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Chelation in Metal Intoxication XLVI:Synthesis of Someα-Mercapto-β-Substituted Aryl Acrylic Acids and TheirIn vitro Cadmium Chelating Ability

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Biomedical and Environmental Sciences 2004年第1期17卷 27-32页

作者： MADHUMITA CHATTERJEE VINOD k.DWIVEDI kIRTI kHANDEkAR sushil k.tandon Chelation Therapy Division Industrial Toxicology Research CenterM.G.MargLucknow-226 001.IndiaChelation Therapy DivisionIndustrial Toxicology Research CenterM.G.MargLucknow-226 001.IndiaChelation Therapy DivisionIndustrial Toxicology Research CenterM.G.MargLucknow-226 001.IndiaChelation Therapy DivisionIndustrial Toxicology Research CenterM.G.MargLucknow-226 001.India

Objective To synthesize some new a-mercapto-β-substituted aryl acrylic acids, characterize them and investigate their in vitro cadmium chelating ability. Methods Six α-mercapto-β-substituted aryl acrylic acids were prepared by the alkaline hydrolysis of 5- (aryl methylene) rhodanines, obtained from the condensation of substituted aldehydes and rhodanine following the reported procedure. The new compounds were characterized by elemental analysis, infrared (IR) and nuclear magnetic resonance (NMR) spectroscopy. The liver and kidney from cadmium chloride pre-administered rats were homogenized and their nuclear mitochondrial fraction (NMF) and supernatant cytosol fraction (SCF) were separated. A measured volume of each fraction was dialyzed separately using 'dialysis sack' against buffered-kCl medium containing a compound in the final concentration of 1×10-3 mol/L for 3 h at 37℃. The whole content of 'sack' was subjected to cadmium estimation following digestion with cone. Nitric acid was detected using flame atomic absorption spectrometer. Results The in vitro screening showed that α-mercapto-β-(p-methoxyphenyl) acrylic acid (compound 2) andα-mercapto-β-(m-methoxy, p-hydroxyphenyl) acrylic acid (compound 4) were more effective than α-mercapto-β-thienyl acrylic acid (compound 1) and a-mercapto-β-(p-dimethylaminophenyl) acrylic acid (compound 3) in mobilizing cadmium as their dialyzable chelates. The presence of a methoxy group on the phenyl moiety (compounds 2 and 4) increases the metal chelating ability of mercapto acrylic acids. Conclusions Compounds 2 and 4 seem to have accessibility to the cellular system and capability of chelating-out the intracellularly bound cadmium.

关键词： Acrylic acid Cadmium In vitro chelation IR /NMR spectra Rat Synthesis

The Lead-Chelating Effects of Substituted Dithiocarbamates

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Biomedical and Environmental Sciences 1990年第3期3卷 299-305页

作者： sushil k.tandon NOORUS S.HASHMI DEVENDRA N.kACHRU Industrial Toxicology Research Centre Post Box 80 Lucknow-226001 India

The effectiveness of certain substituted dithiocarbamates in mobilizing lead from preexposed rats was *** animals received 10mg Pb/kg/day, *** 8 weeks and were treated thereafter with 400μmol/kg, *** morpholine dithiocarbamate, tetraammonium ethylenediamine diacetic acid dithiocarbamate (EDDTC), ammonium diethanolamine dithiocarbamate (ADDTC), sodium diethyldithiocarbamate.N-benzyl-D-glucamine dithiocarbamate (NBGDTC), or dimercaptosuccinic acid, daily for 5 *** the chelating agents were effective in lowering the hepatic and renal burden of ***, and NBGDTC were also able to lower the long bone Pb *** lowering of Pb burden had no relationship to restoration of Pb-induced hematopoietic *** relatively lower lipophilicity of substituted dithiocarbamates, owing to the presence of hydrophilic groups, seems to be advantageous in preventing passage of metal chelale into the *** of the substituted dithiocarbamates caused excessive excretion of urinary Cu and *** and EDDTC appear to be promising in the management of Pb poisoning. 1990 Academic ***.

关键词： The Lead-Chelating Effects of Substituted Dithiocarbamates DMSA

Chelation in Metal Intoxication XLIV: Efficacy of α-Mercapto β-(5-Substituted, 2-Furyl) Acrylic Acids in Mobilizing Intracellularly Bound Cadmium in Rat

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Biomedical and Environmental Sciences 2000年第3期13卷 205-212页

作者： sushil k. tandon\+1, SATGUR PRASAD, AND SURENDRA SINGH Industrial Toxicology Research Centre, Lucknow_226001, India Indust. Toxicology Research Centre Lucknow 226001 India Indust. Toxicology Research Centre M. G. Marg Lucknow-226001 India

The efficacy of α mercapto β (2_furyl) acrylic acid (MFA), α mercapto β (5_sodiumsulfonate, 2_furyl) acrylic acid (MSFA) and α mercapto β (5_acetoxymethyl, 2_furyl) acrylic acid (MAFA) to mobilize intracellularly bound cadmium in liver and kidney was investigated in rats pre_exposed to cadmium. MFA was effective in reducing cadmium levels of hepatic and renal supernatant cytosolic fraction (SCF) while MSFA and MAFA were effective in lowering cadmium levels of renal SCF and hepatic SCF respectively. All the chelating agents also enhanced the excretion of cadmium more in feces than in urine. However, substitution on the furan ring lowered cadmium mobilizing efficacy of the parent compound, MFA. The treatment with MFA did not affect the status of endogenous zinc and copper while the treatment with MSFA and MAFA enhanced their excretion. MSFA increased hepatic and renal zinc and renal copper while MAFA increased their copper levels.

关键词： Mercapto Substituted Chelation in Metal Intoxication XLIV Furyl Intracellularly Bound Cadmium in Rat Efficacy of Acrylic Acids in Mobilizing

Influence of Methionine Supplementation in Chelation of Lead in Rats1

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Biomedical and Environmental Sciences 1989年第3期2卷 265-270页

作者： DEVENDRAN.kACHRU SHASHIkHANDELWAL sushilk.tandon Industrial Toxicology Research Centre Post Box 80 Lucknow-226001 India

The influence of methionine supplementation on the efficacy of common antidotes to lead poisoning, calcium disodium ethylenediaminetetraacetate (CaNa_2EDTA) and D-penicillamine (DPA), was investigated in rats. The animals were given lead acetate (0.1% in drinking water) for 12 weeks and thereafter treated with CaNa_2EDTA, DPA (0.3mmol/kg, intraperitoneally), DL-methionine (1.34 mmol/kg, intragastrically), or the combination of a chelating agent and methionine for 3 days. While chelating agents enhanced the urinary excretion of Pb, methionine increased the fecal excretion of Pb significantly. Treatment with the combination of a chelating agent and methionine did not potentiate the effect of each antidote. However, methionine supplementation increased the efficacy of both chelating agents in reducing the hepatic and renal Pb burden but not the blood Pb level. The Pb-induced inhibition of blood δ-aminolevulinic acid dehydratase activity and the increase in urinary excretion of δ-aminolevulinic acid were reversed to a certain extent by CaNa_2EDTA, DPA, and methionine but the combination did not improve their individual performances. The beneficial effects of methionine may be attributed to its ability to increase the bioavailability of glutathione (GSH), useful in chelating Pb and counteracting the toxic effects, as evidenced by restoration of the Pb-induced decrease in hepatic GSH level by treatment with methionine. Methionine may be useful as a supportive therapy in chelation of Pb. (c)1989 Academic Press. Inc.

关键词： Influence of Methionine Supplementation in Chelation of Lead in Rats1 Pb ALAD GSH