Copper(II) ion as modulator of the conformation of non-steroidal anti-inflammatory drugs. Theoretical insight into the structure

Zhang, 2003, New metal complexes as potential therapeutics, Curr. Opin. Chem. Biol., 7, 481, 10.1016/S1367-5931(03)00081-4 Drewry, 2011, Recent advances in biosensory and medicinal therapeutic applications of zinc(II) and copper(ii) coordination complexes, Coord. Chem. Rev., 255, 459, 10.1016/j.ccr.2010.10.018 Marzano, 2009, Copper complexes as anticancer agents, Anti Cancer Agents Med. Chem., 185, 10.2174/187152009787313837 Tisato, 2010, Copper in diseases and treatments, and copper-based anticancer strategies, Med. Res. Rev., 30, 708 Kovala-Demertzi, 2000, Transition metal complexes of diclofenac with potentially interesting anti-inflammatory activity, J. Inorg. Biochem., 79, 153, 10.1016/S0162-0134(99)00175-0 Kovala-Demertzi, 2011, Synthesis, crystal structures and spectroscopy of meclofenamic acid and its metal complexes with manganese(ii), copper(ii), zinc(ii) and cadmium(II). Antiproliferative and superoxide dismutase activity, J. Inorg. Biochem., 105, 1187, 10.1016/j.jinorgbio.2011.05.025 Roy, 2006, Direct binding of Cu(II)-complexes of oxicam NSAIDs with DNA backbone, Inorg. Biochem., 100, 1320, 10.1016/j.jinorgbio.2006.03.006 Herendeen, 2003, Use of NSAIDs for the chemoprevention of colorectal cancer, Ann. Pharmacother., 37, 1664, 10.1345/aph.1C489 Rao, 2004, NSAIDs and chemoprevention, Curr. Cancer Drug Targets, 4, 29, 10.2174/1568009043481632 Sporn, 2000, Chemoprevention of cancer, Carcinogenesis, 21, 525, 10.1093/carcin/21.3.525 Grossman, 2000, The role of cyclooxygenase enzymes in the growth of human gall bladder cancer cells, Carcinogenesis, 21, 1403, 10.1093/carcin/21.7.1403 Ritland, 1999, Chemoprevention of intestinal adenomas in the Apc(Min) mouse by piroxicam: kinetics, strain effects and resistance to chemosuppression, Carcinogenesis, 20, 51, 10.1093/carcin/20.1.51 de Groot, 2007, Non-steroidal anti-inflammatory drugs to potentiate chemotherapy effects: from lab to clinic, Crit. Rev. Oncol. Hematol., 61, 52, 10.1016/j.critrevonc.2006.07.001 Orido, 2008, Indomethacin decreases arachidonic acid uptake in HCA-7 human colon cancer cells, J. Pharmacol. Sci., 108, 389, 10.1254/jphs.08167SC Weder, 2002, Copper complexes of non-steroidal anti-inflammatory drugs: an opportunity yet to be realized, Coord. Chem. Rev., 232, 95, 10.1016/S0010-8545(02)00086-3 Berenshtein, 1997, Patterns of mobilization of copper and iron following myocardial ischemia: possible predictive criteria for tissue injury, J. Mol. Cell. Cardiol., 29, 3025, 10.1006/jmcc.1997.0535 Kalman, 2015, H4octapa: highly stable complexation of lanthanide(iii) ions and copper(II), Inorg. Chem., 54, 2345, 10.1021/ic502966m Hossain, 2015, Interaction between transition metals and phenylalanine: A combined experimental and computational study, Spectrochim. Acta, Part A, 138, 499, 10.1016/j.saa.2014.11.084 Nose, 2014, Influence of the d orbital occupation on the structures and sequential binding energies of pyridine to the late first-row divalent transition metal cations: a DFT study, J. Phys. Chem. A, 118, 8129, 10.1021/jp500488t Hosokawa, 2004, Isostructurality among five solvates of phenylbutazone, Cryst. Growth Des., 4, 1195, 10.1021/cg049923m Sanphui, 2011, Phase transformation in conformational polymorphs of nimesulide, J. Pharm. Sci., 100, 2287, 10.1002/jps.22464 Nawaz, 2008, Isopropyl 2-[2-(2,6-dichloroanilino)-phenyl]acetate, Acta Cryst., E64, o334 Luger, 1996, Structure and physicochemical properties of meloxicam, a new NSAID, Eur. J. Pharm. Sci., 4, 175, 10.1016/0928-0987(95)00046-1 Allen, 2002, The Cambridge structural database: a quarter of a million crystal