{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,23]],"date-time":"2026-08-23T17:03:15Z","timestamp":1787504595268,"version":"build-2736575974"},"reference-count":97,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2022,1,27]],"date-time":"2022-01-27T00:00:00Z","timestamp":1643241600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Microorganisms are able to give rise to biofilm formation on food matrixes and along food industry infrastructures or medical equipment. This growth may be reduced by the application of molecules preventing bacterial adhesion on these surfaces. A new Schiff base ligand, derivative of hesperetin, HABH (2-amino-N\u2032-(2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-ylidene)benzohydrazide), and its copper complex, CuHABH [CuLH2(OAc)], were designed, synthesized and analyzed in terms of their structure and physicochemical properties, and tested as antibacterial agents. Their structures both in a solid state and in solution were established using several methods: FT-IR, 1H NMR, 13C NMR, UV-Vis, FAB MS, EPR, ESI-MS and potentiometry. Coordination binding of the copper(II) complex dominating at the physiological pH region in the solution was found to be the same as that detected in the solid state. Furthermore, the interaction between the HABH and CuHABH with calf-thymus DNA (CT-DNA) were investigated. These interactions were tracked by UV-Vis, CD (circular dichroism) and spectrofluorimetry. The results indicate a stronger interaction of the CuHABH with the CT-DNA than the HABH. It can be assumed that the nature of the interactions is of the intercalating type, but in the high concentration range, the complex can bind to the DNA externally to phosphate residues or to a minor\/major groove. The prepared compounds possess antibacterial and antibiofilm activities against Gram-positive and Gram-negative bacteria. Their antagonistic activity depends on the factor-strain test system. The glass was selected as a model surface for the experiments on antibiofilm activity. The adhesion of bacterial cells to the glass surface in the presence of the compounds was traced by luminometry and the best antiadhesive action against both bacterial strains was detected for the CuHABH complex. This molecule may play a crucial role in disrupting exopolymers (DNA\/proteins) in biofilm formation and can be used to prevent bacterial adhesion especially on glass equipment.<\/jats:p>","DOI":"10.3390\/molecules27030845","type":"journal-article","created":{"date-parts":[[2022,1,27]],"date-time":"2022-01-27T22:00:56Z","timestamp":1643320856000},"page":"845","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["From the Physicochemical Characteristic of Novel Hesperetin Hydrazone to Its In Vitro Antimicrobial Aspects"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1989-5989","authenticated-orcid":false,"given":"Anna","family":"Syku\u0142a","sequence":"first","affiliation":[{"name":"Institute of Natural Products and Cosmetics, Faculty of Biotechnology and Food Sciences, Lodz University of Technology, 90-537 \u0141\u00f3d\u017a, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"El\u017cbieta","family":"\u0141odyga-Chru\u015bci\u0144ska","sequence":"additional","affiliation":[{"name":"Institute of Natural Products and Cosmetics, Faculty of Biotechnology and Food Sciences, Lodz University of Technology, 90-537 \u0141\u00f3d\u017a, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7229-5966","authenticated-orcid":false,"given":"Eugenio","family":"Garribba","sequence":"additional","affiliation":[{"name":"Department of Medical, Surgical and Experimental Sciences, University of Sassari, Viale San Pietro, I-07100 Sassari, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4006-6464","authenticated-orcid":false,"given":"Dorota","family":"Kr\u0119giel","sequence":"additional","affiliation":[{"name":"Department of Environmental Biotechnology, Faculty of Biotechnology and Food Sciences, Lodz University of Technology, 90-530 \u0141\u00f3d\u017a, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aliaksandr","family":"Dzeikala","sequence":"additional","affiliation":[{"name":"Institute