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Characterization of interaction between amino acids and fulvic-like organic matter by fluorescence spectroscopy combining thermodynamic calculation

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Abstract

Dissolved organic matter (DOM), as a very fine colloidal suspension, could inevitably affect the transformation process of dissolved organic nitrogen (DON) in drinking water treatment. Tryptophan and tyrosine were used as representatives of DON to investigate the interactions between amino acids and fulvic-like components of fluorescent DOM using titration experiments. The fluorescence intensity decreased significantly with the increasing fulvic acid (FA) concentration, suggesting that FA could greatly quench the intrinsic fluorescence of amino acids such as tryptophan and tyrosine. The absolute spectrum peaks of amino acids (AA) were changed in the presence of FA, possibly being resulted from non-covalent interactions between amino acids and FA. The specific hydrogen bonding and van der Waals forces played dominant roles in the interactions according to the results of theoretical analysis and thermodynamic calculation. The distance between donor and acceptor was 1.25 and 1.14 nm for the FA–tyrosine and FA–tryptophan system, indicating the energy transfer from tyrosine or tryptophan to FA. The association constant (K) decreased with the increase of temperature and pH value, while the change of ionic strength had no obvious influence on K value.

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Abbreviations

DOM:

Dissolved organic matter

DON:

Dissolved organic nitrogen

FA:

Fulvic acids,

N-DBPs:

Nitrogenous disinfection by-products

THMs:

Trihalomethanes

FDOM:

Fluorescent dissolved organic matter

AA:

Amino acids

References

  • Bardhan M, Chowdhury J, Ganguly T (2011) Investigations on the interactions of aurintricarboxylic acid with bovine serum albumin: steady state/time resolved spectroscopic and docking studies. JPhotochemPhotobiol B 102:11–19

    Article  CAS  Google Scholar 

  • Dotson A, Westerhoff P, Krasner SW (2009) Nitrogen enriched dissolved organic matter (DOM) isolates and their affinity to form emerging disinfection by-products. Water Sci Technol 60:135–143

    Article  CAS  Google Scholar 

  • Fuhrman J (1990) Dissolved free amino acid cycling in an estuarine outflow plume. Mar Ecol Prog Ser 66:197–203

    Article  CAS  Google Scholar 

  • Helal AA, Imam DM, Khalifa SM, Aly HF (2006) Interaction of pesticides with humic compounds and their metal complexes. Radiochemistry 48(4):419–425

    Article  CAS  Google Scholar 

  • Her N, Amy G, Jarusutthirak C (2000) Seasonal variations of nanofiltration (NF) foulants: identification and control. Desalination 132:143–160

    Article  CAS  Google Scholar 

  • Hernandez D et al (2006) Detection of copper(II) and zinc(II) binding to humic acids from pig slurry and amended soils by fluorescence spectroscopy. Environ Pollut 143(2):212–220

    Article  CAS  Google Scholar 

  • Hernandez-Ruiz S et al (2012) Quantifying PPCP interaction with dissolved organic matter in aqueous solution: combined use of fluorescence quenching and tandem mass spectrometry. Water Res 46:943–954

    Article  CAS  Google Scholar 

  • Holdgate GA, Ward WH (2005) Measurements of binding thermodynamics in drug discovery. Drug DiscovToday 10:1543–1550

    CAS  Google Scholar 

  • Hu YJ, Liu Y, Xiao XH (2009) Investigation of the interaction between human serum albumin. Biomacromolecules 10:517–521

    Article  CAS  Google Scholar 

  • Hur J, Williams MA, Schlautman MA (2006) Evaluating spectroscopic and chromatographic techniques to resolve dissolved organic matter via end member mixing analysis. Chemosphere 63(3):387–402

    Article  CAS  Google Scholar 

  • Kandagal PB, Seetharamappa J, Ashoka S, Shaikh SM, Manjunatha DH (2006) Study of the interaction between doxepin hydrochloride and bovine serum albumin by spectroscopic techniques. Int J Biol Macromol 39:234–239

