COMPUȘI COORDINATIVI AI CUPRULUI(II) CU TIOSEMICARBAZONE ALE 2-FORMILPIRIDINEI ȘI DERIVAȚILOR EI

Elena NEGUȚA

Abstract


În articol este efectuată analiza literaturii de specialitate privind sinteza, caracterizarea structurală și proprietățile bio­lo­gice ale compușilor coordinativi ai cuprului(II) în baza tiosemicarbazonelor 2-formilpiridinei și a derivaților ei. A fost stabilit că activitatea biologică a compușilor coordinativi depinde de compoziția și structura complecșilor, în special de natura substituenților din fragmentul piridinic și a substituenților la atomul de azot N(4) ai tiosemicarbazonelor.

 

COPPER(II) COORDINATION COMPOUNDS WITH THIOSEMICARBAZONES OF 2-FORMYLPYRIDINE AND ITS DERIVATIVES

The paper focuses on the analysis of the literature on the synthesis, structural characterisation and biological properties of coordination compounds of copper (II) with 2-formylpyridine thiosemicarbazones and its derivatives. It has been established that biological activity of the coordination compounds dependents on the composition and structure of the complexes, especially on the substituents in the pyridine fragment and on the N(4) nitrogen atom of the thiosemicarbazones.


Keywords


coordination compounds, copper (II), thiosemicarbazones, 2-formylpyridine, crystal structure, biological activity.

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References


HAMEED, A., AL-RASHIDAB, M., UROOSC, M. et. al. Schiff bases in medicinal chemistry: a patent review. In: Expert opinion on therapeutic patents, 2017, no.27(1), p.63-79. https://doi.org/10.1080/13543776.2017.1252752

BHUSHAN, S., PARAS, N.Y. Thiosemicarbazones as Potent Anticancer Agents and their Modes of Action. In: Mini Reviews in Medicinal Chemistry, 2020, no.20(8), p.638-661. https://doi.org/10.2174/1389557519666191029130310

MOMLE, R.G., VEDPATHAK, S.G., KAKADE, G.K. Antimicrobial potential of Schiff base metal complexes: An overview. In: European Journal of Pharmaceutical and Medical Research, 2018, no.5(3), p.225-235.

SIDDIQUI, E.J., AZAD, I., KHAN, A.R., KHAN, T. Thiosemicarbazone Complexes as Versatile Medicinal Chemistry Agents: A Review. In: Journal of Drug Delivery & Therapeutics, 2019, no.9(3), p.689-703. https://doi.org/10.22270/jddt.v9i3.2888

MERLOT, A.M., KALINOWSKI, D.S., and RICHARDSON, D.R. Novel Chelators for Cancer Treatment: Where Are We Now? In: Antioxid. & Redox Signaling, 2013, no.18(8), p.1-34. https://doi.org/10.1089/ars.2012.4540

LIU, M.-C., LIN, T.-S., SARTORELLI, A.C. Chemical and Biological Properties of Cytotoxic α-(N)-Heterocyclic Carboxaldehyde Thiosemicarbazones. In: Progress in Medicinal Chemistry, 1995, no.32, p.1-35. https://doi.org/10.1016/S0079-6468(08)70451-X

FINCH, R.A., LIU, M.-C., GRILL, S.P., ROSE, W.C., LOOMIS, R., VASQUEZ, K.M., CHENG, Y.-C., SARTORELLI, A.C. Triapine (3-Aminopyridine-2-carboxaldehyde-thiosemicarbazone): A Potent Inhibitor of Ribonucleotide Reductase Activity with Broad Spectrum Antitumor Activity. In: Biochemical Pharmacology, 2000, vol.59, p.983–991. https://doi.org/10.1016/S0006-2952(99)00419-0

KUNOS, C.A., CHU, E., MAKOWER, D., KAUBISCH, A., SZNOL, M., IVY, S.P. Phase I Trial of Triapine-Cisplatin-Paclitaxel Chemotherapy for advanced Stage or Metastatic Solid Tumor Cancers. In: Front. Oncol., 2017, 7. Articol on-line. https://doi.org/10.3389/fonc.2017.00062

CASAS, J.S., GARCÍA-TASENDE, M.S., SORDO, J. Main group metal complexes of semicarbazones and thiosemi¬carbazones. A structural review. In: Coord. Chem. Rev., 2000, no.209(1), p.197–261. https://doi.org/10.1016/S0010-8545(00)00363-5

SANTINI, C., PELLEI, M., GANDIN, V., PORCHIA, M., TISATO, F., MARZANO, C. Advances in Copper Complexes as Anticancer. Agents. Chem. Rev., 2014, no114, p.815-862. https://doi.org/10.1021/cr400135x.

TABTI, R., TOUNSI, N., GAIDDON, C., BENTOUHAMI, E., DÉSAUBRY, L. Progress in copper complexes as anticancer agents. Med. Chem., 2017, 7, p.875-879.