of Natural Products and Cosmetics, Faculty of Biotechnology and Food Sciences, Lodz University of Technology, 90-537 \u0141\u00f3d\u017a, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3958-0407","authenticated-orcid":false,"given":"El\u017cbieta","family":"Klewicka","sequence":"additional","affiliation":[{"name":"Institute of Fermentation Technology and Microbiology, Faculty of Biotechnology and Food Sciences, Lodz University of Technology, 90-530 \u0141\u00f3d\u017a, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lidia","family":"Piekarska-Radzik","sequence":"additional","affiliation":[{"name":"Institute of Fermentation Technology and Microbiology, Faculty of Biotechnology and Food Sciences, Lodz University of Technology, 90-530 \u0141\u00f3d\u017a, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,1,27]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"898","DOI":"10.3389\/fmicb.2018.00898","article-title":"Biofilms in the Food Industry: Health Aspects and Control Methods","volume":"9","author":"Villar","year":"2018","journal-title":"Front. Microbiol."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"453","DOI":"10.1007\/s00203-014-0983-1","article-title":"Biofilm formation and persistence on abiotic surfaces in the context of food and medical environments","volume":"196","author":"Abdallah","year":"2014","journal-title":"Arch. Microbiol."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Colagiorgi, A., Bruini, I., Di Ciccio, P.A., Zanardi, E., Ghidini, S., and Ianieri, A. (2017). Listeria monocytogenes Biofilms in the Wonderland of Food Industry. Pathogens, 6.","DOI":"10.3390\/pathogens6030041"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"72","DOI":"10.1089\/mdr.2018.0027","article-title":"Relationship Between Biofilm Formation and Antimicrobial Resistance in Gram-Negative Bacteria","volume":"25","author":"Cepas","year":"2019","journal-title":"Microb. Drug Resist."},{"key":"ref_5","first-page":"51","article-title":"Biofilm-related disease","volume":"16","year":"2017","journal-title":"Expert Rev. Anti-Infect. Ther."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"276","DOI":"10.1093\/femsre\/fux010","article-title":"Molecular mechanisms of biofilm-based antibiotic resistance and tolerance in pathogenic bacteria","volume":"41","author":"Hall","year":"2017","journal-title":"FEMS Microbiol. Rev."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1061","DOI":"10.2217\/fmb.12.76","article-title":"Biofilm-specific antibiotic resistance","volume":"7","author":"Mah","year":"2012","journal-title":"Futur. Microbiol."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"431","DOI":"10.1111\/dgd.12627","article-title":"Dependence of the Bacillus subtilis biofilm expansion rate on phenotypes and the morphology under different growing conditions","volume":"61","author":"Wang","year":"2019","journal-title":"Dev. Growth Differ."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Ullah, A., Munir, S., Badshah, S.L., Khan, N., Ghani, L., Poulson, B.G., Emwas, A.-H., and Jaremko, M. (2020). Important Flavonoids and Their Role as a Therapeutic Agent. Molecules, 25.","DOI":"10.3390\/molecules25225243"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"522","DOI":"10.1080\/21505594.2017.1313372","article-title":"Strategies for combating bacterial biofilms: A focus on anti-biofilm agents and their mechanisms of action","volume":"9","author":"Roy","year":"2018","journal-title":"Virulence"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"103093","DOI":"10.1016\/j.bioorg.2019.103093","article-title":"Amino acids conjugated quinazolinone-Schiff\u2019s bases as potential antimicrobial agents: Synthesis, SAR and molecular docking studies","volume":"90","author":"Rakesh","year":"2019","journal-title":"Bioorganic Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"571","DOI":"10.1007\/s10534-018-0106-6","article-title":"5-Nitroimidazole-derived Schiff bases and their copper(II) complexes exhibit potent antimicrobial activity against pathogenic anaerobic bacteria","volume":"31","author":"Oliveira","year":"2018","journal-title":"BioMetals"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"790","DOI":"10.1007\/s00044-013-0672-7","article-title":"Synthesis and anti-biofilm activity of thiazole Schiff bases","volume":"23","author":"More","year":"2013","journal-title":"Med. Chem. Res."