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Original Articles

Transition metal complexes of α-aminophosphonates part II: Synthesis, spectroscopic characterization, and in vitro anticancer activity of copper(II) complexes of α-aminophosphonates

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Pages 339-347 | Received 16 Jan 2019, Accepted 14 Nov 2019, Published online: 12 Dec 2019

References

  • Tusek-Bozic, L. Aminophosphonate Metal Complexes of Biomedical Potential. CMC 2013, 20, 2096–2117. DOI: 10.2174/0929867311320160004.
  • Imam, E. A.; El-Sayed, I. E.; Mahfouz, M. G.; Tolba, A. A.; Akashi, T.; Galhoum, A. A.; Guibal, E. Synthesis of α-Aminophosphonate Functionalized Chitosan Sorbents: Effect of Methyl vs. Phenyl Group on Uranium Sorption. Chem. Eng. J. 2018, 352, 1022–1034. DOI: 10.1016/j.cej.2018.06.003.
  • Boshta, N. M.; Elgamal, E. A.; El-Sayed, I. E. Bioactive Amide and α-Amino-Phosphonate Inhibitors for Methicillin-Resistant Staphylococcus Aureus (MRSA). Monatsh. Chem. 2018, 149, 2349–2358. DOI: 10.1007/s00706-018-2303-y.
  • Juribašić, M.; Molčanov, K.; Kojić-Prodić, B.; Bellotto, L.; Kralj, M.; Zani, F.; Tušek-Božić, L. Palladium(II) Complexes of Quinolinylaminophosphonates: Synthesis, Structural Characterization, Antitumor and Antimicrobial Activity. J. Inorg. Biochem. 2011, 105, 867–879. DOI: 10.1016/j.jinorgbio.2011.03.011.
  • Joossens, J.; Ali, O. M.; El-Sayed, I.; Surpateanu, G.; Van der Veken, P.; Lambeir, A.-M.; Setyono-Han, B.; Foekens, J. A.; Schneider, A.; Schmalix, W.; et al. Small, Potent and Selective Diarylphosphonate Inhibitors for Urokinase-Type Plasminogen Activator with in Vivo anti-Metastatic Properties. J. Med. Chem. 2007, 50, 6638–6646. DOI: 10.1021/jm700962j.
  • Aranowska, K.; Graczyk, J.; Checin´Ska, L.; Pakulska, W.; Ochocki, J. Antitumor Effect of Pt(II) Amine Phosphonate Complexes on Sarcoma Sa-180 in Mice. Crystal Structure of Cis-Dichlorobis(Diethyl-4-Pyridylmethylphosphonate-ĸN)Platinum(II) Hydrate, Cis-[PtCl2(4-Pmpe)2] · H2O. Pharmazie 2006, 61, 457–460.
  • Weder, J. E.; Dillon, C. T.; Hambley, T. W.; Kennedy, B. J.; Lay, P. A.; Biffin, J. R.; Regtop, H. L.; Davies, N. M. Copper Complexes of Nonsteroidal anti-Inflammatory Drugs: An Opportunity Yet to Be Realized. Coord. Chem. Rev. 2002, 232, 95–126. DOI: 10.1016/S0010-8545(02)00086-3.
  • Mehta, J. V.; Gajera, S. B.; Raval, D. B.; Thakkar, V. R.; Patel, M. N. Biological Assessment of Substituted Quinoline Based Heteroleptic Organometallic Compounds. Med. Chem. Commun. 2016, 7, 1617–1627. DOI: 10.1039/C6MD00251J.
  • Massoud, S. S.; Louka, F. R.; Ducharme, G. T.; Fischer, R. C.; Mautner, F. A.; Vančo, J.; Herchel, R.; Dvořák, Z.; Trávníček, Z. Copper(II) Complexes Based on Tripodalpyrazolyl Amines: Synthesis, Structure, Magnetic Properties and Anticancer Activity. J. Inorg. Biochem. 2018, 180, 39–46. DOI: 10.1016/j.jinorgbio.2017.11.023.
  • Wehbe, M.; Lo, C.; Leung, A. W. Y.; Dragowska, W. H.; Ryan, G. M.; Bally, M. B. Copper(II) Complexes of Bidentate Ligands Exhibit Potent Anti-Cancer Activity Regardless of Platinum Sensitivity Status. Invest. New Drugs 2017, 35, 682–690. DOI: 10.1007/s10637-017-0488-2.
  • Santini, C.; Pellei, M.; Gandin, V.; Porchia, M.; Tisato, F.; Marzano, C. Advances in Copper Complexes as Anticancer Agents. Chem. Rev. 2014, 114, 815–862. DOI: 10.1021/cr400135x.
  • Konarikova, K.; Andrezalova, L.; Rapta, P.; Slovakova, M.; Durackova, Z.; Laubertova, L.; Gbelcova, H.; Danisovic, L.; Bohmer, D.; Ruml, T.; et al. Effect of the Schiff Base Complex Diaqua-(N-Salicylidene-l-Glutamato)Copper(II) Monohydrate on Human Tumor Cells. Eur. J. Pharmacol. 2013, 721, 178–184. DOI: 10.1016/j.ejphar.2013.09.038.
