Year 2024,
, 410 - 425, 31.08.2024
Salih Günnaz
,
Khan Mohammad Rahmat
,
Sevil İrişli
Project Number
FYL-2019-20437
References
- [1] Ganjali, MR, Tavakoli, M, Faridbod, F, Riahi, S, Norouzi, P, Niassari, MS. 2008. Interaction Study of a new Bis-Bidentate Schiff's Base with some Metal Ions and its Application in Fabrication of Sm(III) Potentiometric Membrane Sensor. International Journal of Electrochemcal Science, 3: 1559-1573.
- [2] Vigato, PA, Magro PA, Crociani, L, Prinzivalli, C, Zanonato, L, Tamburini, S. 2014. Coordination ability of free or silica immobilized Schiff bases towards Hg(II), Cd(II) and Pb(II) ions. Inorganica Chimica Acta, 410: 29-38.
- [3] Ramírez, P, Contreras, R, Valderrama, M, Carmona, D, Lahoz, FJ, Balana, AI. 2008. Cyclometallated platinum (II) complexes containing the chiral ligand [2-(diphenyl-phosphanyl)-benzylidene]-(1-phenyl-ethyl)-amine: Synthesis and molecular structures of the compounds [PtCl(Me){κ2-(R)-Ph2P(C6H4)=NCH(Ph)Me-P,N}] and [Pt{κ3-(S)-Ph2P(C6H4)CH=NCH(C6H4)Me-P,N,C}Py]BF4. Journal of Organometallic Chemistry; 693(2): 349-356.
- [4] Hayne, DJ, Lim, S, Donnelly, PS. 2014. Metal complexes designed to bind to amyloid-β for the diagnosis and treatment of Alzheimer's disease. Chemical Society Reviews; 43: 6701-6715.
- [5] Khalaji, AD, Jian, FF, Xiao, H, Mojdekanlou, S. 2008. Crystal Structure of N,N`-Bis(3,4,5-trimethoxybenzylidene)ethylenediaminediiodo zinc(II). Analytical Sciences, 24: x91-x92.
- [6] Ghosh, K, Roy, S, Ghosh, S, Banerjee, A, Bauzá, A. 2016. A combined experimental and theoretical study on supramolecular assemblies in octahedral cobalt(III) salicylaldimine complexes having pendant side arms. Polyhedron; 112: 86-95.
- [7] Khalaji, AD, Brad, K, and Zhang, Y. 2008. Diacetonitrile[N,N`-bis(3,4,5-trimethoxybenzylidene)ethylenediamine]copper(I) perchlorate. Acta Crystallographica Section E; 64: m189.
- [8] Subbaraj, P, Ramu, A, Raman, N, Dharmaraja, J. 2015. Synthesis, characterization, DNA interaction and pharmacological studies of substituted benzophenone derived Schiff base metal (II) complexes, Journal of Saudi Chemical Society; 19: 207-216.
- [9] Raman, N, Selvan, A, Sudharsan, S. 2011. Metallation of ethylenediamine based Schiff base with biologically active Cu (II), Ni (II) and Zn (II) ions: synthesis, spectroscopic characterization, electrochemical behaviour, DNA binding, photonuclease activity and in vitro antimicrobial efficacy, Spectrochimica Acta Part A; 79: 873-883.
- [10] Chandra, S, Gautam, S, Rajor, HK, Bhatia, R, 2015. Syntheses, spectroscopic characterization, thermal study, molecular modeling, and biological evaluation of novel Schiff’s base benzil bis(5-amino-1,3,4-thiadiazole-2-thiol) with Ni(II), and Cu(II) metal complexes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; 137: 749-760.
- [11] Reddy, PR, Rajeshwar, S, Satyanarayana, B. 2016. Synthesis, characterization of new copper (ii) Schiff base and 1,10 phenanthroline complexes and study of their bioproperties, Journal of Photochemistry & Photobiology, B: Biology;160: 217-224.