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"642","DOI":"10.1016\/j.saa.2018.05.057","article-title":"Synthesis, spectral and antimicrobial studies of amino acid derivative Schiff base metal (Co, Mn, Cu, and Cd) complexes","volume":"206","author":"Pervaiz","year":"2018","journal-title":"Spectrochim. Acta A Mol. Biomol. Spectrosc."},{"key":"ref_15","first-page":"963","article-title":"Structural investigation of some novel synthesized Schiff base Transition metal complexes derived from drug together with Antimicrobial study","volume":"32","author":"Mumtaz","year":"2019","journal-title":"Pak. J. Pharm. Sci."},{"key":"ref_16","first-page":"1","article-title":"Antifungal and Antioxidant Activities of Pyrrolidone Thiosemicarbazone Complexes","volume":"2012","author":"Kadhum","year":"2012","journal-title":"Bioinorg. Chem. Appl."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"34","DOI":"10.1016\/j.jinorgbio.2014.11.005","article-title":"Chelating ability and biological activity of hesperetin Schiff base","volume":"143","author":"Symonowicz","year":"2015","journal-title":"J. Inorg. Biochem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"36","DOI":"10.1016\/j.jinorgbio.2016.09.014","article-title":"Coordination ability and biological activity of a naringenin thiosemicarbazone","volume":"165","author":"Brodowska","year":"2016","journal-title":"J. Inorg. Biochem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1020","DOI":"10.1111\/iej.13093","article-title":"Inflammatory potential of monospecies biofilm matrix components","volume":"52","author":"Ramirez","year":"2019","journal-title":"Int. Endod. J."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1128\/microbiolspec.MB-0004-2014","article-title":"Biofilm Matrix Proteins","volume":"3","author":"Fong","year":"2015","journal-title":"Microbiol. Spectr."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1284","DOI":"10.3389\/fmicb.2019.01284","article-title":"Composition of the Biofilm Matrix of Cutibacterium acnes Acneic Strain RT5","volume":"10","author":"Gannesen","year":"2019","journal-title":"Front. Microbiol."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"4823","DOI":"10.1016\/j.ica.2009.07.008","article-title":"DNA binding affinity and antioxidative activity of copper(II) and zinc(II) complexes with a novel hesperetin Schiff base ligand","volume":"362","author":"Li","year":"2009","journal-title":"Inorg. Chim. Acta"},{"key":"ref_23","doi-asserted-by":"crossref","unstructured":"Syku\u0142a, A. (2021). Kowalska-Baron, K. Ga\u0142\u0119cki, P. B\u0142azi\u0144ska, E. \u0141odyga-Chru\u015bci\u0144ska, Structural and Spectral Investigation of a Series of Flavanone Derivatives. Molecules, 26.","DOI":"10.3390\/molecules26051298"},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Gans, P., Sabatini, A., and Vacca, A. (1985). SUPERQUAD: An improved general program for computation of formation constants from potentiometric data. J. Chem. Soc. Dalton Trans., 1195\u20131200.","DOI":"10.1039\/dt9850001195"},{"key":"ref_25","unstructured":"(2022, January 26). WinEPR SimFonia, Version 1.25. Bruker Analytische Messtechnik GmbH: Karlshrue. Available online: https:\/\/www.bruker.com\/en\/products-and-solutions\/mr\/epr-instruments\/epr-software\/winepr.html."},{"key":"ref_26","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., and Petersson, G.A. (2022, January 26). Fox Gaussian 09, Available online: https:\/\/gaussian.com."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"5648","DOI":"10.1063\/1.464913","article-title":"Density-functional thermochemistry. III. The role of exact exchange","volume":"98","author":"Becke","year":"1993","journal-title":"J. Chem. Phys."