  • Tardito, S.; Bussolati, O.; Maffini, M.; Tegoni, M.; Giannetto, M.; Dall'Asta, V.; Franchi-Gazzola, R.; Lanfranchi, M.; Pellinghelli, M. A.; Mucchino, C.; et al. Thioamido Coordination in a Thioxo-1,2,4-Triazole Copper(II) Complex Enhances Nonapoptotic Programmed Cell Death Associated with Copper Accumulation and Oxidative Stress in Human Cancer Cells. J. Med. Chem. 2007, 50, 1916–1924. DOI: 10.1021/jm061174f.
  • Creaven, B. S.; Duff, B.; Egan, D. A.; Kavanagh, K.; Rosair, G.; Thangella, V. R.; Walsh, M. Anticancer and Antifungal Activity of Copper(II) Complexes of Quinolin-2(1H)-One-Derived Schiff Bases. Inorg. Chim. Acta 2010, 363, 4048–4058. DOI: 10.1016/j.ica.2010.08.009.
  • Mariano, C.; Pellei, M.; Alidori, S. New Copper(I) Phosphane Complexes of Dihydridobis(3-Nitro-1,2,4-Triazolyl)Borate Ligand Showing Cytotoxic Activity. J. Inorg. Biochem. 2006, 100, 299–304. DOI: 10.1016/j.jinorgbio.2005.11.014.
  • Repicka, Z.; Krupkova, L.; Korabik, M.; Moncol, J.; Hudecova, D.; Valigura, D. Bis(5-Me(O)salicylato) Copper(II) Complexes with/without Diethylnicotinamide – Preparation, Structure and Properties. Acta Chim. Slov. 2009, 2, 52–62.
  • Sohail, S.; Aghmana, R.; Muhammad, A.; Rizwan, H. Synthesis, Characterization and Antibacterial Activity of Nickel(II) and Copper(II) Complexes of N-(Alkyl (Aryl)Carbamothioyl)-4-Nitrobenzamide. Eur. J. Chem. 2010, 3, 200–205. DOI: 10.5155/eurjchem.1.3.200-205.120.
  • Ranford, J. D.; Sadler, P. J.; Tocher, D. A. Cytotoxicity and Antiviral Activity of Transition Metal Salicylato Complexes and Crystal Structure of Bis(Diisopropyl-Salicylato)(1,10-Phenanthroline) Copper(II). J. Chem. Soc. Dalton Trans. 1993, 22, 3393–3399. DOI: 10.1039/dt9930003393.
  • El Sayed, I. E.; El Kosy, S. M.; Hawata, M. A.; El Gokha, A. A.; Tolan, A.; Abd El-Sattar, M. M. Synthesis and Antibacterial Activity of α-Aminophosphonates Bearing Neocryptolepine Moiety. J. Am. Sci. 2011, 7, 357–361.
  • El-Boraey, H. L.; El Sayed, I. E.; El-Gokha, A. A.; Azzam, M. A. Transition Metal Complexes of α-Aminophosphonates. Part I: Synthesis, Spectroscopic Characterization, and In Vitro Anticancer Activity of Copper(II) Complexes of α-Aminophosphonates. Med. Chem. Res. 2015, 24, 2142–2153. DOI: 10.1007/s00044-014-1282-8.
  • Kumar, B. S. TMG Catalysed One Pot Synthesis of α-Aminophosphonates. Arch. Appl. Sci. Res. 2011, 3, 37‒43.
  • Geary, W. J. The Use of Conductivity Measurements in Organic Solvents for the Characterisation of Coordination Compounds. Coord. Chem. Rev. 1971, 7, 81–122. DOI: 10.1016/S0010-8545(00)80009-0.
  • Shebl, M.; Khalil, M. E.; Al-Gohani, F. S. Preparation, Spectral Characterization and Antimicrobial Activity of Binary and Ternary Fe(III), Co(II), Ni(II), Cu(II), Zn(II), Ce(III) and UO2(VI) Complexes of a Thiocarbohydrazone Ligand. J. Mol. Struct. 2010, 980, 78–87. DOI: 10.1016/j.molstruc.2010.06.040.
  • Yeh, C. W.; Chang, K. H.; Hu, C. Y.; Hsu, W.; Chen, J. D. Syntheses, Structures and Ligand Conformations of Cu(II), Co(II) and Ag(I) Complexes Containing the Phosphinicamide Ligands. Polyhedron 2012, 31, 657–664. DOI: 10.1016/j.poly.2011.10.022.
  • Chandra, S.; Gupta, L. K. Modern Spectroscopic Techniques in the Characterization of Schiff Base Macrocyclic Ligand and Its Complexes with Transition Metals. Spectrochim. Acta A 2005, 62, 307‒312. DOI: 10.1016/j.saa.2004.12.044.
  • Ihan, S.; Tamel, H.; Kilic, A.; Tas, E. Synthesis and Spectral Characterization of Macrocyclic Ni(II) Complexes Derived from Various Diamines, Ni(II) Perchlorate and 1,4-Bis(2-Carboxyaldehydephenoxy)Butane. Trans. Met. Chem. 2007, 32, 1012–1017. DOI: 10.1007/s11243-007-0260-0.
