Effect of Ligand Structures for Determination of Histidine Using Dinuclear Copper (II) Complexes with Anthracene Derivative Ligands by Indicator Displacement Assay Approach
Abstract
The formation of the ensembles between dinuclear copper (II) complexes of anthracene derivative ligands, Cu2L1 and Cu2L2, with fluorescence indicator Eosin Y was studied, aiming to employ the ensembles to detect histidine (His) by using an indicator displacement assay approach (IDAs). Experiments were carried out in 80/20 (%v/v) MeCN/H2O in the presence of 0.01 M HEPES buffer at pH 7.4. The ensemble formation constants (log K) of Cu2L1 and Cu2L2 with Eosin Y were calculated to be 3.82 ± 0.25 and 4.91 ± 0.33, respectively. Interestingly, it was found that only Cu2L2 ensemble could detect His selectively, whereas the Cu2L1 ensemble could respond to other amino acids. Thus, Cu2L2 can be used as a receptor to determine His with fluorescence indicator Eosin Y as a signaling unit under an indicator displacement assay approach. Keywords : dinuclear copper (II) complexes, indicator displacement assay, anthracene derivative ligands, histidine amino acid, fluorescence sensorReferences
Binstead, R. A., Jung, B., Zuberbühler, A. D., SPECFIT/32 Global analysis System, 3.0, Spectrum Software Associates, Marlborough, MA, 2000.
Bolinl, M., Akerud, P., Hansson, A., & Akerud, H., (2011). Histidine-Rich Glycoprotein as an Early Biomarker of Preeclampsia. American Journal of Hypertension, 24, 496-501.
Folmer-Andersen, J. F., Lynch, V. M. Anslyn, E. V. (2005). “Naked-Eye” Detection of Histidine by Regulation of Cu(II) Coordination Modes. Chemistry - A European Journal, 11, 5319–5326.
Incarvito, C., Lam, M., Rhatigan, B., Rheingold, A. L., Qin, C. J., Gavrilova, A. L., Bosnich, B. (2001). Bimetallic Reactivity. Preparations, Properties and Structures of Complexes Formed by Unsymmetrical Binucleating Ligands Bearing 4- and 6-Coordinate Sites Supported by Alkoxide Bridges. Journal of the Chemical Society, Dalton Transactions, 23, 3478-3488.
Kaspar, H., Dettmer, K., Gronwald, W., and Oefner P.J. (2008). Automated GC–MS Analysis of Free Amino Acids in Biological Fluids. Journal of Chromatography B, 870, 222-232.
Kovach, P. M., Meyerhoff, M. E. (1982). Development and Application of a Histidine-Selective Biomembrane Electrode. Analytical Chemistry. 54(2), 217-220.
Liu, Z., Yang, Z., Li, T., Wang, B., Li, Y., Qin, D. Wang, M. Yana, M. (2011). An Effective Cu(II) Quenching Fluorescence Sensor in Aqueous Solution and 1D Chain Coordination Polymer Framework. Dalton Transactions, 40, 9370-9373.
Nan, C. G., Ping, W. X., Ping, D. J., Qing, C. H. (1999). A Study on Electrochemistry of Histidine and Its Metabolites based on the Diazo Coupling Reaction. Talanta, 49, 319-330.
Sulliva Jr, D. J., Gluzman, I. Y., Goldberg, D. E. (1996). Plasmodium Hemozoin Formation Mediated by Histidine-Rich Proteins. Science, 271, 219-222.
Tang, F., Wu, K. K., Nie, Z., Ding, L., Liu, Q., Yuan, J., Guo, M., Yao, S. (2008). Quantification of Amino Acid Ionic Liquids Using Liquid Chromatography–Mass Spectrometry. Journal of Chromatography A, 1208, 175-181.
Wada, H.& Fernando, Q.(1971).Determination of Formation Constants of Copper(II)Complexes of (Hydroxyethylidene)diphosphonic Acid with Solid State Cupric Ion-Selective Electrode. Analytical Chemistry, 43(6), 751–755.
