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PubMed1991

Inhibition of herpes simplex virus types 1 and 2 replication in vitro by mercurithio analogs of deoxyuridine.

The in vitro antiviral activity of several 5-mercurithio analogs of 2'-deoxyuridine (dUrd) on the replication of herpes simplex virus types 1 (HSV-1) and 2 (HSV-2) were examined. Of those compounds tested, the thioglycerol analog of 5-mercuri-2'-deoxyuridine (HgdUrd) was most effective in inhibiting the replication of HSV-1 in KB cells with a 50% inhibitory dose (ID50) of 0.001 micrograms/ml while the glutathione analog of HgdUrd was the most effective in inhibiting the replication of HSV-2 with a ID50 of 0.075 micrograms/ml. Conversely in HeLa TK- cells, the mercaptoguanosine analog of HgdUrd was the most effective compound in inhibiting virus replication with ID50S of 0.098 and 0.001 micrograms/ml for HSV-1 and HSV-2 respectively. These results suggest that these mercurithio analogs of dUrd are as effective as acyclovir in preventing the replication of these herpesviruses.

Antiviral Agents↗
PubMed1983

Neurotransmitter receptors as targets for pesticides.

Nicotinic and muscarinic acetylcholine (ACh) receptors have been identified biochemically by means of their specific binding of [3H] alpha-bungarotoxin ([3H]alpha-BGT) and [3H]quinuclidinyl benzilate, respectively. There are some differences in the drug specificities, and sensitivities to active group reagents, of these receptors in insects when compared to those in vertebrates. Also, insect brain contains more nicotinic than muscarinic receptors, while the reverse is found in mammalian brain. Insect brain contains a third kind of putative ACh-receptor that is relatively soluble and is both nicotinic and muscarinic in its pharmacology but does not bind alpha-BGT. Toxic nicotine and analogs bind to it with high affinities. Several organophosphorus and carbamate insecticides and nereistoxin bind with high affinities to the nicotinic ACh-receptor of the electric organ of Torpedo. A few chlorinated hydrocarbon insecticides and derivatives interact with Torpedo nicotinic ACh-receptors, not at their 'receptor' sites but at their allosteric or 'channel' sites (which are identified by their specific binding of [3H]perhydrohistrionicotoxin). A few also bind to mammalian brain muscarinic receptors. The most potent on both receptors is the acaricide chlorobenzilate. Pyrethrins and synthetic pyrethroids also bind with high affinities to the channel sites of the Torpedo nicotinic ACh-receptor, though not to its receptor sites. Another group that binds to ACh-receptors is the organic and inorganic mercury compounds, which interact with both the Torpedo nicotinic and rat brain muscarinic receptors. Thus, neurotransmitter receptors act as molecular targets, primary or secondary for different pesticides.

Acetylcholinesterase↗
PubMed1985

The octanol/water distribution of mercury compounds.

Lipophilicity plays an important role in the biological action of mercurials. The distribution of one inorganic and five organic mercury compounds was determined in an n-octanol/water system. Lipophilicity decreased in the order CH3HgCl, bromomercurihydroxypropane, HgCl2, chlormerodrin, p-chloromercuribenzoic acid (PCMB), p-chloromercuriphenylsulfonic acid (PCMBS). The toxicity of mercurials, as reported in the literature, appears to parallel their lipophilicity.

Chemical Phenomena↗
PubMed1977

Clinical toxicology of mercury.

Based on an extensive literature search, general principles of mercury toxicity are outlined with respect to human individuals and populations. For the metal itself, as well as for its most important inorganic and organic compounds, the review discussed behavior in the body, characteristic clinical pictures, assessment of threshold levels, and evaluation as potential environmental hazards. Particular emphasis is placed on those diagnostic signs and symptoms which furnish early warning signals, permitting detection and elimination of overexposures.

Epidemiologic Methods↗
PubMed1976

Differential effects of nephrotoxic agents on renal transport and metabolism by use of in vitro techniques.

A number of studies by the author and other investigators are reviewed in which the in vitro kidney slice technique has been used to evaluate the nephrotoxicity of various compounds. The kidney slice technique can be used to determine the effect of prior drug treatment of laboratory animals on renal organic acid (p-aminohippurate) or organic base (N-methylnicotinamide) transport, on glucose synthesis, and on oxygen consumption by renal coritical slices. The nephrotoxic agents uranyl nitrate and potassium dichromate exert inhibitory effects on renal function, althouhg both agents enhance organic base transport at low doses and potassium dichromate enhances organic acid transport at moderate doses. Enhanced PAH transport has been found to be a sensitive indicator of gentamicin induced nephrotoxicity, while inhibition of other parameters has been reported. The tissue slice method is less effective in evaluation chronic nephrotoxicity such as that produced by lead. The inhibitory effect of mercurial diuretics has been shown to be due to the general depression of metabolic activity by mercury. The kidney slice technique has been found to be a sensitive indicator in the assessment of halogenated hydrocarbon-induced nephrotoxicity. Differential effects of compounds on in vitro organic acid and base trasport provides information about the transport of these compounds as well as about their nephrotoxicity. Although it is often desirable to perform in vivo tests or other in vitro renal function tests, the kidney slice technique has proved to be extremely useful in toxicological evaluations.