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1103\/PhysRevB.37.785","article-title":"Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density","volume":"37","author":"Lee","year":"1988","journal-title":"Phys. Rev. B"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1282","DOI":"10.1021\/ct6001187","article-title":"Geometries of Transition-Metal Complexes from Density-Functional Theory","volume":"2","author":"Kabrede","year":"2006","journal-title":"J. Chem. Theory Comput."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1449","DOI":"10.1021\/ct800172j","article-title":"Geometries of Third-Row Transition-Metal Complexes from Density-Functional Theory","volume":"4","author":"Buehl","year":"2008","journal-title":"J. Chem. Theory Comput."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"2486","DOI":"10.1002\/qua.23237","article-title":"The effect of the functional, basis set, and solvent in the simulation of the geometry and spectroscopic properties of V","volume":"112","author":"Micera","year":"2012","journal-title":"Int. J. Quantum Chem."},{"key":"ref_32","unstructured":"Neese, F. (2022, January 26). ORCA \u2013 An Ab Initio, DFT and Semiempirical Program Package, Version 4.0, Max-Planck-Institute for Chemical Energy Conversion, M\u00fclheim a. d. Ruhr. Available online: https:\/\/orcaforum.kofo.mpg.de\/app.php\/portal."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"e1327","DOI":"10.1002\/wcms.1327","article-title":"Software update: The ORCA program system, version 4.0","volume":"8","author":"Neese","year":"2018","journal-title":"Wiley Interdiscip. Rev. Comput. Mol. Sci."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"224108","DOI":"10.1063\/5.0004608","article-title":"The ORCA quantum chemistry program package","volume":"152","author":"Neese","year":"2020","journal-title":"J. Chem. Phys."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"3865","DOI":"10.1103\/PhysRevLett.77.3865","article-title":"Generalized gradient approximation made simple","volume":"77","author":"Perdew","year":"1996","journal-title":"Phys. Rev. Lett."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1396","DOI":"10.1103\/PhysRevLett.78.1396","article-title":"Generalized Gradient Approximation Made Simple [Phys. Rev. Lett. 77, 3865 (1996)]","volume":"78","author":"Perdew","year":"1997","journal-title":"Phys. Rev. Lett."},{"key":"ref_37","doi-asserted-by":"crossref","unstructured":"Sciortino, G., Lubinu, G., Mar\u00e9chal, J.-D., and Garribba, E. (2018). DFT Protocol for EPR Prediction of Paramagnetic Cu(II) Complexes and Application to Protein Binding Sites. Magnetochemistry, 4.","DOI":"10.3390\/magnetochemistry4040055"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"6392","DOI":"10.1021\/bi00394a013","article-title":"Mechan, Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA","volume":"26","author":"Wolfe","year":"1987","journal-title":"Biochemistry"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"2511","DOI":"10.1016\/S0968-0896(01)00243-7","article-title":"Thiazole orange as the fluorescent intercalator in a high resolution fid assay for determining DNA binding affinity and sequence selectivity of small molecules","volume":"9","author":"Boger","year":"2001","journal-title":"Bioorg. Med. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Lakowicz, J.R. (2006). Principles of Fluorescence Spectroscopy, Springer. [3rd ed.].","DOI":"10.1007\/978-0-387-46312-4"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"53","DOI":"10.1007\/0-306-47058-6_2","article-title":"Fluorescence Quenching: Theory and Applications","volume":"Volume 2","author":"Lakowicz","year":"2002","journal-title":"Topics in Fluorescence Spectroscopy"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"555","DOI":"10.1007\/s10895-006-0091-y","article-title":"Fluorescence Resonance Energy Transfer and Complex Formation between Thiazole Orange and Various Dye-DNA Conjugates: Implications in Signaling Nucleic Acid Hybridization","volume":"16","author":"Algar","year":"2006","journal-title":"J. Fluoresc."},{"key":"ref_43","unstructured":"EUCAST (2021, November 26). EUCAST Disk Diffusion Test Methodology. Available online: https:\/\/www.eucast.org\/ast_of_bacteria\/disk_diffusion_methodology\/."