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PubMed1993

[DNA methylation of monohalogenated methanes of F344 rats].

Monohalogenated methanes (methyl chloride, methyl bromide and methyl iodide) are mutagenic and carcinogenic. The possible mechanism of these effects, DNA methylation, was studied. DNA adducts from organs of F344 rats exposed to these chemicals were separated and identified with high performance liquid chromatography (HPLC) and gas-chromatography/mass-spectrometry (GC/MS). DNA adducts, 7-methylguanine (7-MeG) and O6-Methylguanine(0(6)-MeG), incorporation of 14C into de novo synthesis of nucleobases could be observed in enzymatic DNA hydrolysates by HPLC and determination of the radioactivity in the fractions. The formation of DNA adducts in the studied organs was only quantitatively different. The formation of O6-MeG was further proved by analysing the acidic hydrolysates using HPLC with non-radioactive O6-MeG as internal standard. 7-MeG and 3-MeA were identified with GC/MS analysis.

Animals↗
PubMedDate not supplied

Effect of 1.1.1 trifluoro-N-(2-methyl-4-phenyl sulfonyl) methane sulfonamide (Destun 50WP) on rat hepatic microsomal enzymes, aniline hydroxylase and amino-pyrine N-demethylase.

Investigations have been carried out to determine the effects of the herbicide 1.1.1 trifluoro-N-(2-methyl-4-phenyl sulfonyl) methane sulfonamide (Destun) on some hepatic microsomal drug metabolizing enzymes in rat. Administration of 100 mg herbicide/kg rat (i.p. or oral) resulted in a stimulation of aniline hydroxylase and p-aminopyrene N-demethylase activities by 1.3 fold and 1.6 fold respectively. A dose-related increase in enzyme activities was observed with a maximum effect at about 100 mg Destun/kg rat. The increased microsomal protein content, liver weight: body weight ratio and decreased sleeping time in the herbicide-treated animals indicated the possibility of Destun being an "inducer". Results of investigations on the kinetic properties of aniline hydroxylase and p-aminopyrene-N-demethylase on administration of Destun suggests that in addition to its inducer effect, the herbicide could stimulate the enzyme activities by decreasing the affinity of these enzymes for their respective substrates.

Aminopyrine N-Demethylase↗
PubMed2002

Critical analysis of biomonitoring endpoints for measuring exposure to polymeric diphenyl-methane-4,4'-diisocyanate (MDI) in rats: a comparison of markers of exposure and markers of effect.

The object of this study was to compare the relative sensitivity of markers of exposure and effects in the lung of rats exposed to polymeric diphenyl-methane-4,4'-diisocyanate (pMDI) aerosol. Rats were repeatedly exposed to 12.9 mg pMDI/m(3) (6 h/day, 5 days/week for 14 days; exposure was from days 0--17 followed by a post-exposure period to day 35). Markers of exposure were determined in bronchoalveolar lavage (BAL), blood (haemoglobin, plasma proteins), and urine on days 1, 4, 11, 18, 21, 28 and 35. Markers of effects were determined at the same time points and focused on changes in BAL constituents. In BAL, a maximum increase of total protein occurred following the first exposure and levelled off subsequently whilst BAL cell-related endpoints increased in a time-dependent manner. The kinetics of formation and elimination of adducts differed appreciably from one dosimeter to another. Whilst haemoglobin adducts were integrated by the cumulative exposures, the incremental yield of adduct formation appeared to be dependent on pulmonary as well as yet unknown erythrocyte-related factors. Plasma protein adducts attained a plateau after 1 week of exposure. MDI-related metabolite levels in urine did not show any time-dependent changes during the entire exposure period and declined rapidly during the post-exposure period. Thus, the kinetics of the fractional loading and clearance of pulmonary and extrapulmonary dosimeters did not parallel each other, nor was there a clear correlation with the markers of effects. In summary, it is concluded that biomonitoring is a powerful tool for the comparative dosimetry of well-defined exposure regimens. However, especially for irritant agents demonstrating portal-of-entry effects, markers related to 'total body burden' may not necessarily predict the absence or presence of local responses occurring within the target organ, namely the lung. In all compartments, dosimeters related to higher oligomers of MDI demonstrated low bioavailability, i.e. their recovery was appreciably lower than expected.

Administration, Inhalation↗
PubMed2004

Occurrence of PCBs, organochlorine insecticides, tris(4-chlorophenyl)methane, and tris(4-chlorophenyl)methanol in human breast milk collected from Cambodia.

