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Determination of stability constants of mercury(II) by garlic organosulfur ligands with differential pulse voltammetry

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Abstract

In this work, interactions of mercury with di allyl disulfide (DADS), dimethyl disulfide (DMDS), and diallyl sulfide (DAS) were studied by differential pulse voltammetry. A thorough investigation was carried out on the complexation of mercury(II) by the garlic organosulfur ligands DADS, DMDS, and DAS at different steps. The optimal measurement conditions were conducted to determine the corresponding stability constants. The determination of stability constants of the labile mercury(II) with DADS, DMDS, and DAS complexes were based on the DE Ford-Hume methodology (equation) that calculated from the dependence of the shift of mercury(II) peak potential upon addition of the DADS, DMDA and DAS ligands separately. The results of this study provide evidence of the formation of 1:1 complexes between mercury(II) and DADS, DMDS, and DAS with the computed logβ1 values of the formation constants: (DADS): log β1 = 5.32 ± 0.46, (DMDS): log β1 = 5.40 ± 0.38, (DAS): log β1 = 4.61 ± 0.5 respectively.

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References

  1. Ahmadi F, Vahedpour T, Alizadeh AA (2018) The evaluation of Cr-curcumin-DNA complexation by experimental and theoretical approaches. Nucleos Nucleot Nucl Acids 37:35–52

    Article  CAS  Google Scholar 

  2. Ali S, Hussain S, Khan R, Mumtaz S, Ashraf N, Andleeb S, Shakir HA, Tahir HM, Khan MKA, Ulhaq M (2019) Renal toxicity of heavy metals (cadmium and mercury) and their amelioration with ascorbic acid in rabbits. Environ Sci Pollu Res 26:3909–3920

    Article  CAS  Google Scholar 

  3. Arreola R, Quintero-Fabián S, López-Roa RI, Flores-Gutiérrez EO, Reyes-Grajeda JP, Carrera-Quintanar L, Ortuño-Sahagún D (2015) Immunomodulation and anti-inflammatory effects of garlic compounds. J Immunol Res 2015:401630

    PubMed  PubMed Central  Google Scholar 

  4. Bard AJ, Faulkner LR (2002) Fundamentals and applications. Springer, New York

    Google Scholar 

  5. Bonfil Y, Brand M, Kirowa-Eisner E (2000) Determination of mercury and copper in waste water by anodic-stripping voltammetry at the gold electrode. Rev Anal Chem 19:201–216

    Article  CAS  Google Scholar 

  6. Bonfil Y, Brand M, Kirowa-Eisner E (2000) Trace determination of mercury by anodic stripping voltammetry at the rotating gold electrode. Anal Chim Acta 424:65–76

    Article  CAS  Google Scholar 

  7. Boorman PM, Merrit CL, Nandana WS, Richardson JF (1986) Synthetic, structural, and spectroscopic studies of the ligating properties of organic disulphides: x-ray structures of mercury (II) chloride–dimethyl disulphide (1/1) and triethylammonium trichloromercurate. J Chem Soc Dalton Trans 6:1251–1255

    Article  Google Scholar 

  8. Bose-O’Reilly S, Schierl R, Nowak D, Siebert U, William JF, Owi FT, Ir YI (2016) A preliminary study on health effects in villagers exposed to mercury in a small-scale artisanal gold mining area in Indonesia. Environ Res 149:274–281

    Article  PubMed  CAS  Google Scholar 

  9. Bradley JM, Organ CL, Lefer DJ (2016) Garlic-derived organic polysulfides and myocardial protection. J Nut 146:403S-409S

    Article  CAS  Google Scholar 

  10. Brown SD, BearJr RS Jr (1993) Chemometric techniques in electrochemistry: a critical review. Critical Rev Anal Chem 24:99–131

    Article  CAS  Google Scholar 

  11. Carnes ME, Lindquist NR, Zakharov LN, Johnson DW (2012) Counterion and steric effects in self-assembled HgX2–thioether coordination polymers. Crystal Growth Des 12:1579–1585