Watchasit, S., Suktanarak, P., Suksai, C., Ruangpornvisuti, V., Tuntulani, T. (2014). Discriminate Sensing of Pyrophosphate Using a New Tripodal Tetramine-Based Dinuclear Zn(II) Complex Under an Indicator Displacement Assay Approach. Dalton Transactions, 43, 14701-14709.
Wiskur, S.L., Ait-Haddou, H., Lavigne, J.J., Anslyn, E.V. (2001). Teaching Old Indicators New Tricks. Accounts of Chemical Research, 34(12), 963-972.
Zhang, J., Sun L., Yoshida T. (2011). Spectroelectrochemical Studies on Redox Reactions of Eosin Y and Its Polymerization with Zn2+ Ions. Journal of Electroanalytical Chemistry, 662, 384-395.
Bolinl, M., Akerud, P., Hansson, A., & Akerud, H., (2011). Histidine-Rich Glycoprotein as an Early Biomarker of Preeclampsia. American Journal of Hypertension, 24, 496-501.
Folmer-Andersen, J. F., Lynch, V. M. Anslyn, E. V. (2005). “Naked-Eye” Detection of Histidine by Regulation of Cu(II) Coordination Modes. Chemistry - A European Journal, 11, 5319–5326.
Incarvito, C., Lam, M., Rhatigan, B., Rheingold, A. L., Qin, C. J., Gavrilova, A. L., Bosnich, B. (2001). Bimetallic Reactivity. Preparations, Properties and Structures of Complexes Formed by Unsymmetrical Binucleating Ligands Bearing 4- and 6-Coordinate Sites Supported by Alkoxide Bridges. Journal of the Chemical Society, Dalton Transactions, 23, 3478-3488.
Kaspar, H., Dettmer, K., Gronwald, W., and Oefner P.J. (2008). Automated GC–MS Analysis of Free Amino Acids in Biological Fluids. Journal of Chromatography B, 870, 222-232.
Kovach, P. M., Meyerhoff, M. E. (1982). Development and Application of a Histidine-Selective Biomembrane Electrode. Analytical Chemistry. 54(2), 217-220.
Liu, Z., Yang, Z., Li, T., Wang, B., Li, Y., Qin, D. Wang, M. Yana, M. (2011). An Effective Cu(II) Quenching Fluorescence Sensor in Aqueous Solution and 1D Chain Coordination Polymer Framework. Dalton Transactions, 40, 9370-9373.
Nan, C. G., Ping, W. X., Ping, D. J., Qing, C. H. (1999). A Study on Electrochemistry of Histidine and Its Metabolites based on the Diazo Coupling Reaction. Talanta, 49, 319-330.
Sulliva Jr, D. J., Gluzman, I. Y., Goldberg, D. E. (1996). Plasmodium Hemozoin Formation Mediated by Histidine-Rich Proteins. Science, 271, 219-222.
Tang, F., Wu, K. K., Nie, Z., Ding, L., Liu, Q., Yuan, J., Guo, M., Yao, S. (2008). Quantification of Amino Acid Ionic Liquids Using Liquid Chromatography–Mass Spectrometry. Journal of Chromatography A, 1208, 175-181.
Wada, H.& Fernando, Q.(1971).Determination of Formation Constants of Copper(II)Complexes of (Hydroxyethylidene)diphosphonic Acid with Solid State Cupric Ion-Selective Electrode. Analytical Chemistry, 43(6), 751–755.
Watchasit, S., Suktanarak, P., Suksai, C., Ruangpornvisuti, V., Tuntulani, T. (2014). Discriminate Sensing of Pyrophosphate Using a New Tripodal Tetramine-Based Dinuclear Zn(II) Complex Under an Indicator Displacement Assay Approach. Dalton Transactions, 43, 14701-14709.
Wiskur, S.L., Ait-Haddou, H., Lavigne, J.J., Anslyn, E.V. (2001). Teaching Old Indicators New Tricks. Accounts of Chemical Research, 34(12), 963-972.
Zhang, J., Sun L., Yoshida T. (2011). Spectroelectrochemical Studies on Redox Reactions of Eosin Y and Its Polymerization with Zn2+ Ions. Journal of Electroanalytical Chemistry, 662, 384-395.
Downloads
Published
2016-10-10
Issue
Section
Research Article