The present study determined the concentrations of persistent organochlorines (OCs) such as DDT and its metabolites (DDTs), polychlorinated biphenyls (PCBs), hexachlorocyclohexane isomers (HCHs), hexachlorobenzene (HCB), chlordane compounds (CHLs), tris(4-chlorophenyl)methane (TCPMe), and tris(4-chlorophenyl)methanol (TCPMOH) in human breast milk from Cambodia. DDTs, PCBs, HCHs, HCB, CHLs, and TCPMe were detected in almost all the human breast milk samples analyzed, and the concentrations ranged from 310 to 11,000, 6.0 to 87, <0.12 to 21, <0.12 to 8.1, <0.12 to 5.3, and 2.9 to 70 ng/g lipid wt, respectively. TCPMOH was detected in only 10 among 36 samples. Concentrations of DDTs in human breast milk from Cambodia were notably higher than those from developed countries and comparable to those from other developing countries, where usage of DDT for agricultural and public health purposes has been suspected to be continuing still, implying the recent usage of DDT in Cambodia. On the other hand, concentrations of PCBs, HCHs, HCB, and CHLs in human breast milk from Cambodia were 1-2 orders of magnitude less than those from other countries, indicating that Cambodia is one of the less contaminated countries by these OCs. Significant correlation between concentrations of TCPMe and DDTs in human breast milk suggested that exposure to DDT is the source of TCPMe in Cambodian residents. Concentrations of OCs in human breast milk tended to decrease with an increase in the number of children, implying that the first infant would be exposed to higher levels of OCs from breast milk and might be at higher risk by these contaminants, especially DDTs in Cambodia. To our knowledge, this is the first comprehensive study on the residue levels of OCs in human breast milk from Cambodia.

Adolescent↗
PubMed2002

A rapid fluorescence-based assay for detecting soluble methane monooxygenase.

A fluorescence-based assay was developed to estimate soluble methane monooxygenase (sMMO) activity in solution. Whole cells of Methylosinus trichosporium OB3b expressing sMMO were used to oxidize various compounds to screen for fluorescent products. Of the 12 compounds tested, only coumarin yielded a fluorescent product. The UV absorbance spectrum of the product matches that of 7-hydroxycoumarin, and this identification was confirmed by 13C-NMR spectroscopy. The dependence of the fluorescent reaction on sMMO activity was investigated by pre-incubation with acetylene, a known inhibitor of sMMO activity. Apparent kinetic parameters for whole cells were determined to be Km(app)=262 microM and Vmax(app)=821 nmol 7-hydroxycoumarin min(-1) mg protein(-1). The rate of coumarin oxidation by sMMO correlates well with those of trichloroethylene degradation and naphthalene oxidation. Advantages of the fluorescence-based coumarin oxidation assay over the naphthalene oxidation assay include a more stable product, direct detection of the product without additional reagents, and greater speed and convenience.

Coumarins↗
PubMed2006

Isotopic evidence for methane-based chemosynthesis in the Upper Floridan aquifer food web.

Anecdotal observations of the Dougherty plain cave crayfish (Cambarus cryptodytes), the Georgia blind cave salamander (Haideotriton wallacei), and albinistic isopods (Caecidotea sp.) at great depths below the land surface and distant from river corridors suggest that obligate aquifer-dwelling (troglobitic) organisms are widely distributed throughout the limestone Upper Floridan aquifer (UFA). One mechanism by which subterranean life can proliferate in an environment void of plant productivity is through a microbial food web that includes chemosynthesis. We examined this possibility in the UFA by measuring the isotopic composition ((13)C, (14)C, and (15)N) of tissues from troglobitic macrofauna. Organisms that were captured by cave divers entering into spring conduits had delta(13)C values that suggested plant matter as a primary food resource (cave crayfish, -24.6 +/- 2.7 per thousand, n = 9). In contrast, delta(13)C values were significantly depleted in organisms retrieved from wells drilled into areas of the UFA remote from spring and sinkhole conduits (cave crayfish -34.7 +/- 9.8 per thousand, n = 10). Depleted (13)C values in crayfish were correlated with radiocarbon (Delta(14)C) depletion relative to modern values. The results suggest that methane-based microbial chemosynthetic pathways support organisms living in the remote interior of the aquifer, at least in part.

Alabama↗
PubMed2002

Density functional and electrostatics study of oxidized and reduced ribonucleotide reductase; comparisons with methane monooxygenase.