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"562","DOI":"10.1016\/j.indcrop.2012.08.004","article-title":"Chemical composition and antibacterial properties of stem and leaf extracts from Ginja cherry plant","volume":"43","author":"Piccirillo","year":"2012","journal-title":"Ind. Crop. Prod."},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Kregiel, D., Rygala, A., Kolesinska, B., Nowacka, M., Herc, A.S., and Kowalewska, A. (2019). Antimicrobial and Antibiofilm N-acetyl-L-cysteine Grafted Siloxane Polymers with Potential for Use in Water Systems. Int. J. Mol. Sci., 20.","DOI":"10.3390\/ijms20082011"},{"key":"ref_46","first-page":"305","article-title":"Effect of starvation stress on morphological changes and production of adhesive exopolysaccharide (EPS) by Proteus vulgaris","volume":"10","author":"Myszka","year":"2011","journal-title":"Acta Sci. Pol. Technol. Aliment."},{"key":"ref_47","first-page":"190","article-title":"Mononuclear Metal (II) Schiff Base complexes derived from thiazole and o-vanillin moieties: Synthesis, characterization, Thermal Behaviour and Biological Evaluation","volume":"31","author":"Nagesh","year":"2015","journal-title":"Int. J. Pharm. Sci. Rev. Res."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1102","DOI":"10.1016\/j.saa.2005.04.007","article-title":"Electronic, EPR, magnetic and mass spectral studies of mono and homo-binuclear Co(II) and Cu(II) complexes with a novel macrocyclic ligand","volume":"62","author":"Chandra","year":"2005","journal-title":"Spectrochim. Acta Part. A Mol. Biomol. Spectrosc."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"691","DOI":"10.1016\/0003-9861(74)90298-7","article-title":"Structural implications derived from the analysis of electron paramagnetic resonance spectra of natural and artificial copper proteins","volume":"165","author":"Peisach","year":"1974","journal-title":"Arch. Biochem. Biophys."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"1229","DOI":"10.1021\/ed083p1229","article-title":"The Determination of the Geometry of Cu(II) Complexes: An EPR Spectroscopy Experiment","volume":"83","author":"Garribba","year":"2006","journal-title":"J. Chem. Educ."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1007\/BF03163102","article-title":"Studies of EPR and ENDOR spectra of14N and15N label bis(2-hydroxyacetophenyl ketoxime)-63Cu(II) and-65Cu(II) complexes in disordered system","volume":"10","author":"Xu","year":"1996","journal-title":"Appl. Magn. Reson."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"608","DOI":"10.1021\/ic960604x","article-title":"EPR Spectra, Luminescence Data, and Radiationless Decay Processes of Copper(II) Porphyrins","volume":"36","author":"Cunningham","year":"1997","journal-title":"Inorg. Chem."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"3617","DOI":"10.1016\/S0277-5387(99)00291-0","article-title":"Copper(II) complexes with derivatives of salen and tetrahydrosalen: A spectroscopic, electrochemical and structural study","volume":"18","author":"Klement","year":"1999","journal-title":"Polyhedron"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"6227","DOI":"10.1021\/ic8001459","article-title":"Synthesis of Two New Linear Trinuclear CuIIComplexes: Mechanism of Magnetic Coupling through Hybrid B3LYP Functional and CShM Studies","volume":"47","author":"Thakurta","year":"2008","journal-title":"Inorg. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"3939","DOI":"10.1063\/1.1540619","article-title":"Metal and ligand hyperfine couplings in transition metal complexes: The effect of spin\u2013orbit coupling as studied by coupled perturbed Kohn\u2013Sham theory","volume":"118","author":"Neese","year":"2003","journal-title":"J. Chem. Phys."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"3079","DOI":"10.1016\/S0277-5387(01)00918-4","article-title":"The effect of the ring size of fused chelates on the thermodynamic and spectroscopic properties of peptide complexes of copper(II)","volume":"20","author":"Sanna","year":"2001","journal-title":"Polyhedron"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"4565","DOI":"10.1039\/b710949k","article-title":"Metallo-intercalators and metallo-insertors","volume":"44","author":"Zeglis","year":"2007","journal-title":"Chem. Commun."