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We analyzed the binding of paraquat (PQ) and diquat (DQ) herbicides to natural calf thymus DNA and a DNA G-quadruplex by spectrophotometric titrations, ethidium bromide exchange tests, viscometry, and melting experiments. The interaction with bovine serum albumin (BSA) protein was studied spectrofluorimetrically at different temperatures. The retention of the targets on positive, negative, and neutral micellar aggregates and liposomes was analyzed by ultrafiltration experiments. Despite some favorable features, PQ and DQ only externally bind natural DNA and do not interact with DNA oligonucleotides. Both herbicides bind bovine serum albumin (BSA). PQ binds BSA mainly according to an electrostatics-driven process. However, ultrafiltration data also show that some hydrophobic contribution participates in the features of these systems. The practical problems related to unfavorable spectroscopic signals and inner filter effects are also discussed. Overall, both herbicides show a low affinity for nucleic acids and weak penetration into liposomes; in addition, the equilibrium constants values found for BSA system suggest optimal conditions for transport in the body.<\/jats:p>","DOI":"10.3390\/ijerph18052412","type":"journal-article","created":{"date-parts":[[2021,3,2]],"date-time":"2021-03-02T04:42:46Z","timestamp":1614660166000},"page":"2412","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Spectroscopic Analysis of the Binding of Paraquat and Diquat Herbicides to Biosubstrates"],"prefix":"10.3390","volume":"18","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6063-3729","authenticated-orcid":false,"given":"Francesca","family":"Macii","sequence":"first","affiliation":[{"name":"Department of Chemistry and Industrial Chemistry, University of Pisa, 56124 Pisa, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rebecca","family":"Detti","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Industrial Chemistry, University of Pisa, 56124 Pisa, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Francesca Rita","family":"Bloise","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Industrial Chemistry, University of Pisa, 56124 Pisa, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0052-0105","authenticated-orcid":false,"given":"Stefania","family":"Giannarelli","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Industrial Chemistry, University of Pisa, 56124 Pisa, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8512-8422","authenticated-orcid":false,"given":"Tarita","family":"Biver","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Industrial Chemistry, University of Pisa, 56124 Pisa, Italy"},{"name":"Department of Pharmacy, University of Pisa, 56126 Pisa, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,3,2]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Eddleston, M. (2016). Bipyridyl Herbicides. Critical Care Toxicology, Springer International Publishing. [2nd ed.].","DOI":"10.1007\/978-3-319-20790-2_100-1"},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Lohitnavy, M., Chitsakhon, A., Jomprasert, K., Lohitnavy, O., and Reisfeld, B. (2017). Development of a physiologically based pharmacokinetic model of paraquat. Proc. Annu. Int. Conf. IEEE Eng. Med. Biol. Soc. EMBS, 2732\u20132735.","DOI":"10.1109\/EMBC.2017.8037422"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"184","DOI":"10.2478\/intox-2014-0026","article-title":"Diquat-induced cytotoxicity on Vero and HeLa cell lines: Effect of melatonin and dihydromelatonin","volume":"7","author":"Zeman","year":"2014","journal-title":"Interdiscip. Toxicol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"104481","DOI":"10.1016\/j.jece.2020.104481","article-title":"Heracleum persicum based biosorbent for the removal of paraquat and diquat from waters","volume":"8","author":"Mehmandost","year":"2020","journal-title":"J. Environ. Chem. Eng."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"26","DOI":"10.1016\/j.geoderma.2017.01.027","article-title":"Retention of quaternary ammonium herbicides by acid vineyard soils with different organic matter and Cu contents","volume":"293","author":"Paradelo","year":"2017","journal-title":"Geoderma"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1016\/j.foodchem.2017.06.086","article-title":"Experimental and theoretical determination of pesticide processing factors to model their behavior during virgin olive oil production","volume":"239","year":"2018","journal-title":"Food Chem."