    Article  CAS  Google Scholar 

  12. Chan MC, Bautista E, Alvarado-Cruz I, Quintanilla-Vega B, Segovia J (2017) Inorganic mercury prevents the differentiation of SH-SY5Y cells: amyloid precursor protein, microtubule associated proteins and ROS as potential targets. J Trace Elements Med Biol 41:119–128

    Article  CAS  Google Scholar 

  13. Chekmeneva E, Díaz-Cruz JM, Ariño C, Esteban M (2009) Study of the Hg2+ binding with chelation therapy agents by differential pulse voltammetry on rotating Au-disk electrode and electrospray ionization mass-spectrometry. Anal Chim Acta 653:77–85

    Article  CAS  PubMed  Google Scholar 

  14. Chekmeneva E, Díaz-Cruz JM, Ariño C, Esteban M (2009) Binding of Hg2+ with phytochelatins: study by differential pulse voltammetry on rotating Au-disk electrode, electrospray ionization mass-spectrometry, and isothermal titration calorimetry. Environ Sci Technol 43:7010–7015

    Article  CAS  PubMed  Google Scholar 

  15. Chi MS (1982) Effects of garlic products on lipid metabolism in cholesterol-fed rats. Procee Soci Experi Biol Med 171:174–178

    Article  CAS  Google Scholar 

  16. Clarkson TW, Magos L, Myers GJ (2003) The toxicology of mercury—current exposures and clinical manifestations. New England J Med 349:1731–1737

    Article  CAS  Google Scholar 

  17. da Silva JCE, Machado AA (1995) Evolving factor analysis of synchronous fluorescence spectra of humic substances in the presence of Cu (II). Chemo Intelli Lab Sys 27:115–128

    Article  Google Scholar 

  18. Dai X, Compton RG (2006) Direct electrodeposition of gold nanoparticles onto indium tin oxide film coated glass: application to the detection of arsenic (III). Anal Sci 22:567–570

    Article  CAS  PubMed  Google Scholar 

  19. Diaz-Cruz M, Diaz-Cruz J, Mendieta J, Tauler R, Esteban M (2000) Soft-and hard-modeling approaches for the determination of stability constants of metal–peptide systems by voltammetry. Anal Biochem 279:189–201

    Article  CAS  PubMed  Google Scholar 

  20. El-Saeed GS, Abdel Maksoud SA, Bassyouni HT, Raafat J, Agybi MH, Wahby AA, Aly HM (2016) Mercury toxicity and DNA damage in patients with down syndrome. Medical Res J 15:22–26

    Article  Google Scholar 

  21. Esdaile LJ, Chalker JM (2018) The mercury problem in artisanal and small-scale gold mining. Chem Europ J 24:6905–6916

    Article  CAS  Google Scholar 

  22. Esteban M, Arino C, Díaz-Cruz J (2006) Chemometrics for the analysis of voltammetric data. TrAC Trends Anal Chem 25:86–92

    Article  CAS  Google Scholar 

  23. Gasper JD, Aiken GR, Ryan JN (2007) A critical review of three methods used for the measurement of mercury (Hg2+)-dissolved organic matter stability constants. Appl Geochem 22:1583–1597

    Article  CAS  Google Scholar 

  24. Ghizoni H, de Souza V, Straliotto MR, de Bem AF, Farina M, Hort MA (2017) Superoxide anion generation and oxidative stress in methylmercury-induced endothelial toxicity in vitro. Toxicol In Vitro 38:19–26

    Article  CAS  PubMed  Google Scholar 

  25. Giacomino A, Abollino O, Malandrino M, Mentasti E (2008) Parameters affecting the determination of mercury by anodic stripping voltammetry using a gold electrode. Talanta 75:266–273

