubMed2002

Pharmacokinetics and metabolism of the anti-oestrogen droloxifene in female human subjects.

1. Single oral doses of a solution formulation of (14)C-droloxifene citrate (141 mg) appeared to be rapidly and well absorbed in four post-menopausal female subjects. Peak plasma concentrations (C(max)) of total (14)C (1260 ng eq. ml(-1)), droloxifene (196 ng ml(-1)) and the major metabolite droloxifene glucuronide (851 ng eq. ml(-1)) occurred at 0.9-1.1 h (T(max)) and declined bi-exponentially with terminal half-lives of 45.0, 31.6 and 32.0 h respectively. The mean AUCs of droloxifene and the major metabolite were 21 and 37% respectively that of total (14)C. 2. Total (14)C was excreted slowly, mainly in the faeces. Mean totals of 6.6 and 90.3% of the dose were excreted in the urine and faeces respectively during 11 days. The data were consistent with biliary excretion and enterohepatic circulation of the major metabolite, droloxifene glucuronide. 3. GC-MS showed that the major (14)C-components in 0-24-h urine were droloxifene (mean 0.4% dose) and its glucuronide (2.3% dose), and in faeces were droloxifene (60.2% dose) and N- desmethyldroloxifene (4.2% dose). Other components in faeces corresponded chromatographically to reference standards, droloxifene N-oxide (1.9% dose), side-chain hydroxylated droloxifene (dimethylamine moiety of droloxifene side-chain replaced by hydroxyl, 1.3% dose) and droloxifene glucuronide (10.7% dose). The latter was resistant to enzymic hydrolysis by the beta-glucuronidase used. 4. Intersubject variability in the pharmacokinetics of droloxifene in this study was relatively low (CV < 20% for AUC and half-life).

Area Under Curve↗
PubMed1997

Localization, depuration, bioaccumulation and impairment of ion regulation associated with cationic polymer exposure in rainbow trout (Oncorhynchus mykiss).

1. Static exposure of rainbow trout, Oncorhynchus mykiss, to three commercial 14C-labelled cationic polymers (EDP, epichlorhydrin-dimethylamine; CYT, polyacrylamide ester; and STK, polyacrylamide amide) resulted in 14C being concentrated only in gill tissue. 2. Depuration studies examining the effect of humic acid (HA) on cationic polymer bound in gill tissue indicate that the binding is reversible with exposure to polymer-free water and polymer-free water with HA for each of the three polymers. 3. Analysis of blood pH, Na+, K+, total NH3 and Cl- after static water exposures to EDP (m.w. 50,000) at 7.5 mg EDP/l revealed a treatment related decrease in blood pH, from 7.1 to 6.6, accompanied by an increase in blood NH3 and evidence of severe impairment of ion regulation. 4. Repeated exposure to the cationic polymers did not result in increases in the 14C concentration in gill tissue suggesting that bioaccumulation of the polymers does not occur. 5. These data suggest that the gill is the site of toxicity for these cationic polymers and that their toxic effects involve gill function and ion regulation rather than systemic actions on internal organs.

Acrylic Resins↗
PubMed1983

HPLC--residue analysis of the herbicide pyridate in cereals.

For many reasons residue analysis of plant protecting chemicals is becoming of increasing importance. The demand of modern trace analysis techniques is to detect significantly and sensitively values down to levels in the ppb range or even less. Aggravating circumstances are the complex multicomponent sample matrices out of whom the residue analysis has to be performed; theoretically thousands of compounds could be present and interferences with substances of interest are quite likely. One way to get around these difficulties is to employ multidimensional HPLC (MD-HPLC). A method using this invaluable analytical tool tracing Pyridate and its main metabolites in various plant extracts is presented. Based on a brief discussion about requirements of modern trace analysis HPLC in connection with column switching we designed an automatizable setup combining a weak anionexchanger (dimethylamine phase) with a reversed phase system handling relatively large aqueous sample volumes. Depending on specifically described sample pretreatment schemes detection limits down to 30 ppb are routinely obtained. At this level acceptable on-line UV-spectra can be obtained via inserting a spectrophotometric detector in a loop of a 6-port valve. The usefulness of the method described has been demonstrated by analysing several hundred samples.

Chromatography, High Pressure Liquid↗
PubMed1999

8-Amino-2'-deoxyguanosine incorporation into oligomeric DNA.