structures and rising, Acta Cryst., B58, 380, 10.1107/S0108768102003890 Frisch, 2010 Keith, T. A. TK Gristmill Software, Overland Park KS, USA, 2014. (aim.tkgristmill.com). Bader, 1990 Bader, 2009, Bond paths are not chemical bonds, J. Phys. Chem. A, 113, 10391, 10.1021/jp906341r Bader, 2010, Definition of molecular structure: by choice or by appeal to observation?, J. Phys. Chem. A, 114, 7431, 10.1021/jp102748b Bader, 1984, The characterization of atomic interactions, J. Chem. Phys., 80, 1943, 10.1063/1.446956 Popelier, 1994, Effect of twisting a polypeptide on its geometry and electron distribution, J. Phys. Chem., 98, 4473, 10.1021/j100067a040 Popelier, 1998, Characterization of a dihydrogen bond on the basis of the electron density, J. Phys. Chem., 102, 1873, 10.1021/jp9805048 Espinosa, 1998, Hydrogen bond strengths revealed by topological analyses of experimentally observed electron densities, Chem. Phys. Lett., 285, 170, 10.1016/S0009-2614(98)00036-0 Espinosa, 2001, About the evaluation of the local kinetic, potential and total energy densities in closed-shell interactions, Chem. Phys. Lett., 336, 457, 10.1016/S0009-2614(01)00178-6 Rozas, 2000, Behavior of ylides containing N, O, and C atoms as hydrogen bond acceptors, J. Am. Chem. Soc., 122, 11154, 10.1021/ja0017864 Espinosa, 2002, From weak to strong interactions: a comprehensive analysis of the topological and energetic properties of the electron density distribution involving X–H F–Y systems, J. Chem. Phys., 117, 5529, 10.1063/1.1501133 Wiberg, 1987, Theoretical analysis of hydrocarbon properties. 2. Additivity of group properties and the origin of strain energy, J. Am. Chem. Soc., 109, 1001, 10.1021/ja00238a005 Chidangil, 1998, A Molecular electrostatic potential mapping study of some fluoroquinolone anti-bacterial agents, J. Mol. Model., 4, 250, 10.1007/s008940050082 Cini, 1990, Metal complexes of the antiinflammatory drug piroxicam, Inorg. Chem., 29, 5197, 10.1021/ic00351a012 Sanatkar, 2013, The meloxicam complexes of Co(II) and Zn(II): synthesis, crystal structures, photocleavage and in vitro DNA-binding, J. Mol. Struct., 1049, 336, 10.1016/j.molstruc.2013.06.070 Tamasi, 2008, Release studies from smart hydrogels as carriers for piroxicam and copper(II)–oxicam complexes as anti-inflammatory and anti-cancer drugs. X-ray structures of new copper(II)–piroxicam and –isoxicam complex molecules, J. Inorg. Biochem., 102, 1862, 10.1016/j.jinorgbio.2008.06.009 Cini, 2007, J. Inorg. Biochem., 101, 1140, 10.1016/j.jinorgbio.2007.04.015 Chakraborty, 2014, Spectroscopic studies of the binding of Cu(II) complexes of oxicam NSAIDs to alternating G–C and homopolymeric G–C sequences, Spectrochim. Acta, 122, 690, 10.1016/j.saa.2013.11.078 Tamasi, 2010, Metal-oxicam coordination compounds: structure, biological activity and strategies for administration, Open Cryst. J., 3, 41, 10.2174/1874846501003020041 Defazio, 2003, Synthesis, X-Ray structural characterization and solution studies of metal complexes containing the anti-inflammatory drugs meloxicam and tenoxicam, Polyhedron, 22, 1355, 10.1016/S0277-5387(03)00112-8 Tamasi, 2010, New platinum-oxicam complexes as anti-cancer drugs. synthesis, characterization, release studies from smart hydrogels, evaluation of reactivity with selected proteins and cytotoxic activity in vitro, J. Inorg. Biochem., 104, 799, 10.1016/j.jinorgbio.2010.03.010 de Paiva, 2012, Synthesis, spectroscopic characterization, DFT studies and antibacterial assays of a novel silver(i) complex with the anti-inflammatory nimesulide, Polyhedron, 36, 112, 10.1016/j.poly.2012.02.002 Majerz, 2011, The influence of potassium cation on a strong OHO hydrogen bond, Org. Biomol. Chem., 9, 1466, 10.1039/c0ob00763c