    CAS  PubMed  Google Scholar 

  26. Gonçalves A, Pilla V, Oliveira E, Santos S, Capelo J, Dos Santos A, Lodeiro C (2016) The interaction of Hg2+ and trivalent ions with two new fluorescein bio-inspired dual colorimetric/fluorimetric probes. Dalton Trans 45:9513–9522

    Article  PubMed  CAS  Google Scholar 

  27. Gusmão R, Ariño C, Díaz-Cruz JM, Esteban M (2010) Electrochemical survey of the chain length influence in phytochelatins competitive binding by cadmium. Anal Bioche 406:61–69

    Article  CAS  Google Scholar 

  28. Heeg MJ, Elder R, Deutsch E (1979) Ligating ability of the coordinated thiolato sulfur atom. Interactions between soft-metal centers and the thiolatocobalt (III) complexes. Inorg Chem 18:2036–2039

    Article  CAS  Google Scholar 

  29. Hogan DE (2016) Biosurfactant (monorhamnolipid) complexation of metals and applications for aqueous metalliferous waste remediation. University of Arizona, Arizona

    Google Scholar 

  30. Horvat M, Hintelmann H (2007) Mercury analysis. Springer, New York

    Book  Google Scholar 

  31. Inkpen MS, Liu ZF, Li H, Campos LM, Neaton JB, Venkataraman L (2019) Non-chemisorbed gold–sulfur binding prevails in self-assembled monolayers. Nat Chem 11:351

    Article  CAS  PubMed  Google Scholar 

  32. Jalalvand AR, Goicoechea HC (2017) Applications of electrochemical data analysis by multivariate curve resolution-alternating least squares. TrAC Trends Anal Chem 88:134–166

    Article  CAS  Google Scholar 

  33. Ju H, Leech D (2000) Electrochemical study of a metallothionein modified gold disk electrode and its action on Hg2+ cations. J Electroanal Chem 484:150–156

    Article  CAS  Google Scholar 

  34. Keller H, Massart D (1991) Evolving factor analysis. Chemo Intelli Lab Sys 12:209–224

    Article  Google Scholar 

  35. Liu J, Lu Y-F, Li W-K, Zhou Z-P, Li Y-Y, Yang X, Li C, Du Y-Z, Wei L-X (2016) Mercury sulfides are much less nephrotoxic than mercury chloride and methylmercury in mice. Toxicol Lett 262:153–160

    Article  CAS  PubMed  Google Scholar 

  36. Maeder M, Zilian A (1988) Evolving factor analysis, a new multivariate technique in chromatography. Chemo Intelli Lab Sys 3:205–213

    Article  CAS  Google Scholar 

  37. Mao A, Li H, Cai Z, Hu X (2015) Determination of mercury using a glassy carbon electrode modified with nano TiO2 and multi-walled carbon nanotubes composites dispersed in a novel cationic surfactant. J Electroanal Chem 751:23–29

    Article  CAS  Google Scholar 

  38. McAuliffe CA (2016) The chemistry of mercury. Springer, New York

    Google Scholar 

  39. Milner J (1999) Functional foods and health promotion. J Nut 129:1395S-1397S

    Article  CAS  Google Scholar 

  40. Milner JA (1996) Garlic: its anticarcinogenic and antitumorigenic properties. Nutr Rev 54:S82-86

    Article  CAS  PubMed  Google Scholar 

  41. Miretzky P, Cirelli AF (2009) Hg (II) removal from water by chitosan and chitosan derivatives: a review. J Hazard Mater 167:10–23

    Article  CAS  PubMed  Google Scholar 

  42. Mohapatra S, Sahu S, Sinha N, Bhutia SK (2015) Synthesis of a carbon-dot-based photoluminescent probe for selective and ultrasensitive detection of Hg2+ in water and living cells. Analyst 140:1221–1228

    Article  CAS  PubMed  Google Scholar 

  43. Nesci S, Trombetti F, Pirini M, Ventrella V, Pagliarani A (2016) Mercury and protein thiols: stimulation of mitochondrial F1Fo-ATPase and inhibition of respiration. Chem Biol Interactions 260:42–49