GOU, Y., LI, J., FAN, B., XU, B., ZHOU, M., YANG, F. Structure and biological properties of mixed-ligand Cu(II) Schiff base complexes as potential anticancer agents. In: European Journal of Medicinal Chemistry, 2017, vol.134, p.207-217. https://doi.org/10.1016/j.ejmech.2017.04.026

ROGOLINO, D., CAVAZZONI, A., GATTI, A., TEGONI, M., PELOSI, G., VERDOLINO, V., FUMAROLA, C., CRETELLA, D., PETRONINI, P., CARCELLI, M. Anti-proliferative effects of copper(II) complexes with hydroxy-quinoline-thiosemicarbazone ligands. In: European Journal of Medicinal Chemistry, 2017, vol.128, p.140-53. https://doi.org/10.1016/j.ejmech.2017.01.031

WEST, D.X., DIETRICH, S.L., THIENTANAVANICH, I., BROWN, C.A. Copper(II) complexes of 6-methyl-2-formylpyridine 4N-substituted thiosemicarbazones. In: Transition Metal Chemistry, 1994, no.19, p.195-200. https://doi.org/10.1007/BF00161888

ALI, M.A., DEY, K.K., NAZIMUDDIN, M., SMITH, F.E., BUTCHER R.J., et al. The preparation and characterization of some copper(II) complexes of the 6-methyl-2-formylpyridine thiosemicarbazone and the x-ray crystal structure of the chloro(6-methyl-2-formylpyridinethiosemicabazonato)copper(II) complex. In: Polyhedron, 1996, no.15(19), p.3331-3339. https://doi.org/10.1016/0277-5387(96)00003-4

ALI, M.A., IBRAHIM, N.E.H., BUTCHER, R.J., JASINSKI, J.P., JASINSKI, J.M., BRYAN, J.C. Synthesis and charac¬terization of some four- and five-coordinate copper(II) complexes of 6-methyl-2-formylpyridinethiosemicarbazone (HNNS) and the X-ray crystal structures of the [Cu(NNS)(CH3COO)(H2O)] and [Cu(HNNS)(H2O)(SO4)]•H2O complexes. In: Polyhedron, 1998, no.17(11-12), p.1803-1809. https://doi.org/10.1016/S0277-5387(97)00531-7

ALI, M.A., MIRZA, A.H., MONSUR, A., HOSSAIN, S., NAZIMUDDIN, M. Synthesis, characterization, antifungal properties and X-ray crystal structures of five- and six-coordinate copper(II) complexes of the 6-methyl-2-formyl-pyridine4N-dimethylthiosemicar. In: Polyhedron, 2001, no.20, p.1045-1052. https://doi.org/10.1016/S0277-5387(01) 00724-0

DENG, J., YU, P., ZHANG, Z., WANG, J., CAI, J., WU, N., SUN, H., LIANG, H., YANG, F. Designing anticancer copper(II) complexes by optimizing 2-pyridinethiosemicarbazone ligands. In: European Journal of Medicinal Chemistry, 2018, vol.158, p.442-452. https://doi.org/10.1016/j.ejmech.2018.09.020

WEST, D.X., SWEARINGEN, J.K., ROMACK, T.J., BILLEH, I.S., JASINSKI, J.P., LI, Y., STAPLES, R.J. Crystal structures of copper(II) complexes of 2-formylpyridine substituted thiosemicarbazones; the first example of a coor¬dinated thiosemicarbazone with a thiol function. In: Journal of Molecular Structure, 2001, no.570(1-3), p.129-136. https://doi.org/10.1016/S0022-2860(01)00471-9

GOMEZ-SAIZ, P., GIL-GARCIA, R. et al. Unexpected Behaviour of Pyridine-2-carbaldehyde Thiosemicarbazo¬na-tocopper(II) Entities in Aqueous Basic Medium – Partial Transformation of Thioamide into Nitrile. In: Eur. J. Inorg. Chem., 2005, p.3409–3413. https://doi:10.1002/ejic.200500326

AINSCOUGH, E.W., BRODIE, A.M., RANFORD, J.D., WATERS, J.M. Preparation and characterization of complexes of the antitumour copper(II) 2-formylpyridine thiosemicarbazone (HL) system and the single-crystal X-ray structures of [{Cu(HL)(CF3CO2)}2][CF3CO2]2 and [Cu(HL)(H2O)(ClO4)2]•2H2O. In: Chem. Soc. Dalton Trans., 1991, no.8, p.2125-2131. DOI: 10.1039/DT9910002125

GARCÍA-TOJAL, J., GIL-GARCÍA, R., FOUZ, V.I., MADARIAGA, G., LEZAMA, L., GALLETERO, M.S., et al. Revisiting the thiosemicarbazonecopper(II) reaction with glutathione. Activity against colorectal carcinoma cell lines. In: Journal of Inorganic Biochemistry, 2018, vol.180, p.69-79. https://doi.org/10.1016/j.jinorgbio.2017.12.005