During the incorporation of 8-amino-dG into oligomeric DNA, the deprotection conditions previously recommended (28% ammonia at room temperature) do not effect complete removal of the dimethylaminomethylene protecting groups. At elevated temperatures oxidative degradation of the oligomer and exchange of ammonia with dimethylamine in the protecting group at C8 occurred. The resolution of these problems and a method to obtain a series of homogeneous oligomers in reasonable yield containing 8-amino-dG located site-specifically are described.

Base Sequence↗
PubMed1990

Dissociation between maternal and fetal toxicity of methyl isocyanate in mice and rats.

The contribution of maternal hormonal changes and pulmonary damage on the fetal toxicity of methyl isocyanate (MIC) was studied in mice and rats. Exposure to MIC decreased maternal plasma progesterone levels in mice that lost but not in mice that retained pregnancy. Fetal toxicity of MIC was not related to changes in maternal plasma corticosterone levels. Neither chronic administration of progesterone nor the suppression of pulmonary edema with dexamethasone decreased fetal toxicity of MIC. Embryos exposed in utero or in vitro to MIC vapor exhibited a concentration-dependent decrease in growth in culture. An acute dose (3 mmol/kg) of the MIC metabolites (methylamine, dimethylamine, trimethylamine, dimethyl urea) did not exert fetal toxicity. These data suggest that the fetal toxicity of MIC is partly independent of maternal toxicity and may result from its transfer across the placenta and interaction with fetal tissues.

Administration, Inhalation↗
PubMed1983

Collection and ion chromatographic determination of ammonia and methylamines in air.

A method is described for the collection of ammonia (NH3), monomethylamine (MMA), dimethylamine (DMA), and trimethylamine (TMA) from air and their subsequent determination by ion chromatography. Samples are collected with 800-mg silica gel sampling tubes at a flow rate of 1 L/min for 10 minutes or at 100 mL/min for up to 7.5 hours. Samples collected with sulfuric acid-treated tubes can be stored at room temperature for at least 21 days with no loss in recovery. Untreated samples can be stored in a refrigerator up to 32 days. The method has been validated from 2 to 50 ppm v/v when a 10 L air sample is taken. No loss in recovery was observed when sampling up to 23 L of air at 100% relative humidity. The recovery and total precision (95% confidence level) for NH3, MMA, DMA, and TMA were 91 +/- 12.5%, 93 +/- 10.3%, 92 +/- 9.6% and 84 +/- 17.6%, respectively.

Air Pollutants↗
PubMed1985

Validation of techniques for the destruction of dimethyl sulfate.

It has been reported that dimethyl sulfate (DMS) can be degraded with sodium hydroxide solution (1 mol/L), sodium carbonate solution (1 mol/L), or ammonium hydroxide solution (1.5 mol/L). This has now been confirmed. Complete destruction of undiluted DMS or DMS in solvents miscible with water (methanol, ethanol, DMSO, DMF, acetone) or solvents partially miscible or immiscible with water (toluene, p-xylene, benzene, 1-pentanol, ethyl acetate, chloroform, carbon tetrachloride, acetonitrile) could be obtained using any of the above methods. Reaction times were 15 min after homogeneity was obtained for undiluted DMS, 15 min for solutions in methanol, ethanol, DMSO, and DMF, one hour for solutions in acetone, three hours for acetonitrile, and one day for the other solvents listed above. The final reaction mixtures were tested for mutagenicity, and when the solutions were not cytotoxic, no mutagenic response was obtained. DMS in solution was determined by a colorimetric method. The products of the reactions were found to be methanol when NaOH and Na2CO3 were used and methylamine, dimethylamine, trimethylamine, and methanol when ammonium hydroxide was used. The stability of DMS in various solvents was also determined.

Animals↗
PubMed1985

Formaldehyde: a comparative evaluation of four monitoring methods.

