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dc.contributor.authorŚwiderski, Grzegorz-
dc.contributor.authorKalinowska, Monika-
dc.contributor.authorGołębiewska, Ewelina-
dc.contributor.authorŚwisłocka, Renata-
dc.contributor.authorLewandowski, Włodzimierz-
dc.contributor.authorKowalczyk, Natalia-
dc.contributor.authorNaumowicz, Monika-
dc.contributor.authorCudowski, Adam-
dc.contributor.authorPietryczuk, Anna-
dc.contributor.authorNalewajko-Sieliwoniuk, Edyta-
dc.contributor.authorWysocka, Izabela-
dc.contributor.authorArciszewska, Żaneta-
dc.contributor.authorGodlewska-Żyłkiewicz, Beata-
dc.date.accessioned2026-02-04T07:29:44Z-
dc.date.available2026-02-04T07:29:44Z-
dc.date.issued2023-
dc.identifier.citationMolecules Volume 28 Issue 18, 2023, 6506pl
dc.identifier.urihttp://hdl.handle.net/11320/19741-
dc.description.abstractIn this study, we investigated the structures of lanthanide (Eu(III), Dy(III), and Gd(III)) complexes with p-coumaric (p-CAH2) and caffeic (CFAH3) acids using the FTIRKBr, FTIRATR, and Raman spectroscopic methods. The compositions of the solid phase caffeinates and p-coumarates were obtained on the basis of the amounts of hydrogen and carbon determined using an elemental analysis. The degree of hydration and the thermal decomposition of each compound were examined via a thermal analysis of TG, DTG, and DSC. Antioxidant spectroscopic tests were performed using the DPPH (1,1-diphenyl-2-picrylhydrazyl radical), FRAP (ferric reducing antioxidant activity), and ABTS (2,2’-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) (diammonium salt radical cation) methods. The antimicrobial activity of each compound against Escherichia coli, Bacillus subtilis, and Candida albicans was investigated. The electrical properties of the liposomes which mimicked the microbial surfaces formed in the electrolyte containing the tested compounds were also investigated. The above biological properties of the obtained complexes were compared with the activities of p-CAH2 and CFAH3. The obtained data suggest that lanthanide complexes are much more thermally stable and have higher antimicrobial and antioxidant properties than the ligands (with the exception of CFAH3 in the case of antioxidant activity tests). The Gd(III) complexes revealed the highest biological activity among the studied lanthanide complexes.pl
dc.description.sponsorshipNational Science Centre (NCN), Poland, under the research project number 2018/29/B/NZ9/01997.pl
dc.language.isoenpl
dc.publisherMDPIpl
dc.rightsAttribution-NoDerivatives 4.0 Międzynarodowe*
dc.rightsUznanie autorstwa 4.0 Międzynarodowe*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.subjectlanthanidespl
dc.subjectspectroscopic studypl
dc.subjectantioxidant propertiespl
dc.subjectantimicrobial propertiespl
dc.subjectp-coumaratespl
dc.subjectcaffeinatespl
dc.titleStructures, Antioxidant Properties, and Antimicrobial Properties of Eu(III), Gd(III), and Dy(III) Caffeinates and p-Coumaratespl
dc.typeArticlepl
dc.rights.holderCopyright: © 2023 by the authorspl
dc.rights.holderThis article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https:// creativecommons.org/licenses/by/ 4.0/).pl
dc.identifier.doi10.3390/molecules28186506-
dc.description.EmailGrzegorz Świderski: g.swiderski@pb.edu.plpl
dc.description.EmailWłodzimierz Lewandowski: w.lewandowski@pb.ed.plpl
dc.description.AffiliationGrzegorz Świderski - Department of Chemistry Biology and Biotechnology, Bialystok University of Technologypl
dc.description.AffiliationMonika Kalinowska - Department of Chemistry Biology and Biotechnology, Bialystok University of Technologypl