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"3051","DOI":"10.1021\/ja00190a046","article-title":"Mixed-ligand complexes of ruthenium(II): Factors governing binding to DNA","volume":"111","author":"Pyle","year":"1989","journal-title":"J. Am. Chem. Soc."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"3687","DOI":"10.1021\/ic302196v","article-title":"DNA Binding and Anti-Cancer Activity of Redox-Active Heteroleptic Piano-Stool Ru(II), Rh(III), and Ir(III) Complexes Containing 4-(2-Methoxypyridyl)phenyldipyrromethene","volume":"52","author":"Gupta","year":"2013","journal-title":"Inorg. Chem."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"2540","DOI":"10.1039\/b418164f","article-title":"Artificial metallonucleases","volume":"36","author":"Mancin","year":"2005","journal-title":"Chem. Commun."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"558","DOI":"10.1562\/0031-8655(2001)0740558PPAPET2.0.CO2","article-title":"Photophysical Properties and Photoinduced Electron Transfer within Host-Guest Complexes of 5,10,15,20-Tetrakis(4-N-methylpyridyl)porphyrin with Water-soluble Calixarenes and Cyclodextrins","volume":"74","author":"Lang","year":"2007","journal-title":"Photochem. Photobiol."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"163","DOI":"10.1016\/S0162-0134(02)00378-1","article-title":"DNA-fiber EPR study of the orientation of Cu(II) complexes of 1,10-phenanthroline and its derivatives bound to DNA: Mono(phenanthroline)-copper(II) and its ternary complexes with amino acids","volume":"89","author":"Chikira","year":"2002","journal-title":"J. Inorg. Biochem."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"5710","DOI":"10.1021\/ja070025z","article-title":"Experimental and Computational Investigation of Unsymmetrical Cyanine Dyes: Understanding Torsionally Responsive Fluorogenic Dyes","volume":"129","author":"Silva","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"861","DOI":"10.1021\/bc000042c","article-title":"Concerted Intercalation and Minor Groove Recognition of DNA by a Homodimeric Thiazole Orange Dye","volume":"11","author":"Bunkenborg","year":"2000","journal-title":"Bioconjugate Chem."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1002\/(SICI)1097-0282(199807)46:1<39::AID-BIP4>3.0.CO;2-Z","article-title":"The interactions between the fluorescent dye thiazole orange and DNA","volume":"46","author":"Nygren","year":"1998","journal-title":"Biopolymers"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"201","DOI":"10.1562\/0031-8655(2002)075<0201:FPOOCT>2.0.CO;2","article-title":"Fluorescent properties of oligonucleo-tide-conjugated thiazole orange probes","volume":"75","author":"Privat","year":"2002","journal-title":"Photochem. Photobiol."},{"key":"ref_67","first-page":"123","article-title":"Progress in research on the genus Listeria","volume":"54","author":"Muskalska","year":"2015","journal-title":"Post. Mikrobiol."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"527","DOI":"10.1146\/annurev.mi.39.100185.002523","article-title":"The influence of environment on envelope properties affecting survival of bacteria in infections","volume":"39","author":"Brown","year":"1985","journal-title":"Ann. Rev. Microbiol."},{"key":"ref_69","first-page":"131","article-title":"Functional Advantages Conferred by Extracellular Prokaryotic Membrane Vesicles","volume":"23","author":"Manning","year":"2013","journal-title":"J. Mol. Microbiol. Biotechnol."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"3845","DOI":"10.1128\/AAC.01772-10","article-title":"Moraxella catarrhalisOuter Membrane Vesicles Carry \u03b2-Lactamase and Promote Survival ofStreptococcus pneumoniaeandHaemophilus influenzaeby Inactivating Amoxicillin","volume":"55","author":"Schaar","year":"2011","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_71","first-page":"123","article-title":"Active efflux as the multidrug resistance mechanism","volume":"63","author":"Grinholc","year":"2009","journal-title":"Postepy Hig Med Dosw."