- [12] Collin, F, Sasaki, I, Eury, H, Fuller, P, Hureau, C. 2013. Pt(II) compounds interplay with Cu(II) and Zn(II) coordination to the amyloid-b peptide has metal specific consequences on deleterious processes associated to Alzheimer's disease, Chemical Communications; 49: 2130-2132.
- [13] Sasaki, I, Bijani, C, Ladeira, S, bourdon, V, Faller, P, Hureau C. 2012. Interference of a new cyclometallated Pt compound with Cu binding to amyloid-β peptide, Dalton Transactions; 41(12): 6404-6407.
- [14] McColl G, Roberts BR, Pukala TL, Kenche VB, Roberts CM, Link CD, Ryan TM, Masters CL, Barnham KJ, Bush AI, Cherny RA. 2012. Utility of an improved model of amyloid-beta (Aβ₁₋₄₂) toxicity in Caenorhabditis elegans for drug screening for Alzheimer's disease, Molecular Neurodegeneration; 7: 57.
- [15] Price, JH, Williamson, AN, Schramm, R.F, Wayland, BB. 1972. Palladium(II) and platinum(II) alkyl sulfoxide complexes. Examples of sulfur-bonded, mixed sulfur- and oxygen-bonded, and totally oxygen-bonded complexes, Inorganic Chemistry; 11(6): 1280-1284.
- [16] Ma, G, Huang, F, Pu, X, Jia, L, Jiang, T, Li, L, Liu, Y. 2011. Identification of [PtCl2(phen)] Binding Modes in Amyloid-β Peptide and the Mechanism of Aggregation Inhibition, Chemistry A European Journal; 17: 11657-11666.
- [17] Zhang, XL. 2016. Copper(II) Complexes With Bis-Schiff Bases: Synthesis, Crystal Structures, and Antibacterial Activities, Metal-Organic, and Nano-Metal Chemistry; 46: 1848-1853.
- [18] Bekhit, AA, El-Sayed, OA, Al-Allaf, TAK, Aboul-Enein, HY, Kunhi M, Pulicat, SM, Al-Hussain, K, Al Khodairy, F, Arif, J. 2004. Synthesis, characterization and cytotoxicity evaluation of some new platinum(II) complexes of tetrazolo[1,5-a]quinolines, European Journal of Medicinal Chemistry; 39: 499-505.
- [19] Miles, BA, Patterson, AE, Vogels, CM, Decken, A, Waller, JC, Morin, PJ, Westcott, SA. 2016. Synthesis, characterization, and anticancer activities of lipophilic pyridinecarboxaldimine platinum(II) complexes, Polyhedron; 108: 23-29.
- [20] Gümüş, F, Eren, G, Açık, L, Çelebi, A, Öztürk, F, Yılmaz, Ş, Sağkan, RI, Gür, S, Özkul, A, Elmalı, A, Elerman, Y.2009. Synthesis, Cytotoxicity, and DNA Interactions of New Cisplatin Analogues Containing Substituted Benzimidazole Ligands, Journal of Medicinal Chemistry; 52(5): 1345-1357.
- [21] Jin, L, Sakiyan, İ, Gonzales, NS, Lane, D, Cherala, S. 2014, Synthesis, characterization and Cu2+ binding studies of l-histidine ester of 8-hydroxyquinoline, Inorganica Chimica Acta; 423: 72-78.
Evaluation of Pro-Drug Properties in a Novel Schiff Base-Incorporated Pt(II) Complex
Year 2024,
, 410 - 425, 31.08.2024
Salih Günnaz
,
Khan Mohammad Rahmat
,
Sevil İrişli
Abstract
The present investigation involved the synthesis of a new Schiff base and its platinum complex. The chemical structures of both the ligand and the complex were determined through the utilization of various analytical techniques, including 1H-NMR, 13C-NMR, FT-IR, and elemental analysis. Moreover, the interaction between the synthesized complex and Amyloid-Beta, a crucial factor in the pathogenesis of Alzheimer's disease, was explored. This interaction was assessed by means of fluorescence spectrophotometry. Additionally, the influence of the histidine amino acid, which has been reported in the literature to play a significant role in the interaction between Amyloid-Beta and coordination compounds, was monitored using 1H-NMR. These investigations have the potential to enhance our comprehension of the chemical structure and biological effects of ligands and complexes. Furthermore, they may contribute to the advancement of knowledge regarding important neurodegenerative disorders such as Alzheimer's disease, as well as the development of potential therapeutic strategies.