A combined broken symmetry density functional and electrostatics approach has been used to examine the active sites of the resting (RNR(ox)) and reduced (RNR(red)) forms of class I type ribonucleotide reductase in the protein and solvent environment. Active site cluster geometries and Heisenberg J values are discussed in the context of the available protein data. The total electrostatic interaction energy in the protein comprises a large reaction field component and a much smaller protein field term, the former suggesting strong dielectric polarization between the cluster and protein-solvent dielectrics; the latter is indicative of a very weak link to the protein environment. Decomposition of the protein field term elucidates the major electrostatic interactions between amino acid residues in the RNR R2 local environment and the active site cluster, enabling an energetic comparison of structurally equivalent residues with a related diiron protein, methane monooxygenase.

Binding Sites↗
PubMed2001

O-O bond cleavage and alkane hydroxylation in methane monooxygenase.

Several new aspects of the O-O bond cleavage and alkane hydroxylation mechanisms have been studied by hybrid density functional theory in this reinvestigation of methane monooxygenase. As concerning key intermediates in these reactions, a new important low-lying state is found, described either as Fe2(III,V) or as Fe2(III,IV)O. A fully optimized transition state for O-O bond cleavage has been determined. It is suggested that the large difference in optimal size (as determined in gas phase) of the complex, before and after the O-O bond cleavage, leads to an additional driving force for the reaction, not considered previously. The strain of the enzyme is estimated to lead to a driving force in the forward direction of about 5 kcal/mol, which could explain some of the pH dependence found in recent experiments. For the hydroxylation reaction, a clean hydrogen abstraction transition state leading to a substrate radical is again found, in contrast to interpretations of radical clock experiments. An explanation, based on new results, is suggested that could account for both the experimental and theoretical results.

Alkanes↗
PubMed2001

Desaturation reactions catalyzed by soluble methane monooxygenase.

Soluble methane monooxygenase (MMO) is shown to be capable of catalyzing desaturation reactions in addition to the usual hydroxylation and epoxidation reactions. Dehydrogenated products are generated from MMO-catalyzed oxidation of certain substrates including ethylbenzene and cyclohexadienes. In the reaction of ethylbenzene, desaturation of ethyl C-H occurred along with the conventional hydroxvlations of ethyl and phenyl C-Hs. As a result, styrene is formed together with ethylphenols and phenylethanols. Similarly, when 1,3- and 1,4-cyclohexadienes were used as substrates, benzene was detected as a product in addition to the corresponding alcohols and epoxides. In all cases, reaction conditions were found to significantly affect the distribution among the different products. This new activity of MMO is postulated to be associated with the chemical properties of the substrates rather than fundamental changes in the nature of the oxygen and C-H activation chemistries. The formation of the desaturated products is rationalized by formation of a substrate cationic intermediate, possibly via a radical precursor. The cationic species is then proposed to partition between recombination (alcohol formation) and elimination (alkene production) pathways. This novel function of MMO indicates close mechanistic kinship between the hydroxylation and desaturation reactions catalyzed by the nonheme diiron clusters.

Benzene Derivatives↗
PubMed2004

Molecular analysis of deep-sea hydrothermal vent aerobic methanotrophs by targeting genes of 16S rRNA and particulate methane monooxygenase.

Molecular diversity of deep-sea hydrothermal vent aerobic methanotrophs was studied using both 16S ribosomalDNA and pmoA encoding the subunit A of particulate methane monooxygenase (pMOA). Hydrothermal vent plume and chimney samples were collected from back-arc vent at Mid-Okinawa Trough (MOT), Japan, and the Trans-Atlantic Geotraverse (TAG) site along Mid-Atlantic Ridge, respectively. The target genes were amplified by polymerase chain reaction from the bulk DNA using specific primers and cloned. Fifty clones from each clone library were directly sequenced. The 16S rDNA sequences were grouped into 3 operational taxonomic units (OTUs), 2 from MOT and 1 from TAG. Two OTUs (1 MOT and 1 TAG) were located within the branch of type I methanotrophic ?-Proteobacteria. Another MOT OTU formed a unique phylogenetic lineage related to type I methanotrophs. Direct sequencing of 50 clones each from the MOT and TAG samples yielded 17 and 4 operational pmoA units (OPUs), respectively. The phylogenetic tree based on the pMOA amino acid sequences deduced from OPUs formed diverse phylogenetic lineages within the branch of type I methanotrophs, except for the OPU MOT-pmoA-8 related to type X methanotrophs. The deduced pMOA topologies were similar to those of all known pMOA, which may suggest that the pmoA gene is conserved through evolution. Neither the 16S rDNA nor pmoA molecular analysis could detect type II methanotrophs, which suggests the absence of type II methanotrophs in the collected vent samples.

