Theoretical insights on the relationship between detection limit and complex stability of oxine ligand

Yıl 2024, Cilt: 8 Sayı: 1, 65 - 79, 15.01.2024

Boulanouar Messaoudı Naceur Benhadrıa Tarik Attar

https://doi.org/10.33435/tcandtc.1252038

Öz

The concept of detection limit was combined with quantum chemical calculations for trace analysis of cadmium and lead in aqueous solution using deprotonated 8-hydroxyquinoline (oxine) as ligand. The DFT study was performed using 6-31G(d), cc-pVTZ and SDD basis sets in combination with different theoretical methods such as; B3LYP, MP2 and M06L implemented in Gaussian 09 program package. The obtained results of the study in the gas and aqueous phases show that the chemical stability of the complex was found in the order Pb-oxine > Cd-oxine. Based on the calculations done, the stability order was relative to the detection limit (LOD) for the two metals Cd and Pb. Thus, a reverse relationship between LOD and binding energy has been found.

Anahtar Kelimeler

Cadmium, Lead, Oxine, Binding energy, DFT.

Kaynakça

• [1] T. Attar, “A mini-review on importance and role of trace elements in the human organism,” Chemical Review Letters, 3 (2020) 117-130.
• [2] T. Attar, Y. Harek, N. Dennouni-Medjati, et al., “Dosage du cadmium et du plomb dans le sang humain par voltamétrie à redissolutionanodique,” Annales de Biologie Clinique, 70 (2012) 595-8.
• [3] G. Flora, D. Gupta, A. Tiwari, “Toxicity of lead: a review with recent updates,” Interdisciplinary Toxicology, 5 (2012) 47-58.
• [4] T. Attar, “Levels of serum copper and zinc in healthy adults from the west of Algeria,” SPC Journal of Environmental Sciences, 1 (2019) 26-28.
• [5] C.C. Bridges, R.K. Zalups, “Molecular and ionic mimicry and the transport of toxic metals,” Toxicology and Applied Pharmacology, 204 (2005) 274-308.
• [6] D. Mohan, K.P. Singh, “Single- and multi-component adsorption of cadmium and zinc using activated carbon derived from bagasse-an agricultural waste,” Water Research, 36 (2020) 2304-2318.
• [7] T. Attar, Y. Harek, N. Dennouni-Medjati, et al., “Determination of zinc levels in healthy adults from the west of Algeria by differential pulse anodic stripping voltammetry,” Journal: Journal of Advances in Chemistry, 6 (2013) 855-860.
• [8] M. Serge, B.R. Karanga Yssouf, T. Issa, et al., “Electrochemical determination of diuron in soil using a nanocrystalline cellulose modified carbon paste electrode,” International Journal of Electrochemical Science, 16 (2021) 1-15.
• [9] N. Thị Hue, N. Van Hop, H. Thai Long, et al., “Determination of chromium in natural water by adsorptive stripping voltammetry using in situ bismuth film electrode,” Journal of Environmental and Public Health, 2020 (2020) 1-10.
• [10] H. Evard, A. Kruve, I. Leito, “Tutorial on estimating the limit of detection using LC-MS analysis, part II: Practical aspects,” Analytica Chimica Acta, 942 (2016) 40-49.
• [11] T. Attar, Y. Harek, L. Lahcen, “Determination of ultra trace levels of copper in whole blood by adsorptive stripping voltammetry,” Korean Chemical Society, 57 (2013) 568-573.
• [12] T. Attar, Y. Harek, L. Lahcen, “Determination of copper in whole blood by differential pulse adsorptive stripping voltammetry,” Mediterranean Journal of Chemistry, 2 (2014) 691-700.
• [13] I.H. Taşdemir, M.A. Akay, N. Erk, “Voltammetric behavior of telmisartan and cathodic adsorptive stripping voltammetric method for its assay in pharmaceutical dosage forms and biological fluids,” Electroanalysis, 22 (2010) 2101-2109.
• [14] P. Leanderson, C. Tagesson, “Iron bound to the lipophilic iron chelator, 8-hydroxyquinoline, causes DNA strand breakage in cultured lung cells” Carcinogenesis, 17 (1996) 545-550.
• [15] G. Lescoat, S. Léonce, A. Pierré, et al.,“Antiproliferative and iron chelating efficiency of the new bis-8-hydroxyquinoline benzylaminechelator S1 in hepatocyte cultures,” Chemico-biological interactions, 195 (2012) 165-172.
• [16] R.B. Dixit, T.S. Patel, S.F. Vanparia, et al.,“DNA-binding interaction studies of microwave assisted synthesized sulfonamide substituted 8-hydroxyquinoline derivatives,” Scientia pharmaceutica, 79 (2011) 293-308.