  • Igawa, S.; Hashimoto, M.; Kawata, I.; Yashima, M.; Hoshinoa, M.; Osawa, M. Highly Efficient Green Organic Light Emitting Diodes Containing Luminescent Tetrahedral Copper(I) Complexes. J. Mater. Chem. 2013, 1, 542–551. DOI: 10.1039/C2TC00263A.
  • Shimizu, I.; Morimoto, Y.; Faltermeier, D.; Kerscher, M.; Paria, S.; Abe, T.; Sugimoto, H.; Fujieda, N.; Asano, K.; Suzuki, T.; et al. Tetrahedral Copper(II) Complexes with a Labile Coordination Site Supported by a Tris-Tetramethylguanidinato Ligand. Inorg. Chem. 2017, 56, 9634–9645. DOI: 10.1021/acs.inorgchem.7b01154.
  • Tounsi, N.; Dupont, L.; Mohamadou, A.; Guillon, E.; Aplincour, M.; Rogez, G. Synthesis of New Cu(II), Ni(II) and Co(II) Complexes with a Bis-Amide Ligand Functionalized with Pyridine Moieties: Spectral, Magnetic and Electrochemical Studies. Polyhedron 2008, 27, 3674–3682. DOI: 10.1016/j.poly.2008.09.020.
  • Hathaway, B. J.; Billing, D. E. The Electronic Properties and Stereochemistry of Mononuclear Complexes of the Copper(II) Ion. Coord. Chem. Rev. 1970, 5, 143–207. DOI: 10.1016/S0010-8545(00)80135-6.
  • El-Boraey, H. A. Coordination Behavior of Tetraaza [N4] Ligand Towards Co(II), Ni(II), Cu(II), Cu(I) and Pd(II) Complexes: Synthesis, Spectroscopic Characterization and Anticancer Activity. Spectrochim. Acta A 2012, 97, 255–262. DOI: 10.1016/j.saa.2012.05.077.
  • El-Boraey, H. A.; El-Din, A. A. S.; El Sayed, I. New Complexes with 19-Membered Pyridine Based Macrocycle Ligand. J. Therm. Anal. Calorim. 2017, 129, 1243–1253. DOI: 10.2174/1874842201805010051.
  • Dehghanpour, S.; Asadizadeh, S.; Assoud, J. Dinuclear Five-Coordinate Copper(II) Complexes with Chelating Diphosphonic Acid Ligands: Hydrothermal Synthesis, Structure, and Thermal Properties. Z Anorg. Allg. Chem. 2012, 638, 861–867. DOI: 10.1002/zaac.201100495.
  • Maniam, P.; Stock, N. Synthesis and Characterization of the Mixed-Linker Copper(II) Coordination Polymer [Cu(HO3PC6H4SO3)(C10N2H8)] · H2O. Z Anorg. Allg. Chem. 2011, 637, 1145–1151. DOI: 10.1002/zaac.201100202.
  • Bharat, K.; Tripuramallu, Ravada, K.; Das, S. Synthesis, Structural Characterization and Properties of One-Dimensional Coordination Polymers of Cobalt(II)- and Nickel(II)-Phosphonate Complexes with 2,2′-Bipyridine as a Secondary Ligand Component: Observation of Both Cis and Trans Conformations of a Diphosphonic Acid. Polyhedron 2010, 29, 2985–2990. DOI: 10.1016/j.poly.2010.08.008.
  • Mosmann, T. Rapid Colorimetric Assay for Cellular Growth and Survival: Application to Proliferation and Cytotoxicity Assays. J. Immunol. Methods 1983, 65, 55–63. DOI: 10.1016/0022-1759(83)90303-4.
  • Fields, E. J. Multicomponent Reactions: Concepts and Applications for Design and Synthesis. J. Am. Chem. Soc. 1952, 74, 1528‒1531. DOI: 10.1021/ja01126a054.
  • Allmann, R.; Pies, W.; Weiss, A.; D7667, X. 1.1 Simple Oxo Compounds of Aluminium (Oxoaluminates). Izv. Akad. Nauk. SSSR, Ser. Chim. 1953, 6, 1126–1128. DOI: 10.1007/10201551_22.
  • Gao, G.; Chen, M.-N.; Mo, L.-P.; Zhang, Z.-H. Catalyst Free One-Pot Synthesis of α-Aminophosphonates in Aqueous Ethyl Lactate. Phosphorus, Sulfur Silicon Relat. Elem. 2019, 194, 528–532. DOI: 10.1080/10426507.2018.1542395.
  • Abdel-Megeed, M. F.; Badr, E. B.; Azaam, M. M.; El-Hiti, G. A. Synthesis and Antimicrobial Activities of Diphenyl(Arylamino)(1-Phenyl-3-(Pyridin-2-yl)-1H-Pyrazol-4-yl) Methylphosphonates. Phosphorus, Sulfur Silicon Relat. Elem. 2012, 187, 1462‒1468. DOI: 10.1080/10426507.2012.690117.

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