Animals↗
PubMedDate not supplied

Effect of mersalyl at cholinoceptive sites.

The effects of an organic mercurial compounds, mersalyl, were tested at the muscarinic and nicotinic sites (the smooth muscles, frog heart and frog rectus muscle) in vitro. Mersalyl had an antimuscarinic effect in the smooth muscle tissues and in the myocardium. On the frog rectus muscle, mersalyl had some potentiating effect on acetylcholine response.

Animals↗
PubMed2006

Assembly of a new family of mercury(II) zwitterionic thiolate complexes from a preformed compound [Hg(Tab)2](PF6)2 [Tab = 4-(trimethylammonio)benzenethiolate].

Reactions of Hg(OAc)2 with 2 equiv of TabHPF6 [TabH = 4-(trimethylammonio)benzenethiol] in MeCN/MeOH afforded a mononuclear linear complex [Hg(Tab)2](PF6)2 (1). By using 1 as a precursor, a new family of mercury(II) zwitterionic thiolate complexes, [Hg2(Tab)6](PF6)4.2MeCN (2.2MeCN), [Hg(Tab)2(SCN)](PF6) (3), [Hg(Tab)2(SCN)2] (4), [Hg(Tab)I2] (5), {[Hg(Tab)2]4[HgI2][Hg2I6]}(PF6)2(NO3)4 (6), [Hg(Tab)2][HgI4] (7), [Hg(Tab)2][HgCl2(SCN)2] (8), [Tab-Tab]2[Hg3Cl10] (9), and [Hg2(Tab)6]3(PF6)Cl11 (10), were prepared and characterized by elemental analysis, IR spectra, UV-vis spectra, 1H NMR, and single-crystal X-ray crystallography. The [Hg2(Tab)6]4+ tetracation of 2 or 10 contains an asymmetrical Hg2S2 rhomb with an inversion center lying on the midpoint of the Hg...Hg line. The Hg atom of the [Hg(Tab)2]2+ dication of 3 is coordinated to one SCN-, forming a rare T-shaped coordination geometry, while in 4, the Hg atom of [Hg(Tab)2]2+ is coordinated to two SCN-, forming a seesaw-shaped coordination geometry. Through weak secondary Hg...S coordinations, each cation in 3 is further linked to afford a one-dimensional zigzag chain. The trigonal [Hg(Tab)I2] molecules in 5 are held together by weak secondary Hg...I and Hg...S interactions, forming a one-dimensional chain structure. In 6, the four [Hg(Tab)2]2+ dications, one HgI2 molecule, one [Hg2I6]2- dianion, one PF6-, and four NO3- anions are interconnected by complicated secondary Hg...I and Hg...O interactions, forming a scolopendra-like chain structure. The secondary Hg...I interactions, [Hg(Tab)2]2+ and [HgI4]2- in 7, are combined to generate a one-dimensional chain structure, while [Hg(Tab)2]2+ and [HgCl2(SCN)2]2- in 8 are interconnected by secondary Hg...N interactions to form a one-dimensional zigzag chain structure. Compound 9 consists of two [Tab-Tab]2+ dications and one [Hg3Cl10]4- tetraanion. The facile approach to the construction of 2-8 and 10 from 1 may be applicable to the mimicking of a coordination sphere of the Hg sites of metallothioneins.

Crystallography, X-Ray↗
PubMed1976

[The resistance of "Pseudomonas" to antibiotics and heavy metal: minimal inhibitory concentrations and genetic transfers (author's transl)].

The antibiotic sensitivity of 43 strains of Pseudomonas and the minimal inhibitory concentration of mercurial derivatives (5 mineral salts and 4 organics compounds) and of silver nitrate to these microorganisms have been studied. Twelve of these strains were P. aeruginosa of hospital origin, and 31 were Pseudomonas from surface water. Resistance against these inhibitory substances let us to established some connections between the different strains. Some strains were selected to transfer resistance markers by conjugation.