    Article  CAS  Google Scholar 

  • Kandagal PB, Kalanur SS, Manjunatha DH, Seetharamappa J (2008) Mechanism of interaction between human serum albumin and N-alkyl phenothiazines studied using spectroscopic methods. J Pharm Biomed Anal 47:260–267

    Article  CAS  Google Scholar 

  • Keil RG, Kirchman DL (1991) Dissolved combined amino-acids in marine waters as determined by a vapor-phase hydrolysis method. Mar Chem 33:243–259

    Article  CAS  Google Scholar 

  • Lee W, Kang S, Shin H (2003) Sludge characteristics and their contribution to microfiltration in submerged membrane bioreactors. J Membr Sci 216:217–227

    Article  CAS  Google Scholar 

  • Lee W, Westerhoff P, Croue J (2007) Dissolved organic nitrogen as a precursor for chloroform, dichloroac etonitrile, N-nitrosodimethylamine, and trichloronitromethane. Environ Sci Technol 41:5485–5490

    Article  CAS  Google Scholar 

  • Leenheer JA (2004) Comprehensive assessment of precursors, diagenesis, and reactivity to water treatment of dissolved and colloidal organic matter. Water Sci Technol:Water Supply 4:1–9

    CAS  Google Scholar 

  • Lin H, Lan J, Guan M, Sheng F, Zhang H (2009) Spectroscopic investigation of interaction between mangiferin and bovine serum albumin. Spectrochim. Acta A Mol. Biomol. Spectrosc 73:936–941

    Article  Google Scholar 

  • Lu XQ, Jaffe R (2001) Interaction between Hg(II) and natural dissolved organic matter: a fluorescence spectroscopy based study. Water Res 35(7):1793–1803

    Article  CAS  Google Scholar 

  • Matei I, Hillebrand M (2010) Interaction of kaempferol with human serum albumin: a fluorescence and circular dichroism study. J Pharm Biomed Anal 51:768–773

    Article  CAS  Google Scholar 

  • Ogunsipe A, Nyokong T (2005) Photophysicochemical consequences of bovine serum albumin binding to non-transition metal phthalocyanine sulfonates. PhotochemPhotobiol Sci 4:510–516

    Article  CAS  Google Scholar 

  • Pehlivanoglu Mantas E, Sedlak DL (2008) Measurement of dissolved organic nitrogen forms in wastewater effluents: concentrations, size distribution and NDMA formation potential. Water Res 42:3890–3898

    Article  CAS  Google Scholar 

  • Peuravuori J, Pihlaja K (2004) Preliminary study of lake dissolved organic matter in light of nanoscale supramolecular assembly. Environ. Sci. Technol 38(22):5958–5967

    Article  CAS  Google Scholar 

  • Piccolo A (2001) The supramolecular structure of humic substances. Soil Sc 166(11):810–832

    Article  CAS  Google Scholar 

  • Piccolo A (2012) The nature of soil organic matter and innovative soil managements to fight global changes and maintain agricultural productivity. In: Piccolo A (ed) Carbon sequestration in agricultural soils. Springer Verlag, Heidelberg, pp 1–20

    Chapter  Google Scholar 

  • Plaza C, D’Orazio V, Senesi N (2005a) Copper(II) complexation of humic acids from the first generation of EUROSOILS by total luminescence spectroscopy. Geoderma 125:177–186

    Article  CAS  Google Scholar 

  • Plaza C, Brunetti G, Senesi N, Polo A (2006a) Molecular and quantitative analysis of metal ion binding to humic acids from sewage sludge and sludge-amended soils by fluorescence spectroscopy. Environ Sci Technol 40:917–923