The performances of four formaldehyde monitoring devices were compared in a series of laboratory and field experiments. The devices evaluated included the DuPont C-60 formaldehyde badge, the SKC impregnated charcoal tube, an impinger/polarographic method and the MDA Lion formaldemeter. The major evaluation parameters included: concentration range, effects of humidity, sample storage, air velocity, accuracy, precision, interferences from methanol, styrene, 1,3-butadiene, sulfur dioxide and dimethylamine. Based on favorable performances in the laboratory and field, each device was useful for monitoring formaldehyde in the industrial work environment; however, these devices were not evaluated for residential exposure assessment. The impinger/polarographic method had a sensitivity of 0.06 ppm, based on a 20-liter air sample volume, and accurately determined the short-term excursion limit (STEL). It was useful for area monitoring but was not very practical for time-weighted average (TWA) personal monitoring measurements. The DuPont badge had a sensitivity of 2.8 ppm-hr and accurately and simply determined TWA exposures. It was not sensitive enough to measure STEL exposures, however, and positive interferences resulted if 1,3-butadiene was present. The SKC impregnated charcoal tube measured both TWA and STEL concentrations and had a sensitivity of 0.06 ppm based on a 25-liter air sample volume. Lightweight and simple to use, the MDA Lion formaldemeter had a sensitivity of 0.2 ppm. It had the advantage of giving an instantaneous reading in the field; however, it must be used with caution because it responded to many interferences. The method of choice depended on the type of sampling required, field conditions encountered during sampling and an understanding of the limitations of each monitoring device.

Air Pollutants, Occupational↗
PubMed1971

The permeability of the sodium channel to organic cations in myelinated nerve.

The relative permeability of sodium channels to 21 organic cations was studied in myelinated nerve fibers. Ionic currents under voltage-clamp conditions were measured in sodium-free solutions containing the test cation. The measured reversal potential and the Goldman equation were used to calculate relative permeabilities. The permeability sequence was: sodium approximately hydroxylamine > hydrazine > ammonium approximately formamidine approximately guanidine approximately hydroxyguanidine > aminoguanididine >> methylamine. The cations of the following compounds were not measurably permeant: N-methylhydroxylamine, methylhydrazine, methylamine, methylguanidine, acetamidine, dimethylamine, tetramethylammonium, tetraethylammonium, ethanolamine, choline, tris(hydroxymethyl)amino methane, imidazole, biguanide, and triaminoguanidine. Thus methyl and methylene groups render cations impermeant. The results can be explained on geometrical grounds by assuming that the sodium channel is an oxygen-lined pore about 3 A by 5 A in cross-section. One pair of oxygens is assumed to be an ionized carboxylic acid. Methyl and amino groups are wider than the 3 A width of the channel. Nevertheless, cations containing amino groups can slide through the channel by making hydrogen bonds to the oxygens. However, methyl groups, being unable to form hydrogen bonds, are too wide to pass through.

Amidines↗
PubMed1991

Inhibition of nitrosamine formation by ascorbic acid.

Nitrosation occurs under a wide variety of conditions by reaction of most types of amines with any of a large number of nitrosating species. Nitrite can be formed in vivo via bacterial reduction of nitrate and by activated macrophages and endothelial cells. The mechanism of nitrite formation by mammalian cells is via enzymatic oxidation of arginine to NO followed by oxidation to N2O3 and N2O4. Nitrosatable amines are found in many foods and some, eg, dimethylamine, are synthesized in the body. Precursors of N-nitroso compounds are thus almost constantly present together under favorable reaction conditions in vivo and there is, consequently, considerable interest concerning possible human health risks arising from endogenous formation of this class of compounds. Among many nitrosation inhibitors, most attention has focused on ascorbic acid, which reacts with many nitrosating agents and which is virtually nontoxic. This presentation discusses the chemistry of ascorbic acid inhibition of nitrosation reactions.

Amines↗
PubMed1993

Use of the [14C]aminopyrine breath test to assess the hepatic response of dietary obese rats to a very-low-energy diet.

The intake of a very-low-energy diet (VLED) complete in all essential nutrients decreases liver mass and total liver protein in dietary obese rats. To determine how these findings may affect hepatic drug metabolizing activity, the aminopyrine breath test was performed in nine male dietary obese Sprague-Dawley rats weighing 440-460 g. Animals were maintained on a VLED, and at 0, 14, and 21 d were injected with 9.25 k Bq (0.25 microCi) [dimethylamine-14C]aminopyrine and placed in airtight restraining cages; exhaled 14CO2 was collected for 120 min. VLED animals had an increased half-life of exhaled 14CO2 (P < 0.01) and a decreased rate constant of aminopyrine elimination (P < 0.01) consistent with decreased N-demethylation of aminopyrine. Decreased liver glutathione suggests reduced ability to detoxify drugs through this conjugation pathway. These studies suggest that animals on VLEDs have reduced capacity for demethylation of aminopyrine as measured by oxidative elimination of 14CO2, and may exhibit decreased metabolism of other drugs.

Aminopyrine↗
PubMed1989

In vivo inhibition of N-nitrosodimethylamine metabolism by 4-methylpyrazole: a model for endogenous nitrosation.

