REPOZYTORIUM UNIWERSYTETU
W BIAŁYMSTOKU
UwB

Proszę używać tego identyfikatora do cytowań lub wstaw link do tej pozycji: http://hdl.handle.net/11320/19912
Pełny rekord metadanych
Pole DCWartośćJęzyk
dc.contributor.authorBaryłka, Anna-
dc.contributor.authorSantonoceta, Giuseppina D.G.-
dc.contributor.authorGattuso, Giuseppe-
dc.contributor.authorGodlewska-Żyłkiewicz, Beata-
dc.contributor.authorSgarlata, Carmelo-
dc.contributor.authorMilea, Demetrio-
dc.contributor.authorGama, Sofia-
dc.date.accessioned2026-03-24T09:04:53Z-
dc.date.available2026-03-24T09:04:53Z-
dc.date.issued2025-
dc.identifier.citationJournal of Molecular Liquids, Vol. 417 (2025), 126671, p. 1-7pl
dc.identifier.issn0167-7322-
dc.identifier.urihttp://hdl.handle.net/11320/19912-
dc.description.abstractThe acid-base properties of 2-hydroxyquinoline (2-HQ), 4-hydroxyquinoline (4-HQ), 6-hydroxyquinoline (6-HQ), and 8-hydroxyquinoline (8-HQ) were investigated in this work by UV–Vis spectrophotometry, ISE-H+ potentiometry (glass electrode) and Isothermal Titration Calorimetry (ITC) in KCl(aq) at I = 0.2 mol⋅dm-3, and T = 298.15 K. Potentiometric titrations were also performed at different temperatures (288.15 ≤ T/K ≤ 318.15) to derive, together with direct ITC measurements, the corresponding protonation enthalpy and entropy changes. The analysis of the results obtained using various techniques allowed for a comprehensive characterization of the thermodynamic profile and chemical speciation of the studied hydroxyquinolines. Most importantly, it enabled the evaluation of how the position of the hydroxyl group influences the stability and driving forces involved in the protonation/deprotonation processes of both the quinolinic nitrogen and the hydroxyl groups on the pyridine or benzene ring of the hydroxyquinolines.pl
dc.description.sponsorshipThis research was funded by the National Science Centre (NCN), Poland, under the research project number 2020/39/B/ST4/03060 and National Recovery and Resilience Plan (NRRP), Mission 4, Component 2, Investment 1.1, Call for tender No. 1409 published on 14.9.2022 by the Italian Ministry of University and Research (MUR). Funded by the European Union – NextGenerationEU– Project Title Efficient Sequestration of Metal Ions from Aqueous Systems for Green and Sustainable Applications - AquaGreen – CUP J53D23014430001- Grant Assignment Decree No. 1409 adopted on 14/09/2022 by the Italian Ministry of University and Research (MUR).pl
dc.language.isoenpl
dc.publisherElsevierpl
dc.rightsUznanie autorstwa 4.0 Międzynarodowe*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.subjectHydroxyquinolinespl
dc.subjectThermodynamic parameterspl
dc.subjectpH potentiometrypl
dc.subjectIsothermal titration calorimetrypl
dc.subjectUV–Vis spectrophotometrypl
dc.titleAcid-base properties of hydroxyquinolines in aqueous solution: Effect of hydroxyl group position on thermodynamic protonation parameterspl
dc.typeArticlepl
dc.rights.holder© 2024 The Author(s). Published by Elsevier B.V.pl
dc.rights.holderThis is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/)pl
dc.identifier.doi10.1016/j.molliq.2024.126671-
dc.description.EmailCarmelo Sgarlata: sgarlata@unict.itpl
dc.description.EmailDemetrio Milea: dmilea@unime.itpl
