Calculation of Solubility of Oxyquinolinates
Affiliation(s)
Department of Oncology, The University Hospital in Cracow, Cracow, Poland. Faculty of Engineering and Chemical Technology, Technical University of Cracow, Cracow, Poland.
Department of Oncology, The University Hospital in Cracow, Cracow, Poland. Faculty of Engineering and Chemical Technology, Technical University of Cracow, Cracow, Poland.
ABSTRACT
The solubilities (s, mol/L) of different oxyquinolinates (oxinates, MeL2) are calculated using the formulae obtained according to elementary algebra, with the use of Excel spreadsheets. The calculations are involved with solution of algebraic equation of the third degree, obtained on the basis of concentration balances. The root of this equation, , is then inserted into the charge balance, and resolved according to zeroing procedure. In principle, the calculations are related to aqueous media. Nonetheless, the extension on liquid-liquid extraction systems is also proposed.
Cite this paper
Michałowska-Kaczmarczyk, A. and Michałowski, T. (2014) Calculation of Solubility of Oxyquinolinates. Journal of Analytical Sciences, Methods and Instrumentation, 4, 71-79. doi: 10.4236/jasmi.2014.43010.
Michałowska-Kaczmarczyk, A. and Michałowski, T. (2014) Calculation of Solubility of Oxyquinolinates. Journal of Analytical Sciences, Methods and Instrumentation, 4, 71-79. doi: 10.4236/jasmi.2014.43010.
References
[1] Albert, A. and Phillips, J.N. (1956) 264. Ionization Constants of Heterocyclic Substances. Part II. Hydroxy-Derivatives of Nitrogenous Six-Membered Ring-Compounds. Journal of the Chemical Society (Resumed), 1294-1304.
http://dx.doi.org/10.1039/jr9560001294 [2] Mills, D. (1978) 8-Hydroxyquinoline Inhibition of DNA Synthesis and Intragenic Recombination during Yeast Meiosis. Molecular and General Genetics, 162, 221-228. http://dx.doi.org/10.1007/BF00267879 [3] Philips, J.P. (1956) The Reactions of 8-Quinolinol, Chemical Reviews, 56, 271-297.
http://dx.doi.org/10.1021/cr50008a003 [4] Prachayasittikul, V., Prachayasittikul, S., Ruchirawat, S. and Prachayasittikul, V. (2013) 8-Hydroxyquinolines: A Review of Their Metal Chelating Properties and Medicinal Applications. Drug Design, Development and Therapy, 7, 1157-1178. http://dx.doi.org/10.2147/DDDT.S49763 [5] http://www.myhomeremedies.com/remedy.cgi?remedyid=7918 [6] Shen, A.Y., Wu, S.N. and Chiu, C.T. (1999) Synthesis and Cytotoxicity Evaluation of some 8-Hydroxyquinoline Derivatives. Journal of Pharmacy and Pharmacology, 51, 543-548.
http://dx.doi.org/10.1211/0022357991772826 [7] Oliveri, V., Giuffrida, M.L., Vecchio, G., Aiello, C. and Viale, M. (2012) Gluconjugates of 8-Hydroxyquinolines as Potential Anti-Cancer Prodrugs. Dalton Transactions, 41, 4530-4535.
http://dx.doi.org/10.1039/c2dt12371a [8] Halliwell, B. and Gutteridge, J.M. (1984) Oxygen Toxicity, Oxygen Radicals, Transition Metals and Disease. Biochemical Journal, 219, 1-14. [9] Crichton, R.R., Dexter, D.T. and Ward, R.J. (2011) Brain Iron Metabolism and Its Perturbation in Neurological Diseases. Journal of Neural Transmission, 118, 301-314. http://dx.doi.org/10.1007/s00702-010-0470-z [10] Halliwell, B. and Gutteridge, J.M. (1984) Oxygen Toxicity, Oxygen Radicals, Transition Metals and Disease. Biochemical Journal, 219, 1-14. [11] Valko, M., Morris, H. and Cronin, M.T. (2005) Metals, Toxicity and Oxidative Stress. Current Medicinal Chemistry, 12, 1161-1208. http://dx.doi.org/10.2174/0929867053764635 [12] Mau, J.L., Lin, H.C. and Song, S.F. (2002) Antioxidant Properties of Several Specialty Mushrooms. Food Research International, 35, 519-526. http://dx.doi.org/10.1016/S0963-9969(01)00150-8 [13] Gal, S., Fridkin, M., Amit, T., Zheng, H. and Youdim, M.B. (2006) M30, a Novel Multifunctional Neuroprotective Drug with Potent Iron Chelating and Brain Selective Monoamine Oxidase-ab Inhibitory Activity for Parkinson’s Disease. Journal of Neural Transmission, 70, 447-456.