• [17] W.Q. Ding, B. Liu, J.L. Vaught, et al., “Anticancer activity of the antibiotic clioquinol,” Cancer Research, 65 (2005) 3389-3395.
• [18] S. Prachayasittikul, A. Worachartcheewan, R. Pingaew, et al., “Metal complexes of uracil derivatives with cytotoxicity and superoxide scavenging activity,” Letters in Drug Design & Discovery, 9 (2012) 282-287.
• [19] Y. Anjaneyulu, R.P. Rao, R.Y. Swamy, et al.,“In vitro antimicrobial-activity studies on the mixed ligand complexes of Hg(II) with 8-hydroxyquinoline and salicylic acids,” Proceedings of the Indian Academy of Sciences-Chemical Sciences, 91 (1982) 157-163.
• [20] C.M. Van Den Berg, “Determination of copper, cadmium and lead in seawater by cathodic stripping voltammetry of complexes with 8-hydroxyquinoline,” Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, 215 (1986) 111-121.
• [21] H. Darougari, M. Rezaei-Sameti, “The drug delivery appraisal of Cu and Ni decorated B12N12 nanocage for an 8-hydroxyquinoline drug: A DFT and TD-DFT computational study,” Asian Journal of Nanoscience and Materials, 5 (2022) 196-210.
• [22] A. Cipurković, E. Horozić, S. Marić, et al., “Metal complexes with 8-hydroxyquinoline: synthesis and in vitro antimicrobial activity,” Open Journal of Applied Sciences, 11 (2021) 1-10.
• [23] V.V.N. Ravi Kishore, A. Aziz, K.L. Narasimhan, et al., “On the assignment of the absorption bands in the optical spectrum of Alq3,” Synthetic Metals, 126 (2002) 199-205.
• [24] R. Rahier, A. Noiriel, A. Abousalham, “Development of a direct and continuous phospholipase D assay based on the chelation-enhanced fluorescence property of 8-hydroxyquinoline,” Analytical chemistry, 88 (2016) 666-674.
• [25] J. Murgich, H.J. Franco, “A Density functional theory study of the topology of the charge density of complexes of 8-hydroxyquinoline with Mn(III), Fe(III), and Co(III),” The Journal of Physical Chemistry A, 113 (2009) 5205-5211.
• [26] M. Amati, S. Belviso, P.L. Cristinziano, et al., “8-hydroxyquinoline monomer, water adducts, and dimer. Environmental influences on structure, spectroscopic properties, and relative stability of cis and trans conformers,” The Journal of Physical Chemistry A, 111 (2007) 13403-13414.
• [27] N. Benhadria, T. Attar, B. Messaoudi, “Understanding the link between the detection limit and the energy stability of two quercetin–antimony complexes by means of conceptual DFT,” South African Journal of Chemistry, 73 (2020) 120-124.
• [28] T. Attar, B. Messaoudi, N. Benhadria, “DFT theoretical study of some thiosemicarbazide derivatives with copper,” Chemistry & Chemical Technology, 14 (2020) 20-25.
• [29] N. Benhadria, B. Messaoudi, T. Attar, “The study of the correlation between the detection limit and the energy stability of two antimony complexes by means of conceptual DFT,” Malaysian Journal of Chemistry, 22 (2020) 111-120.
• [30] B. Messaoudi, T. Attar, N. Benhadria, “DFT study of some copper complexes and their detection limits,” Chemistry and Chemical Technology, 16 (2022) 185-194.
• [31] A. Cipurković, E. Horozić, S. Marić, et al., “Metal complexes with 8-hydroxyquinoline: synthesis and in vitro antimicrobial activity,” Open Journal of Applied Sciences, 11 (2021) 1-10.
• [32] AD. Becke, “Density-functional thermochemistry. III. The role of exact exchange,” The Journal of Chemical Physics, 98 (1993) 5648-5652.
• [33] L. Domingo, M. Aurell, P. Perez, et al., “Quantitative characterization of the global electrophilicity power of common diene/dienophile pairs in Diels–Alder reactions,” Tetrahedron, 58 (2002) 4417-4423.
• [34] J. Tomasi, B. Mennucci, E. Cancès, “The IEF version of the PCM solvation method: An overview of a new method addressed to study molecular solutes at the QM ab initio level,” Journal of Moecular Structure (Theochem), 464 (1999) 211-226.
• [35] M. Cossi, N. Rega, G. Scalmani, et al., “Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model,” Journal of Computational Chemistry, 24 (2003) 669-681.
• [36] J. Tomasi, B. Mennucci, R. Cammi, “Quantum mechanical continuum solvation models,” Chemical Review, 105 (2005) 2999-3093.
• [37] S. Pokharia, R. Joshi, M. Pokharia, et al., “A density functional theory insight into the structure and reactivity of diphenyltin(IV) derivative of glycylphenylalanine,” Main Group Metal Chemistry, 39 (2016) 77-86.