Anti-Bacterial Agents↗
PubMed1988

Fluorescein mercuric acetate as a dye for fluorescence and electron microscope detection of -SH groups in mouse sperm protamines: a critical evaluation.

Fluorescein Mercuric Acetate (FMA), a specific fluorescent dye for thiols, was tested as a possible reagent for the ultrastructural detection of -SH groups in sperm chromatin protamines. It was shown that FMA may be profitably used for staining at electron microscopy the chromatin -SH groups of caput epididymidis spermatozoa. Like other mercury compounds, FMA proved to be unstable under the electron beam; therefore the use of low beam intensity, and cooling of the specimens are recommended. The main advantages of this staining method are the relatively lower toxicity of FMA, compared to other organic mercurials, and the opportunity to compare the fluorescence patterns on semithin sections with the corresponding ultrastructural findings on thin sections.

Animals↗
PubMed1984

Reduction of organic mercury in water, urine, and blood by sodium borohydride for direct determination of total mercury content.

We have established the optimal conditions for use of sodium borohydride as the reducing agent before the direct determination of mercury in water, urine, and blood by atomic absorption spectroscopy. We evaluated the effects of pH, temperature, and cupric sulfate concentration on the direct determination of both organic and inorganic compounds of mercury. Accurate and precise quantification of mercury requires that the pH be between 9.3 and 9.5, the reaction temperature above 25 degrees C, the reaction time longer than 1 min, and, for urine samples only, the cupric sulfate concentration 10 mumol/L. The detection limit of the method is 1 to 2 ng and the precision (CV) is 3.8% for blood and 4.0% for urine.

Borohydrides↗
PubMedDate not supplied

[Fertility of workers exposed to herbicides and pesticides].

Twenty-one workmen exposed to herbicide as organic mercury compounds and to pesticide as halogenic hydrocarbon has been investigated concerning their fertility. If the concentrations of organic mercury compounds increase in the air of the place of employment then the levels of this heavy metal are also higher in the urine and in the ejaculate, and the fertility is reduced. It could also be established that a correlation exists between the concentration of pesticide in the place of employment and the male fertility, especially in cases with an excess of maximum permitted concentrations.

Adult↗
PubMed1974

Mercury(II) binding to s4U in E. coli tRNA(Val).

The accessibility of the s(4)U base in native tRNA(Val) from E.coli was monitored by studying the binding of various mercurials. The relative binding order HgBr(2)[unk]HgCl(2)>>CH(3)HgOAc[unk]CH(3)HgCl[unk]PCMB parallels approximately the steric requirements of linear HgX(2) or RHgX compounds for S(N)2 displacement by sulfur, although other factors are operative. Para-chloromercuri-benzoate (PCMB) does not bind the thiolated nucleotide unless the tertiary structure of the tRNA is opened up by removal of Mg(2+) ions and heating to 40 degrees . Under these conditions, equilibrium dialysis measurements using (14)C-labeled PCMB showed one binding site (n = 0.93) with an association constant, K(1), of 9 x 10(4)M(-1).

Binding Sites↗
PubMed1984

Relation between red cell anion exchange and water transport.

A new distilbene compound, 4',4'-dichloromercuric-2,2,2',2'-bistilbene tetrasulfonic acid (DCMBT), has been synthesized for use in studies of anion and water transport in the human red cell. DCMBT combines features of both the specific stilbene anion transport inhibitor, DIDS, and the mercurial water transport inhibitor, pCMBS. This new compound inhibits anion transport almost completely with a Ki of 15 microM. DCMBT also inhibits water transport by about 15-20% with a Ki of about 8 microM. Treatment of red cells with DIDS inhibits the effect of DCMBT on water transport, suggesting that anion transport and water transport are mediated by the same protein.

4,4'-Diisothiocyanostilbene-2,2'-Disulfonic Acid↗
PubMed1993

Determination of sulfhydryl groups in ovalbumin by high-performance liquid chromatography with inductively coupled plasma mass spectrometric detection.

High-performance liquid chromatography (HPLC) interface to inductively coupled plasma mass spectrometry (ICPMS) has been applied for the first time to determine the sulfhydryl groups (SHs) in chicken ovalbumin (OVA) after their conversion into mercaptides with organic mercury compounds. The procedure is based on the HPLC separation of mercury mercaptide OVA followed by ICPMS detection of mercury. The rates of reaction of five mercaptide-forming reagents with SHs in OVA were in the order ethylmercuric chloride > mersalyl acid > p-chloromercuribenzoate > p-(chloromercuri)benzenesulfonic acid > fluorescein mercuric acetate. Apparently the reaction rate is slowed by an increase in the steric hindrance around the mercury atom. The detection limit for SHs was lower than 1 pmol of OVA.