http://link.springer.com/chapter/10.1007%2F978-3-211-45295-0_68#page-1 [14] Zheng, H., Weiner, L.M., Bar-Am, O., Epsztejn, M., Cabantchik, I., Warshawsky, A., Youdim, M.B.H. and Fridkin, M. (2005) Design, Synthesis, and Evaluation of Novel Bifunctional Iron-Chelators as Potential Agents for Neuroprotection in Alzheimer’s, Parkinson’s, and Other Neurodegenerative Diseases. Bioorganic & Medicinal Chemistry, 13, 773-783. http://dx.doi.org/10.1016/j.bmc.2004.10.037 [15] Mechlovich, D., Amit, T., Mandel, S.A., Bar-Am, O., Bloch, K., Vardi, P. and Youdim, M.B.H. (2010) The Novel Multifunctional, Iron-Chelating Drugs M30 and HLA20 Protect Pancreatic Beta-Cell Lines from Oxidative Stress Damage. Journal of Pharmacology and Experimental Therapeutics, 333, 874-882.
http://dx.doi.org/10.1124/jpet.109.164269 [16] Fernández-Bachiller, M.I., Pérez, C., González-Munoz, G.C., Conde, S., López, M.G., Villarroya, M., García, A.G. and Rodríguez-Franco, M.I. (2010) Novel Tacrine-8-Hydroxyquinoline Hybrids as Multifunctional Agents for the Treatment of Alzheimer’s Disease, with Neuroprotective, Cholinergic, Antioxidant, and Copper-Complexing Properties. Journal of Medicinal Chemistry, 53, 4927-4937. http://dx.doi.org/10.1021/jm100329q [17] Colak, A.T., Colak, F., Yesilel, O.Z. and Büyükgüngor, O. (2009) Synthesis, Spectroscopic, Thermal, Voltammetric Studies and Biological Activity of Crystalline Complexes of Pyridine-2,6-Dicarboxylic Acid and 8-Hydroxyquinoline. Journal of Molecular Structure, 936, 67-74. http://dx.doi.org/10.1016/j.molstruc.2009.07.026? [18] Albrecht, M., Fiege, M. and Osetska, O. (2008) 8-Hydroxyquinolines in Metallosupramolecular Chemistry. Coordination Chemistry Reviews, 252, 812-824. http://dx.doi.org/10.1016/j.ccr.2007.06.003 [19] Nicoletti, G., Domalewska, E. and Borland, R. (1999) Fungitoxicity of Oxine and Copper Oxinate: Effects of pH, Metals and Chelating Agents on Activity. Mycological Research, 103, 1085-1097.
http://dx.doi.org/10.1017/S0953756298008247 [20] Budimir, A. (2011) Metal Ions, Alzheimer’s Disease and Chelation Therapy. Acta Pharmaceutica, 61, 1-14.
http://dx.doi.org/10.2478/v10007-011-0006-6 [21] Crichton, R.R., Dexter, D.T. and Ward, R.J. (2008) Metal Based Neurodegenerative Diseases—From Molecular Mechanisms to Therapeutic Strategies. Coordination Chemistry Reviews, 252, 1189-1199.