},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Ortiz, G.G., Pacheco-Mois\u00e9s, F.P., Mireles-Ram\u00edrez, M.A., Flores-Alvarado, L.J., Gonz\u00e1lez-Usigli, H., S\u00e1nchez-L\u00f3pez, A.L., S\u00e1nchez-Romero, L., Vel\u00e1zquez-Brizuela, I.E., Gonz\u00e1lez-Renovato, E.D., and Torres-S\u00e1nchez, E.D. (2016). Oxidative Stress and Parkinson\u2019s Disease: Effects on Environmental Toxicology. Free Radicals and Diseases, IntechOpen Limited.","DOI":"10.5772\/63794"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"191","DOI":"10.1016\/j.envres.2016.01.003","article-title":"Magnitude and characteristics of acute paraquat- and diquat-related illnesses in the US: 1998\u20132013","volume":"146","author":"Fortenberry","year":"2016","journal-title":"Environ. Res."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1155\/2020\/7359582","article-title":"Separation and determination of paraquat and diquat in human plasma and urine by magnetic dispersive solid phase extraction coupled with high-performance liquid chromatography","volume":"2020","author":"Sha","year":"2020","journal-title":"J. Anal. Methods Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"209","DOI":"10.1016\/j.chroma.2018.12.022","article-title":"Development of a high-throughput screening analysis for 288 drugs and poisons in human blood using Orbitrap technology with gas chromatography-high resolution accurate mass spectrometry","volume":"1587","author":"Pan","year":"2019","journal-title":"J. Chromatogr. A"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1459","DOI":"10.36740\/WLek202007127","article-title":"Dermal absorption of diquat and potential occupational risk","volume":"73","author":"Yastrub","year":"2020","journal-title":"Wiad. Lek."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"105446","DOI":"10.1016\/j.aquatox.2020.105446","article-title":"Morphometric and proteomic responses of early-life stage rainbow trout (Oncorhynchus mykiss) to the aquatic herbicide diquat dibromide","volume":"222","author":"McCuaig","year":"2020","journal-title":"Aquat. Toxicol."},{"key":"ref_13","first-page":"3","article-title":"Andrographolide, an antioxidant, counteracts paraquatinduced mutagenesis in mammalian cells","volume":"21","author":"Tajai","year":"2020","journal-title":"Asian Pac. J. Cancer Prev."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"245","DOI":"10.1016\/j.biopha.2017.08.073","article-title":"Paraquat exposure-induced Parkinson\u2019s disease-like symptoms and oxidative stress in Drosophila melanogaster: Neuroprotective effect of Bougainvillea glabra Choisy","volume":"95","author":"Soares","year":"2017","journal-title":"Biomed. Pharmacother."},{"key":"ref_15","first-page":"6656","article-title":"Serum metabolic changes in rats of acute paraquat poisoning treated by pirfenidone","volume":"10","author":"Zhou","year":"2017","journal-title":"Int. J. Clin. Exp. Med."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"344","DOI":"10.1039\/C8FO02091D","article-title":"Resveratrol improves intestinal barrier function, alleviates mitochondrial dysfunction and induces mitophagy in diquat challenged piglets","volume":"10","author":"Cao","year":"2019","journal-title":"Food Funct."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"12825","DOI":"10.1002\/chem.201701618","article-title":"Synthesis, optical properties, and DNA interaction of new diquats based on triazolopyridines and triazoloquinolines","volume":"23","author":"Guijarro","year":"2017","journal-title":"Chem.\u2014A Eur. J."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"239","DOI":"10.1016\/S1383-5718(99)00197-7","article-title":"Genotoxicity of paraquat: Micronuclei induced in bone marrow and peripheral blood are inhibited by melatonin","volume":"464","author":"Ortiz","year":"2000","journal-title":"Mutat. Res.\u2014Genet. Toxicol. Environ. Mutagen."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"612","DOI":"10.1002\/tox.21787","article-title":"Genotoxic effects of glyphosate or paraquat on earthworm coelomocytes","volume":"29","author":"Muangphra","year":"2014","journal-title":"Environ. Toxicol."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1226","DOI":"10.1093\/ndt\/gfn615","article-title":"The clinical features of acute kidney injury in patients with acute paraquat intoxication","volume":"24","author":"Kim","year":"2009","journal-title":"Nephrol. Dial. Transplant."