Animals↗
PubMed1984

Purification of component A of the soluble methane monooxygenase of Methylococcus capsulatus (Bath) by high-pressure gel permeation chromatography.

A major improvement in the purification of the oxygenase protein (component A) of the methane monooxygenase has been effected. By employing high-pressure gel permeation chromatography several purification steps may be omitted from the previously published scheme. Furthermore the yield of the protein is enhanced and more importantly the recovered protein displays an increased specific activity, unlike that purified by other techniques.

Bacterial Proteins↗
PubMed1985

Isolation and characterization of a novel coenzyme Q from some methane-oxidizing bacteria.

The respiratory quinone composition of 18 strains of obligate methane-utilizing bacteria was examined. All of the strains contained lipoquinones which on examination by tlc co-chromatographed with coenzyme Q. On the basis of chromatographic and physicochemical analyses the lipoquinones produced by 10 of the strains corresponded to Q-8. Reverse-phase partition and argentation hplc demonstrated the quinone produced by the remaining 8 strains did not correspond to any known coenzyme Q prenologue. On the basis of mass spectrometry, 1H and 13C nuclear magnetic resonance spectrometry the novel quinone was shown to correspond to 2,3-dimethoxy-5-methyl-6-(18-methylene-3,7, 11,15,19,23,27,31-octamethyldotriacontahepta-2,6,10,14,22,26,30 enyl-)-1, 4-benzoquinone.

Chemical Phenomena↗
PubMed1988

Purification of a high specific activity methane monooxygenase hydroxylase component from a type II methanotroph.

The purification of the hydroxylase component of a 3 component methane monooxygenase from the type II methanotroph Methylosinus trichosporium OB3b is reported. The enzyme (240 kDa) has an (alpha beta gamma)2 subunit structure as observed for hydroxylases isolated from other Type I and Type II methanotrophs, but it exhibits a 5 to 10 fold higher specific activity and is isolated in 2 to 10 fold higher yield. EPR and Mössbauer spectra of the hydroxylase show that it contains a coupled iron center containing an even number of iron atoms. The spectra are similar to those of proteins known to contain oxo-bridged binuclear iron centers. The presence of such a center is unprecedented in a monooxygenase and suggests that a novel mechanism is utilized.

Chromatography, Gel↗
PubMed1981

Effect of N-methylpyridinium-2-aldoxime methane sulphonate (P2S) on rat intestinal, (Na-K)ATPase and adenyl cyclase activities.

The effect of N-methylpyridinium-2-aldoxime methane sulphonate (P2S), a drug recommended for prophylactic and therapeutic purposes in organophosphate poisoning, on intestinal (Na-K) ATPase and adenyl cyclase activities, was tested in rats. Intestinal (Na-K) ATPase activity was determined 5 h after intragastric administration of either 0.15 M NaCl or P2S 200 mg/kg body weight. P2S decreased significantly jejunal and colonic (Na-K)ATPase activity, 17.1 +/- 4.8 (S.E.) and 13.5 +/- 3.0, as compared to that in saline-treated rats, 41.5 +/- 3.0 (S.E.) and 25.4 +/- 1.2 mumol Pi/mg protein per h, respectively. Pretreatment with methyl prednisolone did not prevent the decrease in enzyme activity induced by P2S. Mucosal PGE2 and cAMP contents, adenyl cyclase and phosphodiesterase activities, were similar in P2S and saline-treated rats. It is thus suggested that P2S-induced inhibition of intestinal (Na-K)ATPase activity might be among the mechanisms contributing to looseness of the stool frequently observed following P2S administration.

Adenylyl Cyclases↗
PubMed1988

Antagonism by N-methyl levallorphan-methane sulphonate (SR 58002 C) of morphine-elicited acute and chronic central and peripheral effects.