dc.description.AffiliationEwelina Gołębiewska - Department of Chemistry Biology and Biotechnology, Bialystok University of Technologypl
dc.description.AffiliationRenata Świsłocka - Department of Chemistry Biology and Biotechnology, Bialystok University of Technologypl
dc.description.AffiliationWłodzimierz Lewandowski - Department of Chemistry Biology and Biotechnology, Bialystok University of Technologypl
dc.description.AffiliationNatalia Kowalczyk - Department of Chemistry Biology and Biotechnology, Bialystok University of Technologypl
dc.description.AffiliationMonika Naumowicz - Department of Physical Chemistry, Faculty of Chemistry, University of Bialystokpl
dc.description.AffiliationAdam Cudowski - Department of Water Ecology, Faculty of Biology, University of Bialystokpl
dc.description.AffiliationAnna Pietryczuk - Department of Water Ecology, Faculty of Biology, University of Bialystokpl
dc.description.AffiliationEdyta Nalewajko-Sieliwoniuk - Department of Analytical Chemistry, Faculty of Chemistry, University of Bialystokpl
dc.description.AffiliationIzabela Wysocka - Department of Analytical Chemistry, Faculty of Chemistry, University of Bialystokpl
dc.description.AffiliationŻaneta Arciszewska - Department of Analytical Chemistry, Faculty of Chemistry, University of Bialystokpl
dc.description.AffiliationBeata Godlewska-Żyłkiewicz - Department of Analytical Chemistry, Faculty of Chemistry, University of Bialystokpl
dc.description.referencesCaparica, R.; Júlio, A.; Rolim, B.A.; Santos de Almeida, T.; Guilherme, C.J. In vitro cytotoxicity assessment of ferulic, caffeic and p-coumaric acids on human renal cancer cells. Biomed. Biopharm. Res. 2020, 17, 63–74pl
dc.description.referencesHeleno, S.A.; Martins, A.; Queiroz, M.J.R.; Ferreira, I.C. Bioactivity of phenolic acids: Metabolites versus parent compounds: A review. Food Chem. 2015, 173, 501–513.pl
dc.description.referencesStojković D.; Petrović, J.; Soković, M.; Glamočlija, J.; Kukić-Marković, J.; Petrović, S. In situ antioxidant and antimicrobial activities of naturally occurring caffeic acid, p-coumaric acid and rutin, using food systems. J. Sci. Food Agric. 2013, 93, 3205–3208.pl
dc.description.referencesMagnani, C.; Isaac, V.L.B.; Correa, M.A.; Salgado, H.R.N. Caffeic acid: A review of its potential use in medications and cosmetics. Anal. Methods 2014, 6, 3203–3210.pl
dc.description.referencesIsmail Kiliç, Yeşim Yeşiloğlu. Spectroscopic studies on the antioxidant activity of p-coumaric acid. Spectrochim. Acta Part A 2013, 115, 719–724.pl
dc.description.referencesDamasceno, S.S.; Dantas, B.B.; Ribeiro-Filho, J.; Araújo, A.M.; Costa, G.M. Chemical properties of caffeic and ferulic acids in biological system: Implications in cancer therapy. A review. Curr. Pharm. Des. 2017, 23, 3015–3023.pl
dc.description.referencesMirzaei, S.; Gholami, M.H.; Zabolian, A.; Saleki, H.; Farahani, M.V.; Hamzehlou, S.; Far, F.B.; Sharifadeh, S.O.; Samarghandian, S.; Khan, H.; et al. Caffeic acid and its derivatives as potential modulators of oncogenic molecular pathways: New hope in the fight against cancer. Pharmacol. Res. 2021, 171, 105759.pl
dc.description.referencesHu, X.; Yang, Z.; Liu, W.; Pan, Z.; Zhang, X.; Li, M.; Liu, X.; Zheng, Q.; Li, D. The anti-tumor effects of p-coumaric acid on melanoma A375 and B16 cells. Front. Oncol. 2020, 10, 558414.pl
dc.description.referencesMatsunaga, T.; Tsuchimura, S.; Azuma, N.; Endo, S.; Ichihara, K.; Ikari, A. Caffeic acid phenethyl ester potentiates gastric cancer cell sensitivity to doxorubicin and cisplatin by decreasing proteasome function. Anticancer Drug. 2019, 30, 251–259.pl