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"197","DOI":"10.1016\/j.bioorg.2017.08.004","article-title":"Tannic acid affects the phenotype of Staphylococcus aureus resistant totetracycline and erythromycin by inhibition of efflux pumps","volume":"74","author":"Tintino","year":"2017","journal-title":"Bioorganic Chemistry."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"22","DOI":"10.1016\/j.cimid.2018.03.001","article-title":"In vitro e in silico evaluation of the inhibition of Staphylococcus aureus efflux pumps by caffeic and gallic acid","volume":"57","author":"Tintino","year":"2018","journal-title":"Comp. Immunol. Microbiol. Infect. Dis."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"104370","DOI":"10.1016\/j.meegid.2020.104370","article-title":"Effect of hydroxyamines derived from lapachol and norlachol against Staphylococcus aureus strains carrying the NorA efflux pump","volume":"84","author":"Figueredo","year":"2020","journal-title":"Infect. Genet. Evol."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"405","DOI":"10.4103\/2221-1691.321130","article-title":"Antibacterial activity and inhibition against Staphylococcus aureus NorA efflux pump by ferulic acid and its esterified derivatives","volume":"11","author":"Menezes","year":"2021","journal-title":"Asian Pac. J. Trop. Biomed."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"157","DOI":"10.1007\/s10863-021-09886-4","article-title":"Enhancement of the antibiotic activity by quercetin against Staphylococcus aureus efflux pumps","volume":"53","author":"Tintino","year":"2021","journal-title":"J. Bioenerg. Biomembr."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"90","DOI":"10.1128\/aem.46.1.90-97.1983","article-title":"Surface thermodynamics of bacterial adhesion","volume":"46","author":"Absolom","year":"1983","journal-title":"Appl. Environ. Microbiol."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"111085","DOI":"10.1016\/j.colsurfb.2020.111085","article-title":"Adhesion of Sphingomonas sp. GY2B onto montmorillonite: A combination study by thermodynamics and the extended DLVO theory","volume":"192","author":"Ruan","year":"2020","journal-title":"Colloids Surf. B Biointerfaces"},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"179","DOI":"10.1111\/j.1574-6968.2007.00688.x","article-title":"icaand beyond: Biofilm mechanisms and regulation in Staphylococcus epidermidis and Staphylococcus aureus","volume":"270","year":"2007","journal-title":"FEMS Microbiol. Lett."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1038\/s41467-018-03446-y","article-title":"Asymmetric adhesion of rod-shaped bacteria controls microcolony morphogenesis","volume":"9","author":"Duvernoy","year":"2018","journal-title":"Nat. Commun."},{"key":"ref_81","first-page":"345","article-title":"Adhesion of Aeromonas hydrophila to glass surfaces modified with organosilanes","volume":"51","author":"Kregiel","year":"2013","journal-title":"Food Technol. Biotechnol."},{"key":"ref_82","doi-asserted-by":"crossref","unstructured":"Nowacka, M., Ryga\u0142a, A., Kr\u0119giel, D., and Kowalewska, A. (2021). New Antiadhesive Hydrophobic Polysiloxanes. Molecules, 26.","DOI":"10.3390\/molecules26040814"},{"key":"ref_83","doi-asserted-by":"crossref","unstructured":"S\u00e1nchez-L\u00f3pez, E., Gomes, D., Esteruelas, G., Bonilla, L., Lopez-Machado, A.L., Galindo, R., Cano, A., Espina, M., Ettcheto, M., and Camins, A. (2020). Metal-Based Nanoparticles as Antimicrobial Agents: An Overview. Nanomaterials, 10.","DOI":"10.3390\/nano10020292"},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1155\/2015\/720654","article-title":"The Effect of Charge at the Surface of Silver Nanoparticles on Antimicrobial Activity against Gram-Positive and Gram-Negative Bacteria: A Preliminary Study","volume":"2015","author":"Abbaszadegan","year":"2015","journal-title":"J. Nanomater."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"1450","DOI":"10.3762\/bjnano.11.129","article-title":"Antimicrobial metal-based nanoparticles: A review on their synthesis, types and antimicrobial action","volume":"11","author":"Correa","year":"2020","journal-title":"Beilstein J. Nanotechnol."