http://dx.doi.org/10.1016/j.ccr.2007.10.019 [22] Vanparia, S.F., Patel, T.S., Sojitra, N.A., Jagani, C.L., Dixit, B.C., Patel, P.S. and Dixit, R.B. (2010) Synthesis, Characterization and Antimicrobial Study of Novel 4-{[(8-Hydroxyquinolin-5-yl)Methyl]Amino}Benzenesulfonamide and Its Oxinates. Acta Chimica Slovenica, 57, 660-667. [23] Katakura, R. and Koide, Y. (2006) Configuration-Specific Synthesis of the Facial and Meridional Isomers of Tris(8-Hydroxyquinolinate) Aluminum(Alq3). Inorganic Chemistry, 45, 5730-5732.
http://dx.doi.org/10.1021/ic060594s [24] Montes, V.A., Pohl, R., Shinar, J. and Anzenbacher Jr., P. (2006) Effective Manipulation of the Electronic Effects and Its Influence on the Emission of 5-Substituted Tris(8-Quinolinolate) Aluminum(III) Complexes. Chemistry—A European Journal, 12, 4523-4535. http://dx.doi.org/10.1002/chem.200501403 [25] Sugawara, K.F., Weetall, H.H. and Schucker, G.D. (1974) Preparation, Properties, and Applications of 8-Hydroxyquinoline Immobilized Chelate. Analytical Chemistry, 46, 489-492.
http://dx.doi.org/10.1021/ac60340a016 [26] Pedersen, O. (2006) Pharmaceutical Chemical Analysis: Methods for Identification and Limit Tests. CRC Taylor & Francis, Boca Raton. http://dx.doi.org/10.1201/9780203492260 [27] Ryabchenko, E.V., Yanovskaya, E.S., Tertykh, V.A. and Kichkiruk, O.Y. (2013) Complexation of Transition Metals with 8-Hydroxyquinoline Chemically Immobilized on the Surface. Russian Journal of Inorganic Chemistry, 58, 361-366. http://dx.doi.org/10.1134/S0036023613030145 [28] Inczédy, J. (1976) Analytical Applications of Complex Equilibria. Wiley, New York. [29] Ju. Lurie (1975) Handbook of Analytical Chemistry. Mir Publishers, Moscow. [30] Ringbom, A. (1963) Complexation in Analytical Chemistry. Interscience, New York. [31] Kotrly, S. and Sucha, L. (1985) Handbook of Chemical Equilibria in Analytical Chemistry (Ellis Horwood Series in Analytical Chemistry). Ellis Horwood Ltd.
http://www.amazon.com/Handbook-Chemical-Equilibria-Analytical-Chemistry/dp/0133819892/ref=dp_ob_title_bk [32] http://en.wikipedia.org/wiki/Cubic_function [33] Minczewski, J., Chwastowska, J., Dybczyński, R. and Masson, M.R. (1982) Separation and Preconcentration Methods in Inorganic Trace Analysis. E. Horwood, Chichester, Halsted Press, New York.
http://trove.nla.gov.au/work/25176914?q=+&versionId=30353525 [34] Janecki, D., Doktór, K. and Michalowski, T. (1999) Determination of Stability Constants of Complexes of MiKjHkL Type in Concentrated Solutions of Mixed Salts. Talanta, 48, 1191-1197. [35] Janecki, D., Styszko-Grochowiak, K. and Michalowski, T. (2000) The Catenation and Isomerisation Effects on Stability Constants of Complexes Formed by Some Diprotic Acids. Talanta, 52, 555-562.
http://dx.doi.org/10.1016/S0039-9140(00)00361-1 [36] Michalowski, T., Baterowicz, A. and Wójtowicz, A. (2000) Sources of Error in β-Correction Spectrophotometry. Talanta, 52, 337-340. http://dx.doi.org/10.1016/S0039-9140(00)00299-X? [37] Michalowski, T. and Pietrzyk, A. (2006) A Thermodynamic Study of Struvite + Water System. Talanta, 68, 594-601.