The endogenous formation of N-nitrosodimethylamine (NDMA) was investigated in the ferret by inhibiting metabolism and monitoring urinary NDMA levels. The addition of 1.0 mg/ml of 4-methylpyrazole (4-MP) to the drinking water was sufficient to allow a 13% urinary recovery of a 4.0 nmol oral dose of NDMA to be made in 24 h. Without 4-MP, no NDMA could be detected in urine. There was no detectable urinary NDMA when dimethylamine (DMA) alone was given but when as little as 5 mumol of nitrite and 0.75 mmol of DMA were given, the urine contained approximately 0.3 nmol NDMA/day. Nitrite doses of 0-100 mumol along with 0.75 mmol of DMA resulted in a dose-dependent excretion of less than 0.1-2.5 nmol NDMA/day. When 10 mumol of aminopyrine was substituted for DMA and 40 mumol of nitrite given, the excretion of NDMA was 10 nmol day. Administration of ascorbic acid inhibited NDMA excretion and thiocyanate increased NDMA formation. Consumption of foods containing trace amounts of NDMA resulted in the excretion of NDMA but in most cases at levels that were lower than those ingested in the food. These data suggest that mumol amounts of nitrite can result in the endogenous formation of nmol amounts of NDMA in the acidic environment of the stomach. It also suggests that short-term ingestion of 4-MP might be an approach to studying the possible endogenous formation of NDMA in humans.

Animals↗
PubMed1989

Mutational specificities of environmental carcinogens in the lacI gene of Escherichia coli. I. The direct-acting analogue N-nitroso-N-methyl-N-alpha-acetoxymethylamine.

The mutational specificity of N-nitroso-N-methyl-N-alpha-acetoxymethylamine in Escherichia coli has been determined through the DNA sequence characterization of 190 forward mutations in the lacI gene. Consistent with the methylating ability of this compound and the predicted mutagenic potential of O6-methylguanine damage, the predominant mutation was the G:C----A:T transition. An analysis of the neighbouring template revealed a similar 5' flanking sequence influence on G:C----A:T site mutability reported for other direct-acting SN1 alkylating agents. However, a dose-dependency was observed. The preference for transition at guanine residues flanked (5') by a purine over those preceded by a pyrimidine decreased from a ratio of 19:1 (upon 1 mM treatment) to 6:1 (upon 10 mM treatment) and 4:1 (upon 30 mM treatment). Two double G:C----A:T transition mutants were characterized. In addition, this nitrosamine appears to be relatively more efficient at producing other kinds of mutations. In total 19 non-G:C----A:T mutations were identified. These included: A:T----G:C transitions, transversions and frameshifts. The relative contribution of these events was found also to decrease with increasing dose. These results may help explain why the parent carcinogen N-nitroso-N,N-dimethylamine is hepatotropic while other methylating carcinogens, similarly metabolized in the liver, are not.

Base Composition↗
PubMed1992

Secondary amine precursors to nitrosamines in human saliva, gastric juice, blood, urine and faeces.

It has been suggested that the endogenous nitrosation of aliphatic, cyclic and heterocyclic secondary amines in the urinary bladder of patients with chronic urinary bacterial infections and in the human stomach may provide an important additional source of exposure to carcinogenic volatile N-nitrosamines. The most commonly occurring nitrosatable secondary amines found in human saliva, gastric juice, blood, urine and faeces are dimethylamine (DMA), pyrrolidine (PYR) and piperidine (PIP). All of 40 analysed samples of gastric juice contained 0.87 +/- 0.89 (SEM) microgram/ml DMA, 39 contained 1.35 +/- 2.53 microgram/ml PIP, 36 contained 0.18 +/- 0.15 microgram/ml PYR and 14 contained 0.05 +/- 0.11 microgram/ml diethylamine. Nitrate (14.0 +/- 15.7 microgram/ml) was present in all samples and 11 of 40 samples contained 0.43 +/- 1.38 microgram/ml nitrite. Only one gastric juice sample with pH less than 4.5 contained nitrite (0.1 microgram/ml). In paraplegics, patients with bladder augmentations and two control groups without bacterial infections of the urinary bladder, a mean daily excretion of 40.5-49.7 mg/day DMA, 19.4-23.8 mg/day PYR and 26.1-31.7 mg/day PIP was found. In both patient groups suffering from chronic bacterial infection of the urinary bladder, the corresponding volatile N-nitrosamines were formed by endogenous nitrosation and excreted in urine.

Bacteria↗