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"4697","DOI":"10.1021\/acsomega.8b03076","article-title":"Copper Nanocluster-Doped Luminescent Hydroxyapatite Nanoparticles for Antibacterial and Antibiofilm Applications","volume":"4","author":"Simon","year":"2019","journal-title":"ACS Omega"},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"14049","DOI":"10.1021\/acsomega.9b01886","article-title":"Remarkable Effect of Jacalin in Diminishing the Protein Corona Interference in the Antibacterial Activity of Pectin-Capped Copper Sulfide Nanoparticles","volume":"4","author":"Subramaniyan","year":"2019","journal-title":"ACS Omega"},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"3727","DOI":"10.1128\/AAC.02316-13","article-title":"Copper Complexation Screen Reveals Compounds with Potent Antibiotic Properties against Methicillin-Resistant Staphylococcus aureus","volume":"58","author":"Haeili","year":"2014","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1038\/s41598-018-26483-5","article-title":"Antimicrobial and anti-biofilm activity of hexadentated macrocyclic complex of copper (II) derived from thiosemicarbazide against Staphylococcus aureus","volume":"8","author":"Brahma","year":"2018","journal-title":"Sci. Rep."},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"50","DOI":"10.1111\/j.1574-6968.2006.00147.x","article-title":"Inhibitory effects of cranberry polyphenols on formation and acidogenicity ofStreptococcus mutansbiofilms","volume":"257","author":"Duarte","year":"2006","journal-title":"FEMS Microbiol. Lett."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"393217","DOI":"10.1155\/2014\/393217","article-title":"Hesperidin inhibits inflammatory response induced by Aeromonas hydrophila infec-tion and alters CD4+\/CD8+ T cell ratio","volume":"2014","author":"Abuelsaad","year":"2014","journal-title":"Med. Inflamm."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"659","DOI":"10.3389\/fmicb.2017.00659","article-title":"The Anti-Adhesive Effect of Curcumin on Candida albicans Biofilms on Denture Materials","volume":"8","author":"Alalwan","year":"2017","journal-title":"Front. Microbiol."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"726","DOI":"10.1007\/s00284-012-0229-x","article-title":"Flavone Reduces the Production of Virulence Factors, Staphyloxanthin and \u03b1-Hemolysin, in Staphylococcus aureus","volume":"65","author":"Lee","year":"2012","journal-title":"Curr. Microbiol."},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"4819","DOI":"10.1128\/IAI.05580-11","article-title":"Apple Flavonoid Phloretin Inhibits Escherichia coli O157:H7 Biofilm Formation and Ameliorates Colon Inflammation in Rats","volume":"79","author":"Lee","year":"2011","journal-title":"Infect. Immun."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1038\/s41598-018-29291-z","article-title":"Curcumin alleviates persistence of Acinetobacter baumannii against colistin","volume":"8","author":"Kaur","year":"2018","journal-title":"Sci. Rep."},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"619","DOI":"10.1007\/s11240-019-01757-6","article-title":"Analysis of flavonoid content, antioxidant, antimicrobial and antibiofilm activity of in vitro hairy root extract of radish (Raphanus sativus L.)","volume":"140","author":"Muthusamy","year":"2020","journal-title":"Plant Cell Tissue Organ. Cult. (PCTOC)"},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"193","DOI":"10.1016\/j.micpath.2017.03.033","article-title":"Inhibitory effects of flavonoids on biofilm formation by Staphylococcus aureus that overexpresses efflux protein genes","volume":"107","author":"Lopes","year":"2017","journal-title":"Microb. Pathog."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/3\/845\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T22:08:52Z","timestamp":1760134132000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/3\/845"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,1,27]]},"references-count":97,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2022,2]]}},"alternative-id":["molecules27030845"],"URL":"https:\/\/doi.org\/10.3390\/molecules27030845","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,1,27]]}}}