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PubMed1996

Structure of Dicopper Complexes of N,N,N',N'-Tetrakis[(2-benzimidazolyl)methyl]-2-hydroxy-1,3-diaminopropane with Coordinated Thiocyanate Counterions.

The structures of five dicopper complexes of binucleating ligand HL-H (N,N,N',N'-tetrakis[(2-benzimidazolyl)methyl]-2-hydroxy-1,3-diaminopropane) with thiocyanate and some other counterions were investigated by the X-ray diffraction method. In Cu(2)(HL-H)(NCS)(2)Cl(2).6H(2)O.CH(3)OH, 1 (a = 12.524(5) Å, b = 14.429(4) Å, c = 16.343(3) Å, alpha = 109.01(2) degrees, beta = 92.62(2) degrees, gamma = 115.27(3) degrees, Z = 2, triclinic, P&onemacr;), one chloride is not coordinated. Distorted square pyramidal (SP) geometry is found for both CuN(3)ClN and CuN(3)ON coordination sites in which the N(3) tripodal coordination sites come from the two symmetric halves of HL-H and the other nitrogen atoms come from thiocyanate ions. In Cu(2)(HL-H)(NCS)(2)(ClO(4))(2).6H(2)O.2EtOH, 2 (a = 10.955(2) Å, b = 15.366(5) Å, c = 18.465(9) Å, alpha = 65.57(4) degrees, beta = 89.73(3) degrees, gamma = 79.81(2) degrees, Z = 2, triclinic, P&onemacr;), the coordination environments for the two copper ions are both CuN(3)ON. However, their geometries are different: one is distorted SP and the other is distorted trigonal bipyramid (TBP). In Cu(2)(HL-H)(NCS)(2)(ClO(4))(2)Cl.H(3)O.3.5H(2)O, 3 (a = 11.986(6) Å, b = 12.778(5) Å, c = 17.81(1) Å, alpha = 82.41(4) degrees, beta = 75.44(5) degrees, gamma = 78.46(4) degrees, Z = 2, triclinic, P&onemacr;), the chloride ion does not coordinate to copper ion, but it is hydrogen bonded to the hydroxy hydrogen. The coordination environments for the two copper ions are both CuN(3)ON with distorted SP geometries. In Cu(2)(HL-H)(NCS)Cl(3).6H(2)O, 4 (a = 12.026(5) Å, b = 14.369(6) Å, c = 16.430(6) Å, alpha = 111.64(3) degrees, beta = 90.51(4) degrees, gamma = 113.90(3) degrees, Z = 2, triclinic, P&onemacr;), one chloride does not coordinate. The coordination environments for the two copper ions are CuN(3)ON in severely distorted TBP geometry and CuN(3)Cl(2) in SP geometry. In Cu(2)(HL-H)(NCS)(3)OH.2H(2)O.3CH(3)OH.Et(2)O, 5 (a = 18.322(5) Å, b = 15.543(6) Å, c = 19.428(7) Å, beta = 102.78(3) degrees, Z = 4, monoclinic, P2(1)/c), the hydroxide ion does not coordinate. The coordination environments for the two copper ions are CuN(3)N(2) with a geometry inbetween SP and TBP but slightly closer to SP and CuN(3)ON in distorted SP geometry. The distances between the copper ions are in the range 4.45-7.99 Å, indicating negligible interaction between the copper ions. The hydroxy groups of HL-H in 1-5all coordinate to copper ions either in a terminal mode (in complexes 1, 4, and 5, denoted as OHR(t)) or in a bridging mode (in complexes 2 and 3, denoted as OHR(b)). These hydroxy groups do not lose their protons in all cases. All thiocyanate anions coordinate to copper ions through nitrogen atoms. All copper ions in 1-5 are pentacoordinated. The fact that the CuN(3) geometries of the tripodal coordination sites in HL-H do not allow the formation of a square planar complex, may be the driving force for the formation of pentacoordinated complexes. From the structurally known dicopper complexes of the HL-H type ligands, the relative coordinating abilities of ligands to CuN(3) are OHR(t) > NCS(-) > Cl(-)(t) > OHR(b) approximately Cl(-)(b), where the letters b and t in parentheses denote bridging and terminal coordination modes respectively.