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"552","DOI":"10.1080\/01480545.2018.1488857","article-title":"Determination of LCt50 of aerosolized paraquat and its pulmonary toxic implications in non-anesthetized rats","volume":"42","author":"Mandal","year":"2019","journal-title":"Drug. Chem. Toxicol."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1533","DOI":"10.1016\/0006-2952(90)90451-P","article-title":"An evaluation of the redox cycling potencies of paraquat and nitrofurantoin in microsomal and lung slice systems","volume":"40","author":"Adam","year":"1990","journal-title":"Biochem. Pharmacol."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"101606","DOI":"10.1016\/j.redox.2020.101606","article-title":"Mitochondria-targeted paraquat and metformin mediate ROS production to induce multiple pathways of retrograde signaling: A dose-dependent phenomenon","volume":"36","author":"Chowdhury","year":"2020","journal-title":"Redox Biol."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1364","DOI":"10.1002\/tox.23001","article-title":"Reactive oxygen species regulate miR-17-5p expression via DNA methylation in paraquat-induced nerve cell damage","volume":"35","author":"Zhan","year":"2020","journal-title":"Environ. Toxicol."},{"key":"ref_25","first-page":"1","article-title":"Cellular effects of diquat dibromide exposure: Interference with Wnt signaling and cytoskeletal development","volume":"3","author":"Jalil","year":"2019","journal-title":"Toxicol. Res. Appl."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1131","DOI":"10.1177\/0960327118765330","article-title":"Human and experimental toxicology of diquat poisoning: Toxicokinetics, mechanisms of toxicity, clinical features, and treatment","volume":"37","author":"Carvalho","year":"2018","journal-title":"Hum. Exp. Toxicol."},{"key":"ref_27","doi-asserted-by":"crossref","unstructured":"Babalola, O.O., Truter, J.C., and Van Wyk, J.H. (2020). Lethal and Teratogenic Impacts of imazapyr, diquat dibromide, and glufosinate ammonium herbicide formulations using frog embryo teratogenesis assay-xenopus (FETAX). Arch. Environ. Contam. Toxicol.","DOI":"10.1007\/s00244-020-00756-5"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1267","DOI":"10.1016\/0002-9343(81)90836-6","article-title":"Diquat intoxication: Report of two cases and review of the literature","volume":"70","author":"Vanholder","year":"1981","journal-title":"Am. J. Med."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"655","DOI":"10.1016\/j.arabjc.2015.03.009","article-title":"Characterization of a sensitive biosensor based on an unmodified DNA and gold nanoparticle composite and its application in diquat determination","volume":"11","author":"Niu","year":"2018","journal-title":"Arab. J. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","unstructured":"Stobiecka, M. (2013). Novel DNA-Biosensors for Studies of GMO, Pesticides and Herbicides. State of the Art in Biosensors\u2014Environmental and Medical Applications, IntechOpen Limited.","DOI":"10.5772\/52261"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"92","DOI":"10.1016\/j.pestbp.2017.04.011","article-title":"Solvent-dependent binding interactions of the organophosphate pesticide, chlorpyrifos (CPF), and its metabolite, 3,5,6-trichloro-2-pyridinol (TCPy), with Bovine Serum Albumin (BSA): A comparative fluorescence quenching analysis","volume":"139","author":"Dahiya","year":"2017","journal-title":"Pestic. Biochem. Physiol."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"53","DOI":"10.1016\/j.toxlet.2003.10.014","article-title":"Methyl parathion interaction with human and bovine serum albumin","volume":"147","author":"Silva","year":"2004","journal-title":"Toxicol. Lett."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"165","DOI":"10.1186\/s12951-020-00725-z","article-title":"Self-assembled bovine serum albumin nanoparticles as pesticide delivery vectors for controlling trunk-boring pests","volume":"18","author":"Su","year":"2020","journal-title":"J. Nanobiotechnol."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"14188","DOI":"10.1039\/C7NJ01645J","article-title":"Exploring the binding mechanism of paraquat to DNA by a combination of spectroscopic, cellular uptake, molecular docking and molecular dynamics simulation methods","volume":"41","author":"Jafari","year":"2017","journal-title":"New J. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1080\/13510002.1997.11747088","article-title":"Redox stress and hepatic DNA fragmentation induced by diquat in vivo are not accompanied by increased 8-hydroxydeoxyguanosine contents","volume":"3","author":"Gupta","year":"1997","journal-title":"Redox Rep."