dc.description.referencesKoraneekit, A.; Limpaiboon, T.; Sangka, A.; Boonsiri, P.; Daduang, S.; Daduang, J. Synergistic effects of cisplatin-caffeic acid induces apoptosis in human cervical cancer cells via the mitochondrial pathways. Oncol. Lett. 2018, 15, 7397–7402.pl
dc.description.referencesKhan, F.; Bamunuarachchi, N.I.; Tabassum, N.; Kim, Y.M. Caffeic acid and its derivatives: Antimicrobial drugs toward microbial pathogens. J. Agric. Food Chem. 2021, 69, 2979–3004.pl
dc.description.referencesGenaro-Mattos, T.C.; Maurício, Â.Q.; Rettori, D.; Alonso, A.; Hermes-Lima, M. Antioxidant activity of caffeic acid against iron-induced free radical generation—A chemical approach. PLoS ONE 2015, 10, e0142402.pl
dc.description.referencesEspíndola, K.M.M.; Ferreira, R.G.; Narvaez, L.E.M.; Silva Rosario, A.C.R.; Da Silva, A.H.M.; Silva, A.G.B.; Vieira, A.P.O.; Monteiro, M.C. Chemical and pharmacological aspects of caffeic acid and its activity in hepatocarcinoma. Front. Oncol. 2019, 21, 541.pl
dc.description.referencesPavlíková, N. Caffeic acid and diseases—Mechanisms of action. Int. J. Mol. Sci. 2022, 24, 588.pl
dc.description.referencesKhatkar, A.; Nanda, A.; Kumar, P.; Narasimhan, B. Synthesis, antimicrobial evaluation and QSAR studies of p-coumaric acid derivatives. Arab. J. Chem. 2017, 10, 3804–3815.pl
dc.description.referencesTosovic, J. Spectroscopic features of caffeic acid: Theoretical study. Kragujev. J. Sci. 2017, 29, 99–108.pl
dc.description.referencesShen, Y.; Song, X.; Li, L.; Sun, J.; Jaiswal, Y.; Huang, J.; Liu, C.; Yang, W.; Williams, L.; Zhang, H.; et al. Protective effects of p-coumaric acid against oxidant and hyperlipidemia-an in vitro and in vivo evaluation. Biomed. Pharmacother. 2019, 111, 579–587.pl
dc.description.referencesZhu, H.; Liang, Q.H.; Xiong, X.G.; Wang, Y.; Zhang, Z.H.; Sun, M.J.; Lu, X.; Wu, D. Anti-inflammatory effects of p-coumaric acid, a natural compound of Oldenlandia diffusa, on arthritis model rats. Evid. Based Complement. Alternat. Med. 2018, 2018, 5198594.pl
dc.description.referencesArciszewska, Z.; Gama, S.; Kalinowska, M.; Świderski, G.; Świsłocka, R.; Gołębiewska, E.; Naumowicz, M.; Worobiczuk, M.; Cudowski, A.; Pietryczuk, A.; et al. Caffeic Acid/Eu (III) complexes: Solution equilibrium studies, structure characterization and biological activity. Int. J. Mol. Sci. 2022, 23, 888.pl
dc.description.referencesŚwiderski, G.; Jabłońska-Trypuć, A.; Kalinowska, M.; Świsłocka, R.; Karpowicz, D.; Magnuszewska, M.; Lewandowski, W. Spectroscopic, theoretical and antioxidant study of 3d-transition metals (Co (II), Ni (II), Cu (II), Zn (II)) complexes with cichoric acid. Materials 2020, 13, 3102.pl
dc.description.referencesKalinowska, M.; Sienkiewicz-Gromiuk, J.; Swiderski, G.; Pietryczuk, A.; Cudowski, A.; Lewandowski, W. Zn(II) Complex of Plant Phenolic Chlorogenic Acid: Antioxidant, Antimicrobial and Structural Studies. Materials 2020, 13, 3745.pl
dc.description.referencesKalinowska, M.; Mazur, L.; Piekut, J.; Rzączyńska, Z.; Laderiere, B.; Lewandowski, W. Synthesis, crystal structure, spectroscopic properties, and antimicrobial studies of a zinc(II) complex of p-coumaric acid. J. Coord. Chem. 2013, 66, 334–344.pl
dc.description.referencesLewandowski, W.; Kalinowska, M.; Lewandowska, H. The influence of metals on the electronic system of biologically important ligands. Spectroscopic study of benzoates, salicylates, nicotinates and isoorotates. Review. J. Inorg. Biochem. 2005, 99, 1407–1423.pl