Journal Article↗
PubMed1999

Anisotropic Templating Effect in the Formation of Two-Dimensional Anionic Cadmium-Thiocyanate Coordination Solids [(12C4)(2)Cd][Cd(2)(SCN)(6)] and [(12C4)(2)Cd][Cd(3)(SCN)(8)] with Checkerboard and Herringbone Patterns, Respectively.

This paper reports the syntheses, characterization, and structures of two new two-dimensional cadmium-thiocyanate coordination solids [(12C4)(2)Cd][Cd(2)(SCN)(6)] (1) and [(12C4)(2)Cd][Cd(3)(SCN)(8)] (2), where 12C4 denotes 12-crown-4, C(8)H(16)O(4). 1 crystallizes in a monoclinic unit cell, space group C2/c with lattice parameters a = 16.297(3) Å, b = 26.267(3) Å, c = 16.296(2) Å, beta = 90.20(1) degrees, and Z = 8. 2 crystallizes in a monoclinic unit cell, space group P2(1)/n with lattice parameters a = 11.604(7) Å, b = 11.366(7) Å, c = 15.736(4) Å, beta = 92.84(3) degrees, and Z = 2. The structure of 1 exhibits a two-dimensional tetragonal motif consisting of Cd(2) units arranged in a checkerboard pattern with the dimeric [Cd(2)(SCN)(6)](2)(-) complex as the building block. The crystal structure of 2 can be described as a two-dimensional hexagonal array of linear trimeric Cd(3) units arranged in a herringbone pattern with the [Cd(3)(SCN)(8)](2)(-) complex as the building block. In both 1 and 2, the [(12C4)(2)Cd](2+) dications are housed in cavities within and between the anionic cadmium-thiocyanate layers but with different orientations ("upright" in 1 and "sideways" in 2) with respect to the cadmium-thiocyanate layers, giving rise to an anisotropic templating effect.

Journal Article↗
PubMed2003

Ambident reactivity of the thiocyanate anion revisited: can the product ratio be explained by the hard soft acid base principle?

Laser flash photolysis and stopped-flow methods have been employed to determine the kinetics of the reactions of benzhydrylium ions with both termini of the thiocyanate ion. In contrast to previous investigations which reported sulfur/nitrogen ratios of k(S)/k(N) = 2-10 for the reactions of carbocations with SCN(-), values of k(S)/k(N) = 10(3)-10(4) are now derived from absolute rate constants. This discrepancy is explained by the fact that the data determined in this investigation are the first which refer to activation-controlled attack of carbocations at both termini of the thiocyanate ion, while previous reactivity ratios included diffusion-controlled reactions. It is concluded that the selectivities of the reactions of carbocations with the thiocyanate ion cannot be explained by the hard soft acid base principle.

Journal Article↗
PubMed2005

A novel three-dimensional copper(II) coordination polymer with 1,4-bis(1,2,4-triazol-1-ylmethyl)benzene and thiocyanate.

In the title complex, poly[copper(II)-di-2-thiocyanato-2-1,4-bis(1,2,4-triazol-1-ylmethyl)benzene], [Cu(NCS)2(C12H12N6)]n, the CuII atom lies on an inversion centre in a tetragonally distorted octahedral environment. Four N atoms from thiocyanate and 1,4-bis(1,2,4-triazol-1-ylmethyl)benzene (bbtz) ligands fill the equatorial positions, and S atoms from symmetry-related thiocyanate ligands fill the axial positions. The benzene ring of the bbtz ligand lies about an inversion centre. Single thiocyanate bridges link the CuII atoms into two-dimensional sheets containing an unprecedented 16-membered [Cu4(-NCS-N:S)4] ring. The bbtz ligands further link the two-dimensional sheets into a three-dimensional network.

Journal Article↗
PubMed2005

A novel thiocyanate-bridged dinuclear cadmium(II) complex: di-mu-thiocyanato-bis((methanol){4-nitro-2-[2-(dimethylamino)ethyliminomethyl]phenolato}cadmium(II)).