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"35","DOI":"10.1007\/s10311-011-0325-3","article-title":"Evidence for DNA-diquat interaction and cytotoxicity in in vitro rat cells","volume":"10","author":"Zhang","year":"2012","journal-title":"Environ. Chem. Lett."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1016\/j.pestbp.2006.05.003","article-title":"Human serum albumin interaction with paraquat studied using spectroscopic methods","volume":"87","author":"Zhang","year":"2007","journal-title":"Pestic. Biochem. Physiol."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"36","DOI":"10.1016\/j.jhazmat.2014.03.022","article-title":"Study on the bindings of dichlorprop and diquat dibromide herbicides to human serum albumin by spectroscopic methods","volume":"273","author":"Duman","year":"2014","journal-title":"J. Hazard. Mater."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"5390","DOI":"10.1021\/acs.jafc.7b01895","article-title":"Evaluation of the Interaction between Pesticides and a Cell Membrane Model by Surface Plasmon Resonance Spectroscopy Analysis","volume":"65","author":"Moriwaki","year":"2017","journal-title":"J. Agric. Food Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"503","DOI":"10.1016\/j.bpj.2018.12.018","article-title":"Complex Phase Behavior of GUVs Containing Different Sphingomyelins","volume":"116","author":"Balleza","year":"2019","journal-title":"Biophys. J."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"247","DOI":"10.1016\/j.jcis.2019.06.028","article-title":"Magainin-H2 effects on the permeabilization and mechanical properties of giant unilamellar vesicles","volume":"553","author":"Mescola","year":"2019","journal-title":"J. Colloid Interface Sci."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"13669","DOI":"10.1021\/acs.langmuir.7b01841","article-title":"Daptomycin-phosphatidylglycerol domains in lipid membranes","volume":"33","author":"Kreutzberger","year":"2017","journal-title":"Langmuir"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"117313","DOI":"10.1016\/j.saa.2019.117313","article-title":"Binding of model polycyclic aromatic hydrocarbons and carbamate-pesticides to DNA, BSA, micelles and liposomes","volume":"223","author":"Macii","year":"2019","journal-title":"Spectrochim. Acta\u2014Part A Mol. Biomol. Spectrosc."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1531","DOI":"10.1016\/j.jinorgbio.2004.06.005","article-title":"Intercalation of Zn(II) and Cu(II) complexes of the cyclic polyamine Neotrien into DNA: Equilibria and kinetics","volume":"98","author":"Biver","year":"2004","journal-title":"J. Inorg. Biochem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"645","DOI":"10.1021\/acs.organomet.9b00681","article-title":"Exploring the anticancer potential of diiron bis-cyclopentadienyl complexes with bridging hydrocarbyl ligands: Behavior in aqueous media and in vitro cytotoxicity","volume":"39","author":"Agonigi","year":"2020","journal-title":"Organometallics"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"303","DOI":"10.1016\/j.colsurfa.2014.08.008","article-title":"Effects of micelle nature and concentration on the acid dissociation constants of the metal extractor PADA","volume":"461","author":"Aydinoglu","year":"2014","journal-title":"Colloids Surfaces A Physicochem. Eng. Asp."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"20061","DOI":"10.1039\/C4CP02838D","article-title":"Mechanistic aspects of thioflavin-T self-aggregation and DNA binding: Evidence for dimer attack on DNA grooves","volume":"16","author":"Biancardi","year":"2014","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_48","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.E., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., and Nakatsuji, H. (2016). Gaussian 16. Gaussian Inc. Wallingford CT."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"3032","DOI":"10.1063\/1.474659","article-title":"A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to Isotropic and anisotropic dielectrics","volume":"107","author":"Mennucci","year":"1997","journal-title":"J. Chem. Phys."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"2999","DOI":"10.1021\/cr9904009","article-title":"Quantum mechanical continuum solvation models","volume":"105","author":"Tomasi","year":"2005","journal-title":"Chem. Rev."