http://dx.doi.org/10.1016/j.talanta.2005.04.052 [38] Michalowski, T. and Asuero, A.G. (2012) Thermodynamic Modelling of Dolomite Behavior in Aqueous Media. Journal of Thermodynamics, 2012, Article ID: 723052, 12 pages. http://www.hindawi.com/journals/jtd/2012/723052/cta/
http://dx.doi.org/10.1155/2012/723052 [39] Michalowski, T. (2011) Application of GATES and MATLAB for Resolution of Equilibrium, Metastable and Non-Equilibrium Electrolytic Systems, Chapter 1. In: Micha?owski, T., Ed., Applications of MATLAB in Science and Engineering, InTech-Open Access Publisher in the Fields of Science, Technology and Medicine, 1-34.
http://www.intechopen.com/books/show/title/applications-of-matlab-in-science-and-engineering
[1] Albert, A. and Phillips, J.N. (1956) 264. Ionization Constants of Heterocyclic Substances. Part II. Hydroxy-Derivatives of Nitrogenous Six-Membered Ring-Compounds. Journal of the Chemical Society (Resumed), 1294-1304.
http://dx.doi.org/10.1039/jr9560001294 [2] Mills, D. (1978) 8-Hydroxyquinoline Inhibition of DNA Synthesis and Intragenic Recombination during Yeast Meiosis. Molecular and General Genetics, 162, 221-228. http://dx.doi.org/10.1007/BF00267879 [3] Philips, J.P. (1956) The Reactions of 8-Quinolinol, Chemical Reviews, 56, 271-297.
http://dx.doi.org/10.1021/cr50008a003 [4] Prachayasittikul, V., Prachayasittikul, S., Ruchirawat, S. and Prachayasittikul, V. (2013) 8-Hydroxyquinolines: A Review of Their Metal Chelating Properties and Medicinal Applications. Drug Design, Development and Therapy, 7, 1157-1178. http://dx.doi.org/10.2147/DDDT.S49763 [5] http://www.myhomeremedies.com/remedy.cgi?remedyid=7918 [6] Shen, A.Y., Wu, S.N. and Chiu, C.T. (1999) Synthesis and Cytotoxicity Evaluation of some 8-Hydroxyquinoline Derivatives. Journal of Pharmacy and Pharmacology, 51, 543-548.
http://dx.doi.org/10.1211/0022357991772826 [7] Oliveri, V., Giuffrida, M.L., Vecchio, G., Aiello, C. and Viale, M. (2012) Gluconjugates of 8-Hydroxyquinolines as Potential Anti-Cancer Prodrugs. Dalton Transactions, 41, 4530-4535.
http://dx.doi.org/10.1039/c2dt12371a [8] Halliwell, B. and Gutteridge, J.M. (1984) Oxygen Toxicity, Oxygen Radicals, Transition Metals and Disease. Biochemical Journal, 219, 1-14. [9] Crichton, R.R., Dexter, D.T. and Ward, R.J. (2011) Brain Iron Metabolism and Its Perturbation in Neurological Diseases. Journal of Neural Transmission, 118, 301-314. http://dx.doi.org/10.1007/s00702-010-0470-z [10] Halliwell, B. and Gutteridge, J.M. (1984) Oxygen Toxicity, Oxygen Radicals, Transition Metals and Disease. Biochemical Journal, 219, 1-14. [11] Valko, M., Morris, H. and Cronin, M.T. (2005) Metals, Toxicity and Oxidative Stress. Current Medicinal Chemistry, 12, 1161-1208. http://dx.doi.org/10.2174/0929867053764635 [12] Mau, J.L., Lin, H.C. and Song, S.F. (2002) Antioxidant Properties of Several Specialty Mushrooms. Food Research International, 35, 519-526. http://dx.doi.org/10.1016/S0963-9969(01)00150-8 [13] Gal, S., Fridkin, M., Amit, T., Zheng, H. and Youdim, M.B. (2006) M30, a Novel Multifunctional Neuroprotective Drug with Potent Iron Chelating and Brain Selective Monoamine Oxidase-ab Inhibitory Activity for Parkinson’s Disease. Journal of Neural Transmission, 70, 447-456.