    Article  CAS  Google Scholar 

  44. Oehmen A, Vergel D, Fradinho J, Reis MA, Crespo JG, Velizarov S (2014) Mercury removal from water streams through the ion exchange membrane bioreactor concept. J Hazard materials 264:65–70

    Article  CAS  Google Scholar 

  45. Officioso A, Tortora F, Manna C (2016) Nutritional aspects of food toxicology: mercury toxicity and protective effects of olive oil hydroxytyrosol. J Nutr Food Sci 6:2

    Google Scholar 

  46. Omer KH, Seliman AA, Al-Mohsin HA, Kawde AN, Altaf M, Wazeer MI, Ahmad S, Musa MM, Isab AA (2017) Study of the interaction of some potential anticancer gold (III) complexes with biologically important thiols using NMR, UV–vis, and electrochemistry. Inter J Chem Kinetics 49:387–397

    Article  CAS  Google Scholar 

  47. Pérez-Ràfols C, Serrano N, Díaz-Cruz JM, Ariño C, Esteban M (2017) A screen-printed voltammetric electronic tongue for the analysis of complex mixtures of metal ions. Sens Actuat Chem 250:393–401

    Article  CAS  Google Scholar 

  48. Romero I, Sánchez-Castelló G, Teixidor F, Whitaker CR, Rius J, Miravitlles C, Flor T, Escriche L, Casabó J (1996) Silver (I), mercury (II) and copper (I) complexes of acyclic and macrocyclic dithioether, metaxylyl based ligands. Polyhedron 15:2057–2065

    Article  CAS  Google Scholar 

  49. Rose P, Whiteman M, Moore PK, Zhu YZ (2005) Bioactive S-alk (en) yl cysteine sulfoxide metabolites in the genus Allium: the chemistry of potential therapeutic agents. Nat Product Rep 22:351–368

    Article  CAS  Google Scholar 

  50. Shao D, Wu S, Liang P, Kang Y, Fu W, Zhao K, Cao Z, Wong MH (2012) A human health risk assessment of mercury species in soil and food around compact fluorescent lamp factories in Zhejiang Province, PR China. J Hazard Mater 221:28–34

    Article  PubMed  CAS  Google Scholar 

  51. Steinberg S, Hodge V (2018) Copper complexation by dissolved organic matter in arid soils: a voltametric study. Environments 5:125

    Article  Google Scholar 

  52. Vigo L, Salin P, Oilunkaniemi R, Laitinen RS (2008) Catena-Poly [[chlorido (methyl phenyl sulfide-κS) mercury (II)]-μ-chlorido]. Acta Cryst 64:m809–m809

    CAS  Google Scholar 

  53. Yeh Y-Y, Liu L (2001) Cholesterol-lowering effect of garlic extracts and organosulfur compounds: human and animal studies. J Nut 131:989S-993S

    Article  CAS  Google Scholar 

  54. Zhao J, Gao Y, Li Y-F, Hu Y, Peng X, Dong Y, Li B, Chen C, Chai Z (2013) Selenium inhibits the phytotoxicity of mercury in garlic (Allium sativum). Environ Res 125:75–81

    Article  CAS  PubMed  Google Scholar 

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Acknowledgements

We are grateful to Imam Khomeini International University for supporting this work.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, JundiShapur University of Technology, Dezful, Iran

    Fatemeh Soleymani-Bonoti

  2. Department of Chemistry, Faculty of Science, Imam Khomeini International University, 34148-96818, Qazvin, Iran

    Rahman Bikas

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  1. Fatemeh Soleymani-Bonoti
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Correspondence to Fatemeh Soleymani-Bonoti.

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Soleymani-Bonoti, F., Bikas, R. Determination of stability constants of mercury(II) by garlic organosulfur ligands with differential pulse voltammetry. J Appl Electrochem 51, 1361–1370 (2021). https://doi.org/10.1007/s10800-021-01577-7

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