The title complex, [Cd2(C11H14N3O3)2(NCS)2(CH4O)2], is an interesting thiocyanate-bridged dinuclear cadmium(II) compound. It is located on a crystallographic inversion center. The CdII atom is six-coordinated in an octahedral configuration by one O and two N atoms of one Schiff base ligand and by the terminal N atom of a bridging thiocyanate ligand, defining the basal plane, and by the terminal S atom of another bridging thiocyanate ligand and by the O atom of a coordinated methanol molecule, occupying the axial positions. The molecules are linked through intermolecular O-HO hydrogen bonds, forming chains running along the b axis.

Cadmium↗
PubMed1996

Immunoblot and ultrastructural analysis of antigens extracted from Dichelobacter nodosus with potassium thiocyanate.

The antigens extracted from Dichelobacter nodosus with potassium thiocyanate were analyzed by western blotting with sera from footrot-free sheep and from sheep infected with D. nodosus to identify components specific for infection. Several components with molecular mass < 33 kD were associated with infection, particularly bands of 32.5 kD, 30.5 kD, and 28 kD. Components with molecular mass > 56 kD may be responsible for false-positive reactions observed when sera of footrot-free sheep react with the potassium thiocyanate extract in solid phase enzyme-linked immunosorbent assays (ELISAs). Bands of 62.5 kD, 56 kD, 40 kD, and 19 kD were recognized for most sheep regardless of their disease status or ELISA reactivity and therefore do not appear to be detected by the ELISA. No components of the potassium thiocyanate extract were completely specific for infection. Antigens in the extract were identified primarily on the cell envelope by immunogold electron microscopy. Labeling was concentrated in the periplasm, with minor labeling of the cell surface. The extract consisted of tangled strands of particles with electron-dense cores, and few vesicular structures were observed.

Animals↗
PubMed1995

The effects of thiocyanate on the intracellular ion concentrations of branchial epithelial cells of brown trout

Exposure of brown trout (Salmo trutta) in fresh water to 0.15 mmol l-1 external thiocyanate for 1 h resulted in a significant decrease in chlorine concentration in the branchial mitochondria-rich (MR) cells from 37 mmol l-1 to 22 mmol l-1. The intracellular sodium concentration in these cells decreased by a similar amount, whilst the intracellular phosphorus concentration increased significantly. In contrast to the MR cells, 0.15 mmol l-1 external thiocyanate had no effect on the intracellular ion concentrations in the pavement epithelial cells. Thiocyanate is known to inhibit chloride uptake in a number of freshwater animals and therefore these data suggest that it is only the MR cells that are involved in the uptake of Cl- in brown trout.

Journal Article↗
PubMed1996

Blood antioxidant status and urine sulfate and thiocyanate levels in smokers.

Erythrocyte and plasma antioxidant enzyme activities and antioxidants as well as concentrations of total sulfate and thiocyanate were estimated in a group of healthy subjects and three groups of smokers (cigarette smokers, mixed tobacco smokers, and miscellaneous tobacco smokers). Plasma vitamin E, uric acid, ascorbic acid, ceruloplasmin, and urinary total sulfate concentrations were decreased, whereas dehydroascorbate and urinary thiocyanate concentrations were elevated in the three groups of smokers in comparison to the corresponding levels of the control subjects. On the other hand, erythrocyte superoxide dismutase and catalase as well as plasma superoxide dismutase activities were elevated in subjects of the three groups of smokers compared with the corresponding activity in subjects of the control group. Plasma catalase activity is statistically unaffected by smoking, but blood glutathione peroxidase activities were decreased in the three groups of smokers in comparison with the corresponding levels of the control group. There were also statistically meaningful differences between mean values of the antioxidant concentrations and the activities of the antioxidant enzymes in most of the smokers groups.

Adult↗
PubMed2003

Thiocyanate overload and thyroid disease.