Ethical Statement
There are no ethical issues regarding the publication of this study
Supporting Institution
Ege University
Project Number
FYL-2019-20437
Thanks
Financial support from Ege University (Project FYL-2019-20437) is gratefully acknowledged.
References
- [1] Ganjali, MR, Tavakoli, M, Faridbod, F, Riahi, S, Norouzi, P, Niassari, MS. 2008. Interaction Study of a new Bis-Bidentate Schiff's Base with some Metal Ions and its Application in Fabrication of Sm(III) Potentiometric Membrane Sensor. International Journal of Electrochemcal Science, 3: 1559-1573.
- [2] Vigato, PA, Magro PA, Crociani, L, Prinzivalli, C, Zanonato, L, Tamburini, S. 2014. Coordination ability of free or silica immobilized Schiff bases towards Hg(II), Cd(II) and Pb(II) ions. Inorganica Chimica Acta, 410: 29-38.
- [3] Ramírez, P, Contreras, R, Valderrama, M, Carmona, D, Lahoz, FJ, Balana, AI. 2008. Cyclometallated platinum (II) complexes containing the chiral ligand [2-(diphenyl-phosphanyl)-benzylidene]-(1-phenyl-ethyl)-amine: Synthesis and molecular structures of the compounds [PtCl(Me){κ2-(R)-Ph2P(C6H4)=NCH(Ph)Me-P,N}] and [Pt{κ3-(S)-Ph2P(C6H4)CH=NCH(C6H4)Me-P,N,C}Py]BF4. Journal of Organometallic Chemistry; 693(2): 349-356.
- [4] Hayne, DJ, Lim, S, Donnelly, PS. 2014. Metal complexes designed to bind to amyloid-β for the diagnosis and treatment of Alzheimer's disease. Chemical Society Reviews; 43: 6701-6715.
- [5] Khalaji, AD, Jian, FF, Xiao, H, Mojdekanlou, S. 2008. Crystal Structure of N,N`-Bis(3,4,5-trimethoxybenzylidene)ethylenediaminediiodo zinc(II). Analytical Sciences, 24: x91-x92.
- [6] Ghosh, K, Roy, S, Ghosh, S, Banerjee, A, Bauzá, A. 2016. A combined experimental and theoretical study on supramolecular assemblies in octahedral cobalt(III) salicylaldimine complexes having pendant side arms. Polyhedron; 112: 86-95.
- [7] Khalaji, AD, Brad, K, and Zhang, Y. 2008. Diacetonitrile[N,N`-bis(3,4,5-trimethoxybenzylidene)ethylenediamine]copper(I) perchlorate. Acta Crystallographica Section E; 64: m189.
- [8] Subbaraj, P, Ramu, A, Raman, N, Dharmaraja, J. 2015. Synthesis, characterization, DNA interaction and pharmacological studies of substituted benzophenone derived Schiff base metal (II) complexes, Journal of Saudi Chemical Society; 19: 207-216.
- [9] Raman, N, Selvan, A, Sudharsan, S. 2011. Metallation of ethylenediamine based Schiff base with biologically active Cu (II), Ni (II) and Zn (II) ions: synthesis, spectroscopic characterization, electrochemical behaviour, DNA binding, photonuclease activity and in vitro antimicrobial efficacy, Spectrochimica Acta Part A; 79: 873-883.