The peripheral activity of the quaternary narcotic antagonist N-methyl levallorphan-methane sulphonate (SR 58002 C) at opioid sites located in the periphery and in the central nervous system (CNS), was studied by different approaches in rats after subcutaneous injection (s.c.). Pretreatment with SR 58002 C 2,8 or 32 mg/kg s.c. 10, 50 or 110 min before buprenorphine consistently reduced buprenorphine in vivo binding only in the small intestinal longitudinal muscle with attached myenteric plexus (MP), whereas naloxone (1 mg/kg s.c.) 10 min before buprenorphine lowered buprenorphine binding in MP and brain (without cerebellum). Plasma levels were not altered by SR 58002 C or naloxone. The same doses of SR 58002 C injected 10, 50 or 110 min before morphine selectively antagonized the inhibition of transit of a charcoal meal along the small intestine (mainly a peripheral effect) induced by the agonist, but did not antagonize morphine-elicited analgesia in the hot-plate test (central effect). Naloxone (1 mg/kg s.c.) injected 10 min before morphine antagonized both agonist effects simultaneously. In morphine-dependent rats SR 58002 C (0.25, 1, 4 and 32 mg/kg s.c.) induced diarrhea, dose-dependently, in most animals within the first 30 min, while jumping, measured in the same rats, occurred in some animals, not dose-dependently, from 60 min on. Naloxone (1 mg/kg s.c.) induced both effects in most rats. These findings suggest that, although SR 58002 C probably penetrates the blood-brain barrier in some morphine-dependent rats, it discriminates peripheral and CNS opioid effects.

Animals↗
PubMed1993

Intraperitoneal administration of leukotriene B4 (LTB4) and omega-guanidino caproic acid methane sulfonate (GCA) increased the survival of mice challenged with methicillin-resistant Staphylococcus aureus (MRSA).

Infections caused by methicillin-resistant Staphylococcus aureus (MRSA) very often complicate management of immunocompromised patients. We studied the effect of leukotriene B4 (LTB4) and epsilon-guanidino caproic acid methane sulfonate (GCA), on MRSA infection. Mice fed a 20% casein diet were intraperitoneally administered LTB4, GCA, or saline (control) daily for 30 days. On the 10th day of this treatment, mice were challenged with MRSA. The survival rate in the control group (20%) was significantly lower than the rates in the GCA (60%) and LTB4 (50%) groups, respectively (p < 0.05). There was a significant reduction of MRSA in the spleen and kidney of the survived mice in GCA group as against mice in the LTB4 and saline groups, indicating a better recovery in GCA group than the other groups. The results suggest that intraperitoneal administration of GCA and LTB4 may play a role in host defense mechanism during MRSA infections.

Animals↗
PubMed1990

No significant increase in spontaneous and ethyl methane sulfonate-induced sister chromatid exchanges at the Xq27.3 fragile site.

The present study was performed to determine if the fra(X)(q27.3) site is inherently a high sister chromatid exchange (SCE) site independent of fragility. Therefore, we studied baseline and ethyl methane sulfonate (EMS)-induced SCEs in peripheral blood lymphocytes from 10 retarded fragile-X male patients and eight retarded nonfragile-X male controls. The distributions of SCE scores per chromosome within each experimental condition showed significant interindividual variability in response to EMS treatment in the fragile-X group. Each fragile-X patient was therefore compared with a matched control. No significant differences were found in the distribution of SCE scores per chromosome. In addition, at the Xq27 site, whatever the degree of expressed fragility, no significant differences between fragile-X and control groups were evident in the spontaneous or EMS-induced SCEs. The fra(X)(q27.3) site therefore is not a hot spot for spontaneous or EMS-induced SCEs. Because fluorodeoxyuridine (FUdR) treatment has been shown to induce SCE at this site, our results indicate that the Xq27.3 site must be structurally different from other nonfragile SCE sites.

Cells, Cultured↗
PubMed1987

Antipicornavirus activity of some diaryl methanes and aralkylaminopyridines.

Sixteen diarylmethanes and ten aralkylaminopyridines were initially evaluated for their in vitro activity against rhinoviruses 1A, 2 and 64 and against coxsackievirus A21 and for their oral prophylactic and therapeutic activity in mice challenged with coxsackievirus A21. Based on these preliminary studies the diarylmethane (3,4-dichlorophenoxy)-(5 methylsulfonyl-2-pyridinyl)-methane and the aralkylaminopyridine (2-(3,4-dichlorobenzylamino)-5-methylsulfonylpyridine were compared with their oxygen bridged analogue 2-(3,4-dichlorophenoxy)-5-(methylsulfonyl)pyridine for in vitro activity against a larger number of picornaviruses and for their in vivo protective efficacy in dose response assays. All three compounds exhibit similar in vitro activity inhibiting 12 to 15 (52.2-65.3%) of the 23 picornaviruses tested at concentrations of less than 5.0 micrograms/ml. However, the aralkylaminopyridine was found to be the most active in vivo; significantly protecting coxsackievirus A21 challenged mice after a single oral dose of 37.5 mg/kg (P less than or equal to 0.05) and during a continuous oral dose regimen of as low as 18.8 mg/kg per day (P less than 0.01).

Aminopyridines↗