Thiocyanate [SCN-] is a complex anion which is a potent inhibitor of iodide transport. It is the detoxification product of cyanide and can easily be measured in body fluids. Consumption of naturally occurring goitrogens, certain environmental toxins and cigarette smoke can significantly increase SCN- concentrations to levels potentially capable of affecting the thyroid gland. Goiter endemics were reported to develop when the critical urinary iodine/ SCN- ratio decreases below 3 microg iodine per mg SCN-. Iodine supplementation completely reverses the goitrogenic influence of SCN-. SCN- is also generated from cigarette smoking as a detoxifying product of cyanide. During the past two decades many reports dealt with the possible effects of cigarette smoking on thyroid hormone synthesis, thyroid gland size and thyroid autoimmunity including infiltrative ophtalmopathy of Graves' disease. In this mini-review, issues regarding thiocyanate overload and thyroid disease will be summarized.

Humans↗
PubMed1997

Inactivation of yeast and filamentous fungi by the lactoperoxidase-hydrogen peroxide-thiocyanate-system.

The antifungal activity of the lactoperoxidase (LPO) system with glucose oxidase (GOD) as source of hydrogen peroxide was determined in salt solution and in apple juice. The test organisms Rhodutorula rubra and Saccharomyces cerevisiae were cultivated aerobically in apple juice, Mucor rouxii was grown on wort agar adjusted to pH 4.5. Aspergillus niger and Byssochlamys fulva were kept on malt extract agar. Spores of the filamentous fungi were harvested by suspension in salt solution supplemented with Tween 80 and checked microscopically. The antifungal activity of the combined enzyme system was tested with initial counts of approx. 10(5) cfu.ml-1 (yeast cells or spores) suspended in salt solution supplemented with 25 mg.l-1 thiocyanate and 20 g.l-1 glucose or in apple juice supplemented with the same amount of thiocyanate. The tests were performed with 25 ml of the medium in 100 ml Erlenmeyer flasks shaken at 28 degrees C under aerobic conditions. Inactivation was achieved for all test organisms in both media. The yeast strains were found to be least stable while B. fulva was most resistant. A combination of 5 U.ml-1 LPO with 0.5 to 1 U.ml-1 GOD was sufficient for complete inactivation of this mold in salt solution within 2 h. The enzyme system also showed antifungal activity in apple juice at acid pH (3.2), although its effectiveness was reduced. In this medium, B. fulva was inactivated by 20 U.ml-1 LPD and 1 U.ml-1 GOD within 4 h. R. rubra and S. cerevisfiae were unable to survive in apple juice at 5 U.ml-1 LPO combined with 1 U.ml-1 GOD. For inhibition by GOD alone, higher amounts of this enzyme were needed and even then only M. rouxii and R. rubra have been affected within the concentration range tested (maximum 3 U.ml-1).

Antifungal Agents↗
PubMed1993

Use of thiocyanate ion as a mediator ligand in connecting acidic and alkaline forms of ferric myoglobin via paramagnetic 1H-NMR saturation transfer.

Paramagnetic 1H-NMR saturation transfer experiments have been used successfully to connect acidic and alkaline forms of equine ferric myoglobin through met-thiocyanate form as a mediator. The saturation transfer connectivities have provided the first assignments of the heme methyl proton resonances of equine met-hydroxyl myoglobin. Without mediator ligand, the acid-alkaline transition in this myoglobin is not accessible to the present technique due to the rapid exchange process between the two forms. Analysis of the intrinsic spin-lattice relaxation time and saturation transfer factor provided the life-time of met-thiocyanate and equine met-hydroxyl myoglobins under the experimental conditions used.

Acids↗
PubMed1999

Magnesium modulates contractile responses of rat aorta to thiocyanate: A possible relationship to smoking-induced atherosclerosis.