dc.description.EmailSofia Gama: sofia.gama@ctn.tecnico.ulisboa.ptpl
dc.description.EmailAnna Baryłka: a.barylka@uwb.edu.plpl
dc.description.EmailBeata Godlewska-Żyłkiewicz: bgodlew@uwb.edu.plpl
dc.description.AffiliationAnna Baryłka - University of Bialystok, Doctoral School of Exact and Natural Sciencespl
dc.description.AffiliationGiuseppina D.G. Santonoceta - Dipartimento di Scienze Chimiche, Università degli Studi di Cataniapl
dc.description.AffiliationGiuseppe Gattuso - Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali, CHIBIOFARAM, Università degli Studi di Messinapl
dc.description.AffiliationBeata Godlewska-Żyłkiewicz - Department of Analytical and Inorganic Chemistry, Faculty of Chemistry, University of Bialystokpl
dc.description.AffiliationCarmelo Sgarlata - Dipartimento di Scienze Chimiche, Università degli Studi di Cataniapl
dc.description.AffiliationDemetrio Milea - Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali, CHIBIOFARAM, Università degli Studi di Messinapl
dc.description.AffiliationSofia Gama - Department of Analytical and Inorganic Chemistry, Faculty of Chemistry, University of Bialystok / Centro de Ciências e Tecnologias Nucleares, Instituto Superior Técnico, Universidade de Lisboapl
dc.description.referencesC. Sgarlata, G. Arena, R.P. Bonomo, A. Giuffrida, G. Tabbi, Simple and mixed complexes of copper(II) with 8-hydroxyquinoline derivatives and amino acids: Characterization in solution and potential biological implications, J. Inorg. Biochem. 180 (2018) 89.pl
dc.description.referencesS.H. Chan, C.H. Chui, S.W. Chan, S.H. Kok, D. Chan, M.Y. Tsoi, P.H. Leung, A.K. Lam, A.S. Chan, K.H. Lam, J.C. Tang, Synthesis of 8-hydroxyquinoline derivatives as novel antitumor agents, ACS Med. Chem. Lett. 4 (2013) 170–174.pl
dc.description.referencesM. Kubanik, H. Holtkamp, T. Söhnel, S.M.F. Jamieson, C.G. Hartinger, Impact of the Halogen Substitution Pattern on the Biological Activity of Organoruthenium 8-Hydroxyquinoline Anticancer Agents, Organometallics 34 (2015) 5658–5668.pl
dc.description.referencesV. Prachayasittikul, S. Prachayasittikul, S. Ruchirawat, V. Prachayasittikul, 8-Hydroxyquinolines: a review of their metal chelating properties and medicinal applications, Drug Des. Devel. Ther. 7 (2013), pp. 1157-1178.pl
dc.description.referencesP. Yadav, K. Shah, Quinolines, a perpetual, multipurpose scaffold in medicinal chemistry, Bioorg. Chem. 109 (2021) 104639.pl
dc.description.referencesA. Weyesa, E. Mulugeta, Recent advances in the synthesis of biologically and pharmaceutically active quinoline and its analogues: a review, RSC Adv. 10 (2020) 20784–20793.pl
dc.description.referencesS. Madapa, Z. Tusi, D. Sridhar, A. Kumar, M.I. Siddiqi, K. Srivastava, A. Rizvi, R. Tripathi, S.K. Puri, G.B. Shiva Keshava, P.K. Shukla, S. Batra, Search for new pharmacophores for antimalarial activity. Part I: synthesis and antimalarial activity of new 2-methyl-6-ureido-4-quinolinamides, Bioorg. Med. Chem. 17 (2009) 203–221.pl
dc.description.referencesA.M. Gilbert, M.G. Bursavich, S. Lombardi, K.E. Georgiadis, E. Reifenberg, C. R. Flannery, E.A. Morris, N-((8-hydroxy-5-substituted-quinolin-7-yl)(phenyl) methyl)-2-phenyloxy/amino-acetamide inhibitors of ADAMTS-5 (Aggrecanase-2), Bioorg. Med. Chem. Lett. 18 (2008) 6454–6457.pl