http://link.springer.com/chapter/10.1007%2F978-3-211-45295-0_68#page-1 [14] Zheng, H., Weiner, L.M., Bar-Am, O., Epsztejn, M., Cabantchik, I., Warshawsky, A., Youdim, M.B.H. and Fridkin, M. (2005) Design, Synthesis, and Evaluation of Novel Bifunctional Iron-Chelators as Potential Agents for Neuroprotection in Alzheimer’s, Parkinson’s, and Other Neurodegenerative Diseases. Bioorganic & Medicinal Chemistry, 13, 773-783. http://dx.doi.org/10.1016/j.bmc.2004.10.037 [15] Mechlovich, D., Amit, T., Mandel, S.A., Bar-Am, O., Bloch, K., Vardi, P. and Youdim, M.B.H. (2010) The Novel Multifunctional, Iron-Chelating Drugs M30 and HLA20 Protect Pancreatic Beta-Cell Lines from Oxidative Stress Damage. Journal of Pharmacology and Experimental Therapeutics, 333, 874-882.
http://dx.doi.org/10.1124/jpet.109.164269 [16] Fernández-Bachiller, M.I., Pérez, C., González-Munoz, G.C., Conde, S., López, M.G., Villarroya, M., García, A.G. and Rodríguez-Franco, M.I. (2010) Novel Tacrine-8-Hydroxyquinoline Hybrids as Multifunctional Agents for the Treatment of Alzheimer’s Disease, with Neuroprotective, Cholinergic, Antioxidant, and Copper-Complexing Properties. Journal of Medicinal Chemistry, 53, 4927-4937. http://dx.doi.org/10.1021/jm100329q [17] Colak, A.T., Colak, F., Yesilel, O.Z. and Büyükgüngor, O. (2009) Synthesis, Spectroscopic, Thermal, Voltammetric Studies and Biological Activity of Crystalline Complexes of Pyridine-2,6-Dicarboxylic Acid and 8-Hydroxyquinoline. Journal of Molecular Structure, 936, 67-74. http://dx.doi.org/10.1016/j.molstruc.2009.07.026? [18] Albrecht, M., Fiege, M. and Osetska, O. (2008) 8-Hydroxyquinolines in Metallosupramolecular Chemistry. Coordination Chemistry Reviews, 252, 812-824. http://dx.doi.org/10.1016/j.ccr.2007.06.003 [19] Nicoletti, G., Domalewska, E. and Borland, R. (1999) Fungitoxicity of Oxine and Copper Oxinate: Effects of pH, Metals and Chelating Agents on Activity. Mycological Research, 103, 1085-1097.
http://dx.doi.org/10.1017/S0953756298008247 [20] Budimir, A. (2011) Metal Ions, Alzheimer’s Disease and Chelation Therapy. Acta Pharmaceutica, 61, 1-14.
http://dx.doi.org/10.2478/v10007-011-0006-6 [21] Crichton, R.R., Dexter, D.T. and Ward, R.J. (2008) Metal Based Neurodegenerative Diseases—From Molecular Mechanisms to Therapeutic Strategies. Coordination Chemistry Reviews, 252, 1189-1199.
http://dx.doi.org/10.1016/j.ccr.2007.10.019 [22] Vanparia, S.F., Patel, T.S., Sojitra, N.A., Jagani, C.L., Dixit, B.C., Patel, P.S. and Dixit, R.B. (2010) Synthesis, Characterization and Antimicrobial Study of Novel 4-{[(8-Hydroxyquinolin-5-yl)Methyl]Amino}Benzenesulfonamide and Its Oxinates. Acta Chimica Slovenica, 57, 660-667. [23] Katakura, R. and Koide, Y. (2006) Configuration-Specific Synthesis of the Facial and Meridional Isomers of Tris(8-Hydroxyquinolinate) Aluminum(Alq3). Inorganic Chemistry, 45, 5730-5732.