• [38] K.A. Moltved, K.P. Kepp, “Using electronegativity and hardness to test density functional,” Chemical Physics, 152 (2020) 1-12.
• [39] R.G. Parr, L.V. Szentpaly, S. Liu, “Electrophilicity index,” Journal of American Chemical Society, 121 (1999) 1922-1924.
• [40] A. Benchadli, T. Attar, B. Messaoudi, et al., “Polyvinylpyrrolidone as a corrosion inhibitor for carbon steel in a perchloric acid solution: effect of structural size,” Hungarian Journal of Industry and Chemistry, 49 (2021) 59-69.
• [41] T. Attar, A. Benchadli, B. Messaoudi, et al., “Experimental and theoretical studies of eosin Y dye as corrosion inhibitors for carbon steel in perchloric acid solution,” Bulletin of Chemical Reaction Engineering & Catalysis, 15 (2020) 454-464.
• [42] T. Attar, F. Nouali, Z. Kibou, et al., “Corrosion inhibition, adsorption and thermodynamic properties of 2-aminopyridine derivatives on the corrosion of carbon steel in sulfuric acid solution,” Journal of Chemical Sciences, 133 (2021) 109-119.
• [43] M. Abreu-Quijano, M. Palomar-Pardavé, A. Cuan, “Quantum chemical study of 2-mercaptoimidazole, 2-mercaptobenzimidazole, 2-mercapto-5-methylbenzimidazole and 2-mercapto-5-nitrobenzimidazole as corrosion inhibitors for steel,” International Journal of Electrochemical Sciences, 6 (2011) 3729-3742.
• [44] H.T. He, X. Lecai, Z. Jingsen, et al., “Binding characteristics of Cd2+, Zn2+, Cu2+ and Li+ with humic substances: implication to trace element enrichment in low-rank coals,” Energy Exploration & Exploitation, 34 (2016) 735-745.
• [45] T. Sakajiri, H. Yajima, T. Yamamura, “Density functional theory study on metal-binding energies for human serum transferrin-metal complexes,” International Scholarly Research Notices, 2012 (2012) 1-5.
• [46] H. Hata, D. Phuoc Tran, M. Marzouk Sobeh, et al., “Binding free energy of protein/ligand complexes calculated using dissociation parallel cascade selection molecular dynamics and Markov state model,” Biophys Physicobiology, 18 (2021) 305-316.
• [47] J. Aihara, “Reduced HOMO−LUMO gap as an index of kinetic stability for polycyclic aromatic hydrocarbons,” Journal of Physical Chemistry A, 103 (1999) 7487-7495.
• [48] D.E. Manolopoulos, J.C. May, S.E. Down, “Theoretical studies of the fullerenes: C34 to C70,” Chemical Physics Letters, 181 (1991) 105-111.
• [49] Y. Ruiz-Morales, “HOMO−LUMO gap as an index of molecular size and structure for polycyclic aromatic hydrocarbons (PAHS) and asphaltenes:  a theoretical study,”Journal of Physical Chemistry A, 106 (2002) 11283-11308.
• [50] A. Asghar, M.M. Bello, A.A.A. Raman, et al., “Predicting the degradation potential of Aacid blue 113 by different oxidants using quantum chemical analysis,” Heliyon, 5 (2019) e02396.
• [51] M. Dudev, J. Wang, T. Dudev, et al., “Factors governing the metal coordination number in metal complexes from cambridge structural database analyses,” The Journal of Physical Chemistry B, 110 (2006) 1889-1895.
• [52] G. Kuppuraj, M. Dudev, C. Lim, “Factors governing metal−ligand distances and coordination geometries of metal complexes,” The Journal of Physical Chemistry B, 113 (2009) 2952-2960.
• [53] N.M. Thanh, N.D. Luyen, T. Thanh Tam Toan, et al., “Voltammetry determination of Pb(II), Cd(II), and Zn(II) at bismuth film electrode combined with 8-hydroxyquinoline as a complexing agent,” Journal of Analytical Methods in Chemistry, 2019 (2019) 1-11.
• [54] T. Yamamura, K. Ichimura, T. Tsuda, et al., “Lanthanoid complex of iron-transport protein, transferring-kinetic-study on release of the metal from N-binding and C-binding sites,” Nippon Kagaku Kaishi, 4 (1988) 452-458.
• [55] R.D. Shannon, “Revised effective ionic radii and systematic studies of interatomic distances in halides and chalcogenides,” Acta crystallographica section A: crystal physics, diffraction, theoretical and general crystallography, 32 (1976) 751-767.
• [56] T. Rakitskaya, A. Truba, E. Radchenko, et al., “Mono- and bimetallic complexes of Mn(II), Co(II), Cu(II), and Zn(II) with schiff bases immobilized on nanosilica as catalysts in ozone decomposition reaction,” Chemistry and Chemical Technology, 12 (2018) 1-6.