    Article  CAS  Google Scholar 

  • Plewa MJ, Wagner ED, Jazwierska P, Richardson SD, Chen PH, McKague AB (2004) Halonitromethane drinking water disinfection byproducts: chemical characterization and mammalian cell cytotoxicity and genotoxicity. Environ Sci Technol 38:62–68

    Article  CAS  Google Scholar 

  • Richardson SD, Plewa MJ, Wagner ED, Schoeny R, DeMarini DM (2007) Occurrence, genotoxicity, and carcinogenicity of regulated and emerging disinfection byproducts in drinking water: a review and roadmap for research. Mutat Res 636:178–242

    Article  CAS  Google Scholar 

  • Romera-Castillo C, Chen ML, Yamashita Y, Jaffe R (2014) Fluorescence characteristics of size-fractionated dissolved organic matter: implications for a molecular assembly based structure? Water Res 55:40–51

    Article  CAS  Google Scholar 

  • Seetharamappa J, Kamat BP (2004) Spectroscopic studies on the mode of interaction of an anticancer drug with bovine serum albumin. Chem Pharm Bull (Tokyo) 52:1053–1057

    Article  CAS  Google Scholar 

  • Stuart W, Krasner WA, Mitch WA et al (2013) Formation, precursors, control, and occurrence of nitrosamines in drinking water: a review. Water Res 46:4433–4450

    Google Scholar 

  • Tipping E (2002) Cation binding by humic substances. Cambridge University Press, New York

    Book  Google Scholar 

  • Wan HB, Zhang YJ (2014) Mechanisms of interaction between polycyclic aromatic hydrocarbons and dissolved organic matters. J Environ Sci Health Part A Tox Hazard SubstEnviron Eng 49(1):78–84

    Article  Google Scholar 

  • Wang N, Ye L, Zhao BQ, Yu JX (2008) Spectroscopic studies on the interaction of efonidipine with bovine serum albumin. Braz J Med Biol Res 41:589–595

    Article  CAS  Google Scholar 

  • Wang Z, Cao J et al (2015) Interactions between protein-like and humic-like components in dissolved organic matter revealed by fluorescence quenching. Water Res 68:404–413

    Article  Google Scholar 

  • Westerhoff P, Mash H (2002) Dissolved organic nitrogen in drinking water supplies: a review. J Water Supply Res Technol 51:415–448

    CAS  Google Scholar 

  • Yamashita Y, Tanoue E (2003b) Distribution and alteration of amino acids in bulk DOM along a transect from bay to oceanic waters. Mar Chem 82(3–4):145–160

    Article  CAS  Google Scholar 

  • Yan JH, Yi L et al (2005) Studies of interaction between colchicine and bovine serum albumin by fluorescence quenching method. J Mol Struct 750:174–178

    Article  Google Scholar 

  • Zhang Y, Qi Z, Zheng D, Li C, Liu Y (2009) Interactions of chromium (III) and chromium (VI) with bovine serum albumin studied by UV spectroscopy, circular dichroism, and fluorimetry. Biol Trace Elem Res 130:172–184

    Article  CAS  Google Scholar 

  • Zhang G, Zhao N, Hu X, Tian J (2010) Interaction of alpinetin with bovine serum albumin: probing of the mechanism and binding site by spectroscopic methods. Spectrochim Acta A Mol Biomol Spectrosc 76:410–417

    Article  Google Scholar 

Download references

Acknowledgements

Financial support was received from the National Natural Science Foundation of China (Project 51438006), the Major Science and Technology Program for Water Pollution Control and Treatment (2014ZX07405002), and the funds sponsored by the Qing Lan Project and A Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions.

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Correspondence to Tao Lin.

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Responsible editor: Philippe Garrigues

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Lin, T., Hou, B., Wang, J. et al. Characterization of interaction between amino acids and fulvic-like organic matter by fluorescence spectroscopy combining thermodynamic calculation. Environ Sci Pollut Res 24, 7226–7235 (2017). https://doi.org/10.1007/s11356-017-8444-4

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