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"87","DOI":"10.1016\/0022-2836(67)90353-1","article-title":"A fluorescent complex between ethidium bromide and nucleic acids. Physical-Chemical characterization","volume":"27","author":"Lepecq","year":"1967","journal-title":"J. Mol. Biol."},{"key":"ref_52","doi-asserted-by":"crossref","unstructured":"Rocco, D., Batchelor, L.K., Agonigi, G., Braccini, S., Chiellini, F., Schoch, S., Biver, T., Funaioli, T., Zacchini, S., and Biancalana, L. (2019). Anticancer potential of diiron vinyliminium complexes. Chem.\u2014A Eur. J., 1\u201317.","DOI":"10.1002\/chem.201902885"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"673","DOI":"10.1107\/S0365110X53001939","article-title":"The structure of sodium thymonucleate fibres. I. The influence of water content","volume":"6","author":"Franklin","year":"1953","journal-title":"Acta Crystallogr."},{"key":"ref_54","doi-asserted-by":"crossref","unstructured":"Lakowicz, J.R. (2006). Principles of Fluorescence Spectroscopy, Springer International Publishing. [3rd ed.].","DOI":"10.1007\/978-0-387-46312-4"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"111305","DOI":"10.1016\/j.jinorgbio.2020.111305","article-title":"Spectrofluorimetric analysis of the binding of a target molecule to serum albumin: Tricky aspects and tips","volume":"216","author":"Macii","year":"2021","journal-title":"J. Inorg. Biochem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"107","DOI":"10.1016\/j.jpba.2009.03.015","article-title":"Fluorescence spectral resolution of tryptophan residues in bovine and human serum albumins","volume":"50","author":"Tayeh","year":"2009","journal-title":"J. Pharm. Biomed. Anal."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"1088","DOI":"10.2174\/1389203719666180521092615","article-title":"The enthalpy-entropy compensation phenomenon. limitations for the use of some basic thermodynamic equations","volume":"19","author":"Khrapunov","year":"2018","journal-title":"Curr. Protein Pept. Sci."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"1324","DOI":"10.1039\/C4MD00057A","article-title":"A fundamental view of enthalpy-entropy compensation","volume":"5","author":"Ryde","year":"2014","journal-title":"Medchemcomm"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"301","DOI":"10.1007\/s00249-016-1182-6","article-title":"Enthalpy\u2013entropy compensation: The role of solvation","volume":"46","author":"Dragan","year":"2017","journal-title":"Eur. Biophys. J."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"2368","DOI":"10.1002\/chem.200204481","article-title":"A new strategy for the design of water-soluble synthetic receptors: Specific recognition of DNA intercalators and diamines","volume":"9","author":"Kenji","year":"2003","journal-title":"Chem.\u2014A Eur. J."},{"key":"ref_61","first-page":"824","article-title":"The characterization of two specific drug binding sites on human serum albumin","volume":"11","author":"Sudlow","year":"1975","journal-title":"Mol. Pharmacol."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"1107","DOI":"10.1016\/0045-6535(83)90264-3","article-title":"The octanol-water partitioning of some hydrophobic and hydrophilic compounds","volume":"12","author":"Platford","year":"1983","journal-title":"Chemosphere"},{"key":"ref_63","unstructured":"Tomlin, C.D.S. (2003). The Pesticide Manual, Royal Society of Chemistry. [13th ed.]."},{"key":"ref_64","first-page":"327","article-title":"Chapter 33. Plasma protein binding of drugs","volume":"31","author":"Olson","year":"1996","journal-title":"Annu. Rep. Med. Chem."},{"key":"ref_65","first-page":"996","article-title":"Designing prodrugs based on special residues of human serum albumin","volume":"9","author":"Gou","year":"2016","journal-title":"Curr. Top. Med. Chem."},{"key":"ref_66","first-page":"5","article-title":"Bovine serum albumin interactions with metal complexes","volume":"87","author":"Bodoki","year":"2014","journal-title":"Clujul Med."}],"container-title":["International Journal of Environmental Research and Public Health"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-4601\/18\/5\/2412\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T05:31:15Z","timestamp":1760160675000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-4601\/18\/5\/2412"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,3,2]]},"references-count":66,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2021,3]]}},"alternative-id":["ijerph18052412"],"URL":"https:\/\/doi.org\/10.3390\/ijerph18052412","relation":{},"ISSN":["1660-4601"],"issn-type":[{"value":"1660-4601","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,3,2]]}}}