dc.description.referencesJabłońska-Trypuć, A.; Wydro, U.; Wołejko, E.; Swiderski, G.; Lewandowski, W. Biological Activity of New Cichoric Acid–Metal Complexes in Bacterial Strains, Yeast-Like Fungi, and Human Cell Cultures In Vitro. Nutrients 2020, 12, 154.pl
dc.description.referencesSamsonowicz, M.; Regulska, E.; Kalinowska, M. Hydroxyflavone metal complexes-molecular structure, antioxidant activity and biological effects. Chem. Biol. Interact. 2017, 273, 245–256.pl
dc.description.referencesKaczmarek, M.T.; Zabiszak, M.; Nowak, M.; Jastrzab, R. Lanthanides: Schiff base complexes, applications in cancer diagnosis, therapy, and antibacterial activity. Coord. Chem. Rev. 2018, 370, 42–54.pl
dc.description.referencesFricker, S.P. The therapeutic application of lanthanides. Chem. Soc. Rev. 2006, 35, 524–533.pl
dc.description.referencesChundawat, N.S.; Jadoun, S.; Zarrintaj, P.; Chauhan, N.P.S. Lanthanide complexes as anticancer agents: A review. Polyhedron 2021, 207, 115387.pl
dc.description.referencesCatalano, A.; Sinicropi, M.S.; Iacopetta, D.; Ceramella, J.; Mariconda, A.; Rosano, C.; Scali, E.; Saturnino, C.; Longo, P. A review on the advancements in the field of metal complexes with Schiff bases as antiproliferative agents. Appl. Sci. 2021, 11, 6027pl
dc.description.referencesMadanhire, T.; Davids, H.; Pereira, M.C.; Hosten, E.C.; Abrahams, A.R. Synthesis, characterisation and anticancer activity screening of lanthanide (III) acetate complexes with benzohydrazone and nicotinohydrazone ligands. Polyhedron 2020, 184, 114560.pl
dc.description.referencesZhao, Q.; Zhu, M.; Zhang, J. A series of novel lanthanide complexes with 2-bromine-5-methoxybenzoic acid and 2,20-bipyridine: Syntheses, crystal structures, and luminescent properties. J. Mol. Struct. 2017, 1149, 171–182.pl
dc.description.referencesZheng, J.; Ren, S.; Ren, N.; Zhang, J.; Zhang, D.; Wang, S. Synthesis, thermodynamic properties and antibacterial activities oflanthanide complexes with 3,5-dimethoxybenzoic acid and 1,10-phenanthroline. Thermochim. Acta 2013, 572, 101–106.pl
dc.description.referencesŚwisłocka, R.; Kowczyk-Sadowy, M.; Kalinowska, M.; Lewandowski, W. Spectroscopic (FT-IR, FT-Raman, 1H and 13C NMR) and theoretical studies of p-coumaric acid and alkali metal p-coumarates. J. Spectroscop. 2012, 27, 35–48.pl
dc.description.referencesŚwisłocka, R. Spectroscopic (FT-IR, FT-Raman, UV absorption, 1H and 13C NMR) and theoretical (in B3LYP/6-311++ G** level) studies on alkali metal salts of caffeic acid. Spectrochim. Acta Part A 2013, 100, 21–30.pl
dc.description.referencesVarsányi, G. Assignments for Vibrational Spectra of 700 Benzene Derivates; Akademiai Kiado: Budapest, Hungary, 1973.pl
dc.description.referencesNakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part B: Applications in Coordination, Organometallic, and Bioinorganic Chemistry; Deacon, G.B., Philips, R.J., Eds.; John Wiley & Sons: Hoboken, NJ, USA, 2009.pl
dc.description.referencesLitwinienko, G.; Ingold, K.U. Abnormal Solvent Effects on Hydrogen Atom Abstraction. 2. Resolution of the Curcumin Antioxidant Controversy. The Role of Sequential Proton Loss Electron Transfer. J. Org. Chem. 2004, 69, 5888–5896.pl
dc.description.referencesNalewajko-Sieliwoniuk, E.; Gama, S.; Arciszewska, Z.; Bogdan, P.; Naumowicz, M.; Kalinowska, M.; Świderski, G.; Świsłocka, R.; Lewandowski, W.; Lando, G.; et al. Chemical speciation of caffeic and p-coumaric acids with selected lanthanides. J. Mol. Liq. 2023, 382, 121915.pl
dc.description.referencesKalinowska, M.; Gołębiewska, E.; Mazur, L.; Lewandowska, H.; Pruszyński, M.; Swiderski, G.; Wyrwas, M.; Pawluczuk, N.; Lewandowski, W. Crystal structure, spectroscopic characterization, antioxidant and cytotoxic activity of new Mg(II) and Mn(II)/Na(I) complexes of isoferulic acid. Materials 2021, 14, 3236.pl