Thiocyanate anions (SCN-) as the end products of tobacco smoke and found in the blood of cigarette smokers have been implicated in atherogenesis and heart diseases. Magnesium deficiency has also been implicated in the etiology of atherogenesis. The contractile responses of rat aorta to SCN- and the modulation of extracellular magnesium ions ([Mg2+]o) on the effect of SCN- were, therefore, studied in isolated rat aortic rings. SCN- exposure at a range of concentrations (from 10(-5) to 5 x 10(-2) M) induces contractile responses of isolated rat aortic rings with and without endothelium in a concentration-dependent manner. Significant differences in responsiveness to SCN- were found in rat aortic ring segments with and without endothelial cells. Preincubation of these vessels with low [Mg2+]o markedly shifted the contractile concentration-effect curves to the left, and the contractile effects of SCN- in rat aortic rings were potentiated. In contrast to lowering [Mg2+]o, increasing [Mg2+]o to 2.4 mM was found to dramatically attenuate the contractile responses to SCN-. In the absence of extracellular Ca2+ ([Ca2+]o), SCN--induced contractions were, however, almost abolished after exposure to Mg2+-free medium. In order to investigate the mechanisms of [Mg2+]o modulation of SCN--induced contractile response of rat aorta, changes in intracellular Ca2+ ([Ca2+]i) were measured in cultured primary smooth muscle cells isolated from rat aorta. The resting level of [Ca2+]i in the rat aortic smooth muscle cells was 80.6 +/- 6.6 nM. Exposure of these cells to SCN- (5 x 10(-5) to 5 x 10(-3) M) produced rises in [Ca2+]i in a concentration-dependent manner. Preincubation of these cells with low [Mg2+]o (0 or 0.3 mM, the lowest physiological range) for 24 h significantly potentiated increments in [Ca2+]i induced by SCN-. These rises in [Ca2+]i induced by SCN- were completely inhibited by pretreating the cells with 2.4 mM [Mg2+]o for 24 h. These results support a hypothesis whereby cigarette smoking or exposure to smoking can induce cardiovascular diseases, at least partly, probably by causing spasm and thickening of arterial blood vessels as a consequence of large rises in [Ca2+]i in vascular smooth muscle cells. The chronic presence of or exposure to both thiocyanate and low Mg2+ in the blood of smokers can result in rapid flux of Ca2+ into vascular smooth muscle cells, thus accelerating or initiating atherosclerotic processes in smokers.

Animals↗
PubMed1988

Evaluation of nicotine, cotinine, thiocyanate, carboxyhemoglobin, and expired carbon monoxide as biochemical tobacco smoke uptake parameters.

In a cross-sectional study on 236 individuals in Japan (174 males, 62 females; 149 smokers, 87 non-smokers) plasma nicotine (pnic), cotinine (pcot) and thiocyanate (pSCN), urinary creatinine ratios of nicotine (unic), cotinine (ucot) and thiocyanate (uSCN) as well as carboxyhemoglobin (COHb) and expired carbon monoxide (COex) were determined. All tobacco smoke uptake parameters (TSUP) were significantly elevated in smokers as compared to nonsmokers. The discriminant power (smokers vs nonsmokers) rank in the following order: ucot approximately pcot approximately unic greater than pSCN approximately COHb approximately pnic greater than COex approximately uSCN. All parameters except for pnic are significantly correlated with the self-reported number of cigarettes smoked per day. The reason for the poor correlation of pnic with daily cigarette consumption is the short half-life of pnic coupled with the arbitrary time of blood drawing in relation to the last time of smoking.

Adult↗
PubMed1981

[The problem of nitrate and nitrite in human food. II. The occurrence of nitrate, nitrite, and thiocyanate in human saliva (author's transl)].

When the alimentary nitrate intake is in the range of 50 mg NO3- the nitrate values in saliva of adults and children follow a Gaussian normal distribution. With high and very high nitrate intakes the individual fluctuations of nitrate in saliva are distributed randomly in a wide range with a factor of 1:4. The nitrite values in saliva fluctuate even more, so that a proper judgment should be made only in individual cases. The average content of thiocyanate in saliva of adults was found to be 134 ppm SCN-, the saliva of children contained 50 ppm SCN-. The estimated molecular ratio of thiocyanate to nitrite in saliva of adults and children may fluctuate between 8:1 and 1:1 depending on the nitrate content of food.

Adult↗
PubMed1978

Effect of sodium nitroprusside alone and in combination with sodium thiosulfate on the acid-base balance, and on thiocyanate and iron plasma levels in the rabbit.