http://dx.doi.org/10.1021/ic060594s [24] Montes, V.A., Pohl, R., Shinar, J. and Anzenbacher Jr., P. (2006) Effective Manipulation of the Electronic Effects and Its Influence on the Emission of 5-Substituted Tris(8-Quinolinolate) Aluminum(III) Complexes. Chemistry—A European Journal, 12, 4523-4535. http://dx.doi.org/10.1002/chem.200501403 [25] Sugawara, K.F., Weetall, H.H. and Schucker, G.D. (1974) Preparation, Properties, and Applications of 8-Hydroxyquinoline Immobilized Chelate. Analytical Chemistry, 46, 489-492.
http://dx.doi.org/10.1021/ac60340a016 [26] Pedersen, O. (2006) Pharmaceutical Chemical Analysis: Methods for Identification and Limit Tests. CRC Taylor & Francis, Boca Raton. http://dx.doi.org/10.1201/9780203492260 [27] Ryabchenko, E.V., Yanovskaya, E.S., Tertykh, V.A. and Kichkiruk, O.Y. (2013) Complexation of Transition Metals with 8-Hydroxyquinoline Chemically Immobilized on the Surface. Russian Journal of Inorganic Chemistry, 58, 361-366. http://dx.doi.org/10.1134/S0036023613030145 [28] Inczédy, J. (1976) Analytical Applications of Complex Equilibria. Wiley, New York. [29] Ju. Lurie (1975) Handbook of Analytical Chemistry. Mir Publishers, Moscow. [30] Ringbom, A. (1963) Complexation in Analytical Chemistry. Interscience, New York. [31] Kotrly, S. and Sucha, L. (1985) Handbook of Chemical Equilibria in Analytical Chemistry (Ellis Horwood Series in Analytical Chemistry). Ellis Horwood Ltd.
http://www.amazon.com/Handbook-Chemical-Equilibria-Analytical-Chemistry/dp/0133819892/ref=dp_ob_title_bk [32] http://en.wikipedia.org/wiki/Cubic_function [33] Minczewski, J., Chwastowska, J., Dybczyński, R. and Masson, M.R. (1982) Separation and Preconcentration Methods in Inorganic Trace Analysis. E. Horwood, Chichester, Halsted Press, New York.
http://trove.nla.gov.au/work/25176914?q=+&versionId=30353525 [34] Janecki, D., Doktór, K. and Michalowski, T. (1999) Determination of Stability Constants of Complexes of MiKjHkL Type in Concentrated Solutions of Mixed Salts. Talanta, 48, 1191-1197. [35] Janecki, D., Styszko-Grochowiak, K. and Michalowski, T. (2000) The Catenation and Isomerisation Effects on Stability Constants of Complexes Formed by Some Diprotic Acids. Talanta, 52, 555-562.
http://dx.doi.org/10.1016/S0039-9140(00)00361-1 [36] Michalowski, T., Baterowicz, A. and Wójtowicz, A. (2000) Sources of Error in β-Correction Spectrophotometry. Talanta, 52, 337-340. http://dx.doi.org/10.1016/S0039-9140(00)00299-X? [37] Michalowski, T. and Pietrzyk, A. (2006) A Thermodynamic Study of Struvite + Water System. Talanta, 68, 594-601.
http://dx.doi.org/10.1016/j.talanta.2005.04.052 [38] Michalowski, T. and Asuero, A.G. (2012) Thermodynamic Modelling of Dolomite Behavior in Aqueous Media. Journal of Thermodynamics, 2012, Article ID: 723052, 12 pages. http://www.hindawi.com/journals/jtd/2012/723052/cta/
http://dx.doi.org/10.1155/2012/723052 [39] Michalowski, T. (2011) Application of GATES and MATLAB for Resolution of Equilibrium, Metastable and Non-Equilibrium Electrolytic Systems, Chapter 1. In: Micha?owski, T., Ed., Applications of MATLAB in Science and Engineering, InTech-Open Access Publisher in the Fields of Science, Technology and Medicine, 1-34.
http://www.intechopen.com/books/show/title/applications-of-matlab-in-science-and-engineering