dc.description.referencesEl-Lateef, H.M.A.; El-Dabea, T.; Khalaf, M.M.; Abu-Dief, A.M. Recent Overview of Potent Antioxidant Activity of Coordination Compounds. Antioxidants 2023, 12, 213.pl
dc.description.referencesArendrup, M.C.; Patterson, T.F. Multidrug-resistant Candida: Epidemiology, molecular mechanisms, and treatment. J. Infect. Dis. 2017, 216, 445–451.pl
dc.description.referencesCosta-de-Oliveira, S.; Rodrigues, A.G. Candida albicans antifungal resistance and tolerance in bloodstream infections: The triad yeast-host-antifungal. Microorganisms 2020, 8, 154.pl
dc.description.referencesBreijyeh, Z.; Jubeh, B.; Karaman, R. Resistance of Gram-Negative bacteria to current antibacterial agents and approaches to resolve it. Molecules 2020, 25, 1340.pl
dc.description.referencesZhou, X.; Zhao, Y.; Dai, L.; Xu, G. Bacillus subtilis and Bifidobacteria bifidum Fermentation Effects on Various Active Ingredient Contents in Cornus officinalis Fruit. Molecules 2023, 28, 1032.pl
dc.description.referencesFrei, A. Metal Complexes, an Untapped Source of Antibiotic Potential? Antibiotics 2020, 9, 90.pl
dc.description.referencesDenning, E.J.; Beckstein, O. Influence of lipids on protein mediated transmembrane transport. Chem. Phys. Lipids 2013, 169, 57–71.pl
dc.description.referencesOursel, D.; Loutelier-Bourhis, C.; Orange, N.; Chevalier, S.; Norris, V.; Lange, C.M. Lipid composition of membranes of Escherichia coli by liquid chromatography/tandem mass spectrometry using negative electrospray ionization. Rapid Commun. Mass Spectrom. 2007, 21, 1721–1728.pl
dc.description.referencesSantos, A.X.; Riezman, H. Yeast as a model system for studying lipid homeostasis and function. FEBS Lett. 2012, 586, 2858–2867pl
dc.description.referencesMartin, C.E.; Oh, C.S.; Jiang, Y. Regulation of long chain unsaturated fatty acid synthesis in yeast. Biochim. Biophys. Acta 2007, 1771, 271–285.pl
dc.description.referencesZinser, E.; Sperka-Gottlieb, C.D.; Fasch, E.V.; Kohlwein, S.D.; Paltauf, F.; Daum, G. Phospholipid synthesis and lipid composition of subcellular membranes in the unicellular eukaryote Saccharomyces cerevisiae. J. Bacteriol. 1991, 173, 2026–2034.pl
dc.description.referencesLöffler, J.; Einsele, H.; Hebart, H.; Schumacher, U.; Hrastnik, C.; Daum, G. Phospholipid and sterol analysis of plasma membranes of azole-resistant Candida albicans strains. FEMS Microbiol. Lett. 2000, 185, 59–63.pl
dc.description.referencesArakha, M.; Saleem, M.; Mallick, B.; Jha, S. The effects of interfacial potential on antimicrobial propensity of ZnO nanoparticle. Sci. Rep. 2015, 5, 9578.pl
dc.description.referencesChibowski, E.; Szcze´s, A. Zeta potential and surface charge of DPPC and DOPC liposomes in the presence of PLC enzyme. Adsorption 2016, 22, 755–765.pl
dc.description.referencesHuang, C. Studies on phosphatidylcholine vesicles. Formation and physical characteristics. Biochemistry 1969, 8, 344–352.pl
dc.description.referencesKotyńska, J.; Naumowicz, M. Theoretical considerations and the microelectrophoresis experiment on the influence of selected chaotropic anions on phosphatidylcholine membrane surface charge density. Molecules 2020, 25, 132.pl
dc.description.referencesAlexander, A.E.; Johnson, P. Colloid Science. J. Pol. Sci. 1949, 4, 747–748.pl
dc.identifier.eissn1420-3049-
dc.description.volume28pl
dc.description.issue18pl
dc.description.number6506pl
dc.description.firstpage1pl
dc.description.lastpage25pl
dc.identifier.citation2Moleculespl
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