An infusion of 7.5 mg/kg.h sodium nitroprusside (SNP) produced a fatal cyanide intoxication in conscious rabbits (n=6) after 60.8 +/- 6.7 min (chi +/- S.E.). When, however, the cyanide antidote sodium thiosulfate was infused simultaneously at a rate of 31.25 or 62.5 mg/kg.h, i.e. a molar SNP/thiosulfate ratio of 1:5 or 1:10 respectively, this high dose of SNP was well tolerated. In both concentrations, thiosulfate abolished the development of the severe metabolic acidosis that results from the infusion of toxic doses of SNP alone. In the presence of thiosulfate, the plasma level of thiocyanate rose linearly with the infusion time indicating a rapid detoxification of cyanide released in vivo from SNP, whereas at the end of the infusion of SNP alone no increase in plasma thiocyanate could be measured. No clear advantage of the higher thiosulfate dosage over the lower one could be established. The iron plasma level only rose during the first hour of SNP plus thiosulfate infusions reaching the iron binding capacity of plasma, and then remained stable throughout the experiment. This indicates that the iron plasma level is an unsuitable parameter for the control of SNP therapy. We suggest the simultaneous administration of SNP and thiosulfate at a molar ratio of 1:5 to make SNP a safer drug.

Acid-Base Equilibrium↗
PubMed1989

Nitroprusside in children after cardiopulmonary bypass: a study of thiocyanate toxicity.

Thiocyanate levels, an indicator of nitroprusside toxicity, were studied in 22 children after repair of structural heart disease during cardiopulmonary bypass. At the total dose (2.6 +/- 2.3 mg/kg) and time (34.4 +/- 19 h) ranges of this study, no evidence of toxicity was detected, despite this total dose exceeding recommended maximum in some patients. Nitroprusside infusion, as described, in children with normal hepatic and renal function is safe and may not warrant routine assessment of thiocyanate levels.

Aspartate Aminotransferases↗
PubMed1996

Cell-free extract(s) of Pseudomonas putida catalyzes the conversion of cyanides, cyanates, thiocyanates, formamide, and cyanide-containing mine waters into ammonia.

Our isolate, Pseudomonas putida, is known to be capable of utilizing cyanides as the sole source of carbon (C) and nitrogen (N) both in the form of free cells and cells immobilized in calcium alginate. In the present study, the cell-free extract(s) were prepared from the cells of P. putida grown in the presence of sodium cyanide. The ability of enzyme(s) to convert cyanides, cyanates, thiocyanates, formamide and cyanide-containing mine waters into ammonia (NH3) was studied at pH 7.5 and pH 9.5. The kinetic analysis of cyanide and formamide conversion into NH3 at pH 7.5 and pH 9.5 by the cell-free extract(s) of P. putida was also studied. The Km and Vmax values for cyanide/formamide were found to be 4.3/8 mM and 142/227 mumol NH3 released mg protein-1 min-1 respectively at pH 7.5 and 5/16.67 mM and 181/434 mumol NH3 released mg protein-1 h-1 respectively at pH 9.5. The study thus concludes that the cell-free extract(s) of P. putida is able to metabolize not only cyanides, cyanates, thiocyanates, and formamide but also cyanide-containing mine waters to NH3.

Ammonia↗
PubMed2006

Histologic evaluation of effect of thiocyanate topical application on hamster cheek pouch.

The present study was conducted to investigate the effect of topical thiocyanate (SCN(-)) application on hamster cheek pouch mucosa. Sixty-six hamsters were divided into two groups. The test substance containing potassium thiocyanate was applied on the hamsters' cheek pouches at 55 mg/kg dosages. Cheek pouches were grossly examined after 12 weeks. Histometric evaluation included height measurements from the epithelium without stratum corneum, stratum corneum, and full epithelium. Clear cells frequency was compared between groups. Results were analyzed using Student's t test. The experimental group showed a lower height of the stratum corneum (p=0.035) and higher frequency of clear cells (p<0.001). There was no height difference for the epithelium without stratum corneum (p=0.677) and full epithelium (p=0.904) between groups. SCN(-) promotes no gross alterations on hamsters' cheek pouch and does not induce dysplastic features at the epithelium or inflammation at the connective tissue. The ion promotes histologic alterations on mucosa that need to be investigated in further studies.

Administration, Topical↗