Animals↗
PubMed1984

Effects of analogs of salicylate on p-aminohippurate uptake into basal-lateral membranous vesicles.

In basal-lateral membranes of the renal cortex, thiol substituted analogs of salicylate inhibited the uptake of p-aminohippurate (PAH). The mercury-containing analogs, thimerosal and mercaptide V (formed from 2 mol of thiosalicylate and 1 mol of Hg++), were highly inhibitory. Compared with probenecid, thimerosal and mercaptide V yielded dose-response curves of steeper slope and higher maximal effect. The dose-response curves of thimerosal and mercaptide V were similar in shape, although mercaptide V was more potent. The inhibition by thimerosal, mercaptide V and mersalyl acid, an anionic sulfhydryl reagent which also inhibits uptake of PAH ( Tse et al., J. Pharmacol. Exp. Ther. 226: 19-26, 1983), was found to be competitive with Ki values of 0.39 +/- 0.05, 0.12 +/- 0.06 and 0.05 +/- 0.02 mM, respectively. The inhibitory effects of thimerosal and mercaptide V were only partially reversible. Thimerosal and mercaptide V reacted 35 and 62%, respectively, with membrane sulfhydryl groups which may explain the nonreversibility of the inhibitor. The nonreversibility is probably not due to irreversible destruction of the vesicles, as the "glucose space" of the vesicles was not affected by these two compounds. That derivatives of salicylates capable of reacting with sulfhydryl groups were more inhibitory than thiosalicylate is consistent with a hypothesis that the PAH transporter contains a sulfhydryl group(s) essential for uptake. Based on the degree of inhibition, the degree of reversibility, the degree of membrane sulfhydryl group oxidation and the computer-generated three dimensional models of thimerosal, mercaptide V and mersalyl acid, a model of the PAH transporter is proposed.

Aminohippuric Acids↗
PubMed1987

[Reaction of fluorescein bimercuric acetate with a molybdenum center of xanthine oxidase from milk].

Inhibition of milk xanthine oxidase by fluorescein bimercuriacetate (FMA) allows for the classification of S-containing groups according to their localization and role in the catalytic activity of the enzyme. The enzyme (E) complexes with FMA (E--FMA I and E--FMA II) differing in their activity, stoichiometry and spectral properties were studied at various experimental conditions, reaction time and FMA concentrations. The enzyme molecule contains 5 groups that are reactive towards FMA (E--FMA I) and are localized outside the active center. That these groups have no concern with activity and are subjected to modification irrespective of whether or not the xanthine oxidase molecule has an intact Mo-center. The formation of an inactive E--FMA II complex is associated with an additional (in comparison with E--FMA I) binding of two FMA molecules per molecule of the active enzyme. The stoichiometry of the E--FMA II complex was determined by the X-ray fluorescent method from the amount of the Hg in enzyme. A kinetic scheme of xanthine oxidase inhibition by FMA is proposed, according to which the inhibition is a result of modification of two groups in the enzyme active center, of which only one is essential for the enzyme activity. This scheme also postulates the role of reversible E--FMA complexes in the course of irreversible inhibition. Xanthine oxidase is protected against FMA by the substrate (xanthine), competitive inhibitors (azaxanthine and allopurinol) and acceptor (2,6-dichlorophenolindophenol), i. e., compounds which interact with the Mo-center of the enzyme. The EPR spectra of the dithionite-reduced E--FMA II complex were found to contain a "slow" signal, Mo(V), typical of the Mo-center devoid of labile sulphur. It was assumed that the essential group interacting with FMA in the active center of xanthine oxidase as a terminal sulphur which is a component of the coordination region of Mo.

Animals↗
PubMed1985

A rapid and sensitive high-performance liquid chromatographic assay for 6-mercaptopurine metabolites in red blood cells.

A highly sensitive and rapid assay for the detection of 6-mercaptopurine metabolites in the red blood cells of leukemic patients receiving the drug has been developed. The method employs a batch-chromatographic procedure using a mercurial cellulose resin to selectively absorb thiol compounds combined with separation by high-performance liquid chromatography using a Partisil-SAX column and uv detection. This method permits detection of 6-thioinosine monophosphate, 6-thiouric acid, and 6-thioguanosine mono-, di-, and triphosphates in patient samples with a sensitivity of 5-10 pmol. No 6-thioinosine di- or triphosphates were detected in patient samples. The results of our study indicate that 6-thioguanosine triphosphate is the major metabolite of 6-mercaptopurine retained by red blood cells after oral or iv administration of the drug.

Biotransformation↗