GARCIA-TOJALA, J., LEZAMAB, L., PIZARROC, J.L., INSAUSTIB, M., ARRIORTUAC, M.I. Spectroscopic and magnetic properties of copper(II) complexes derived from pyridine-2-carbaldehyde thiosemicarbazone. In: Polyhedron, 1999, no.18, p.3703 –3711. doi:10.1016/s0277-5387(99)00310-1

IBRAHIM, A.B.M., FARH, M.K., EL-GYAR, S.A. Synthesis, structural studies and antimicrobial activities of ma-nganese, nickel and copper complexes of two new tridentate 2-formylpyridine thiosemicarbazone ligands. In: Inorg. Chem. Commun., 2018, vol.96, p.194-201. https://doi.org/10.1016/j.inoche.2018.08.023

IBRAHIM, A.B.M., FARH, M.K., MAYER, P. Copper complexes of new thiosemicarbazone ligands: Synthesis, structural studies and antimicrobial activity. In: Inorg. Chem. Commun., 2018, vol.94, p.127-132. https://doi.org/ 10.1016/j.inoche.2018.06.019

BINGHAM, A.G., BÖGGE, H., MÜLLER, A., et al. Synthetic, Spectroscopic, and X-Ray Crystallographic Studies on Binuclear Copper(II) Complexes with a Tridentate NNS-bonding 2-Formylpyridine Thiosemicarbazone Ligand. The Characterization of Both Neutral and Deprotonated Coordinated Ligand Structures. In: J. Chem. Soc. Dalton Trans., 1987, p.493-499. DOI: 10.1039/DT9870000493

GOMEZ-SAIZ, P., GARCIA-TOJAL, J., MAESTRO, M., MAHIA, J., LEZAMA, L., ROJO, T. Coordination Modes in a (Thiosemicarbazone)copper(II)/Oxalato System-Structures of [{Cu(L)}2(ox)]•2H2O, [Cu(HL)(ox)(H2O)], [{Cu(HL)}2(ox)][Cu(ox)2]•2H2O and [{Cu(HL)}2(ox)](NO3)2 - Ferro- vs. Antiferromagnetic Behavior in Dinuclear Compounds. In: Eur. J. Inorg. Chem., 2003, p.2123-2132. https://doi.org/10.1002/ejic.200200571

GOMEZ-SAIZ, P., et all. Coordination Modes in a Tridentate NNS (Thiosemicarbazonato)copper(II) System Containing Oxygen-Donor Coligands - Structures of [{Cu(L)(X)}2] (X = Formiato, Propionato, Nitrito). In: Eur. J. Inorg. Chem., 2003, p.518-527. https://doi.org/10.1002/ejic.200390074

QI, J., LIANG, S., GOU, Y., et al. Synthesis of four binuclear copper(II) complexes: Structure, anticancer properties and anticancer mechanism. In: Eur. J. Med. Chem., 2015, no.96, p.360-368. https://doi.org/10.1016/j.ejmech.2015.04.031

GIL-GARCÍA, R., GÓMEZ-SAIZ, P., DÍEZ-GÓMEZ V., et. al. Polymorphism and magnetic properties in thiosemicar¬ba¬zonecopper(II)-sulfate compounds. In: Polyhedron, 2013, no.54, p.243-251. https://doi.org/10.1016/j.poly.2013.02.061

PEDRIDO, R., ROMERO, M.J., BERMEJO, M.R., MARTINEZ-CALVO, M., et al. Coordinative trends of a tridentate thiosemicarbazone ligand: synthesis, characterization, luminescence studies and desulfurization processes. In: Dalton Trans., 2009, p.8329-8340. https://doi.org/10.1039/B908782F

GOMES-SAIZ, P., et al. Indirect evidences of desulfurization of a thiosemicarbazonecopper(II) system in aqueous basic medium. In: Inorg. Chem. Commun., 2005, vol.8, p.259-262. https://doi.org/10.1016/j.inoche.2004.12.016

GIL-GARCIA, R., UGALDE, M., BUSTO, N. Selectivity of a thiosemicarbazonatocopper(II) complex towards duplex RNA. Relevant noncovalent interactions both in solid state and solution. In: Dalton Trans., 2016, no.45, p.18704-18718. https://doi.org/10.1039/C6DT02907H

GIL-GARCÍA, R., GÓMEZ-SAIZ, P., DÍEZ-GÓMEZ, V. Thiosemicarbazonecopper(II) compounds with halide/hexafluo¬rosilicate anions: Structure, water clusters, non-covalent interactions and magnetism. In: Polyhedron, 2014, no.81, p.675-686. https://doi.org/10.1016/j.poly.2014.07.032

GIL-GARCIA, R., FRAILE, R., DONNADIEU, B. Desulfurization processes of thiosemicarbazonecopper(II) derivatives in acidic and basic aqueous media. In: New J. Chem., 2013, no.37, p.3568-3580. https://doi.org/10.1039/C3NJ00321C


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