dc.description.referencesR. Musiol, An overview of quinoline as a privileged scaffold in cancer drug discovery, Expert Opin. Drug Discov. 12 (2017) 583–597.pl
dc.description.referencesA. Budimir, Metal ions, Alzheimer’s disease and chelation therapy, Acta Pharm. 61 (2011) 1–14.pl
dc.description.referencesR.R. Crichton, D.T. Dexter, R.J. Ward, Metal based neurodegenerative diseases—From molecular mechanisms to therapeutic strategies, Coord. Chem. Rev. 252 (2008) 1189–1199.pl
dc.description.referencesL. Li, H. Wu, J. Wang, Z. Ji, T. Fang, H. Lu, L. Yan, F. Shen, D. Zhang, Y. Jiang, T. Ni, Discovery of Novel 8-Hydroxyquinoline Derivatives with Potent In Vitro and In Vivo Antifungal Activity, J. Med. Chem. 66 (2023) 16364–16376.pl
dc.description.referencesC. Bissani Gasparin, D.A. Pilger, 8-Hydroxyquinoline, Derivatives and MetalComplexes: A Review of Antileukemia Activities, ChemistrySelect 8 (2023) e202204219.pl
dc.description.referencesA. Barilli, C. Atzeri, I. Bassanetti, F. Ingoglia, V. Dall’Asta, O. Bussolati, M. Maffini, C. Mucchino, L. Marchio, Oxidative stress induced by copper and iron complexes with 8-hydroxyquinoline derivatives causes paraptotic death of HeLa cancer cells, Mol. Pharm. 11 (2014) 1151–1163.pl
dc.description.referencesX. Yang, P. Cai, Q. Liu, J. Wu, Y. Yin, X. Wang, L. Kong, Novel 8-hydroxyquinoline derivatives targeting beta-amyloid aggregation, metal chelation and oxidative stress against Alzheimer’s disease, Bioorg. Med. Chem. 26 (2018) 3191–3201.pl
dc.description.referencesR. Gupta, V. Luxami, K. Paul, Insights of 8-hydroxyquinolines: A novel target in medicinal chemistry, Bioorg. Chem. 108 (2021) 104633.pl
dc.description.referencesY.N. Song, H. Xu, W.M. Chen, P. Zhan, X.Y. Liu, 8-Hydroxyquinoline: a privileged structure with a broad-ranging pharmacological potential, Med. Chem. Comm. 6 (2015) 61–74.pl
dc.description.referencesS. Gama, M. Frontauria, N. Ueberschaar, G. Brancato, D. Milea, S. Sammartano, W. Plass, Thermodynamic study on 8-hydroxyquinoline-2-carboxylic acid as a chelating agent for iron found in the gut of Noctuid larvae, New J. Chem. 42 (2018) 8062–8073.pl
dc.description.referencesK. Arena, G. Brancato, F. Cacciola, F. Crea, S. Cataldo, C. De Stefano, S. Gama, G. Lando, D. Milea, L. Mondello, A. Pettignano, W. Plass, S. Sammartano, 8-Hydroxyquinoline-2-Carboxylic Acid as Possible Molybdophore: A MultiTechnique Approach to Define Its Chemical Speciation, Coordination and Sequestering Ability in Aqueous Solution, Biomolecules 10 (2020) 930.pl
dc.description.referencesA. Baryłka, A. Bagińska-Krakówka, L. Zuccarello, F. Mancuso, G. Gattuso, G. Lando,C. Sgarlata, C. De Stefano, B. Godlewska-Żyłkiewicz, D. Milea, S. Gama, Protonation equilibria of the tryptophan metabolite 8-hydroxyquinoline-2-carboxylic acid (8-HQA) and its precursors: A potentiometric and calorimetric comparative study, Thermochim. Acta 730 (2023) 179615.pl
dc.description.referencesŽ. Medoš, M. Bešter-Rogač, E. Leontidis, J. Tellinghuisen, Calibrating ITC instruments: Problems with weak base neutralization, Anal. Biochem. 694 (2024) 115602.pl