- [10] Chandra, S, Gautam, S, Rajor, HK, Bhatia, R, 2015. Syntheses, spectroscopic characterization, thermal study, molecular modeling, and biological evaluation of novel Schiff’s base benzil bis(5-amino-1,3,4-thiadiazole-2-thiol) with Ni(II), and Cu(II) metal complexes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; 137: 749-760.
- [11] Reddy, PR, Rajeshwar, S, Satyanarayana, B. 2016. Synthesis, characterization of new copper (ii) Schiff base and 1,10 phenanthroline complexes and study of their bioproperties, Journal of Photochemistry & Photobiology, B: Biology;160: 217-224.
- [12] Collin, F, Sasaki, I, Eury, H, Fuller, P, Hureau, C. 2013. Pt(II) compounds interplay with Cu(II) and Zn(II) coordination to the amyloid-b peptide has metal specific consequences on deleterious processes associated to Alzheimer's disease, Chemical Communications; 49: 2130-2132.
- [13] Sasaki, I, Bijani, C, Ladeira, S, bourdon, V, Faller, P, Hureau C. 2012. Interference of a new cyclometallated Pt compound with Cu binding to amyloid-β peptide, Dalton Transactions; 41(12): 6404-6407.
- [14] McColl G, Roberts BR, Pukala TL, Kenche VB, Roberts CM, Link CD, Ryan TM, Masters CL, Barnham KJ, Bush AI, Cherny RA. 2012. Utility of an improved model of amyloid-beta (Aβ₁₋₄₂) toxicity in Caenorhabditis elegans for drug screening for Alzheimer's disease, Molecular Neurodegeneration; 7: 57.
- [15] Price, JH, Williamson, AN, Schramm, R.F, Wayland, BB. 1972. Palladium(II) and platinum(II) alkyl sulfoxide complexes. Examples of sulfur-bonded, mixed sulfur- and oxygen-bonded, and totally oxygen-bonded complexes, Inorganic Chemistry; 11(6): 1280-1284.
- [16] Ma, G, Huang, F, Pu, X, Jia, L, Jiang, T, Li, L, Liu, Y. 2011. Identification of [PtCl2(phen)] Binding Modes in Amyloid-β Peptide and the Mechanism of Aggregation Inhibition, Chemistry A European Journal; 17: 11657-11666.
- [17] Zhang, XL. 2016. Copper(II) Complexes With Bis-Schiff Bases: Synthesis, Crystal Structures, and Antibacterial Activities, Metal-Organic, and Nano-Metal Chemistry; 46: 1848-1853.
- [18] Bekhit, AA, El-Sayed, OA, Al-Allaf, TAK, Aboul-Enein, HY, Kunhi M, Pulicat, SM, Al-Hussain, K, Al Khodairy, F, Arif, J. 2004. Synthesis, characterization and cytotoxicity evaluation of some new platinum(II) complexes of tetrazolo[1,5-a]quinolines, European Journal of Medicinal Chemistry; 39: 499-505.
- [19] Miles, BA, Patterson, AE, Vogels, CM, Decken, A, Waller, JC, Morin, PJ, Westcott, SA. 2016. Synthesis, characterization, and anticancer activities of lipophilic pyridinecarboxaldimine platinum(II) complexes, Polyhedron; 108: 23-29.
- [20] Gümüş, F, Eren, G, Açık, L, Çelebi, A, Öztürk, F, Yılmaz, Ş, Sağkan, RI, Gür, S, Özkul, A, Elmalı, A, Elerman, Y.2009. Synthesis, Cytotoxicity, and DNA Interactions of New Cisplatin Analogues Containing Substituted Benzimidazole Ligands, Journal of Medicinal Chemistry; 52(5): 1345-1357.
- [21] Jin, L, Sakiyan, İ, Gonzales, NS, Lane, D, Cherala, S. 2014, Synthesis, characterization and Cu2+ binding studies of l-histidine ester of 8-hydroxyquinoline, Inorganica Chimica Acta; 423: 72-78.