dc.description.referencesC. Sgarlata, V. Zito, G. Arena, Conditions for calibration of an isothermal titration calorimeter using chemical reactions, Anal. Bioanal. Chem. 405 (2013) 1085–1094.pl
dc.description.referencesC. De Stefano, S. Sammartano, P. Mineo, C. Rigano, Computer Tools for the Speciation of Natural Fluids, in: A. Gianguzza, E. Pelizzetti, S. Sammartano (Eds.), Marine Chemistry - an Environmental Analytical Chemistry Approach, Kluwer Academic Publishers, Amsterdam, 1997, pp. 71–83.pl
dc.description.referencesH.S. Harned, B.B. Owen, The physical chemistry of electrolytic solutions Reinhold Pub. Corp, Third edition ed., New York, 1958.pl
dc.description.referencesP. Gans, Hyperquad, http://www.hyperquad.co.uk/, Accessed: July 2024.pl
dc.description.referencesG. Arena, P. Gans, C. Sgarlata, HypCal, a general-purpose computer program for the determination of standard reaction enthalpy and binding constant values by means of calorimetry, Anal. Bioanal. Chem. 408 (2016) 6413–6422.pl
dc.description.referencesL. Castellino, E. Alladio, S. Bertinetti, G. Lando, C. De Stefano, S. Blasco, E. García-España , S. Gama, S. Berto, D. Milea, PyES – An open-source software for the computation of solution and precipitation equilibria, Chemom. Intell. Lab. Syst. 239 (2023) 104860.pl
dc.description.referencesA. Baryłka, B. Godlewska-Żyłkiewicz, D. Milea, S. Gama, The accurate assessment of the chemical speciation of complex systems through multi-technique approaches, Pure Appl. Chem. 96 (2024) 597–623.pl
dc.description.referencesG. Arena, C. Bretti, G.I. Grasso, G. Lando, S. Sammartano, C. Sgarlata, Thermodynamic study on levulinic acid in NaCl, (C2H5)4NI and mixed MgCl2/NaCl and CaCl2/NaCl aqueous solutions at T = 298.15 K, J. Chem. Thermodyn. 139 (2019) 105870.pl
dc.description.referencesC. Bretti, C. De Stefano, P. Cardiano, S. Cataldo, A. Pettignano, G. Arena, C. Sgarlata, G. Ida Grasso, G. Lando, S. Sammartano, Risedronate complexes with Mg2+, Zn2+, Pb2+, and Cu2+: Species thermodynamics and sequestering ability in NaCl(aq) at different ionic strengths and at T298.15 K, J. Mol. Liq. 343 (2021) 117699.pl
dc.description.referencesA. Albert, J.N. Phillips, 264. Ionization constants of heterocyclic substances. Part II. Hydroxy-derivatives of nitrogenous six-membered ring-compounds, J. Chem. Soc. (1956) 1294–1304.pl
dc.description.referencesG. Karpińska, A.P. Mazurek, J.C. Dobrowolski, Hydroxyquinolines: Constitutional isomers and tautomers, Comput. Theor. Chem. 972 (2011) 48-56.pl
dc.identifier.eissn1873-3166-
dc.description.volume417pl
dc.description.number126671pl
dc.description.firstpage1pl
dc.description.lastpage7pl
dc.identifier.citation2Journal of Molecular Liquidspl
dc.identifier.orcid0000-0002-4478-2919-
dc.identifier.orcid0009-0009-0584-5591-
dc.identifier.orcid0000-0003-4276-7384-
dc.identifier.orcid0000-0002-2576-4029-
dc.identifier.orcid0000-0002-9284-1303-
dc.identifier.orcid0000-0003-1188-8837-
dc.identifier.orcid0000-0002-9689-7435-
Występuje w kolekcji(ach):Artykuły naukowe (WChem)

Pliki w tej pozycji:
Plik Opis RozmiarFormat 
2025 Acid-base properties of HQ in aqueous solution JMolecular Liquids.pdf1,42 MBAdobe PDFOtwórz
Pokaż uproszczony widok rekordu Zobacz statystyki


Pozycja ta dostępna jest na podstawie licencji Licencja Creative Commons CCL Creative Commons