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Articles

Synthesis, characterization and toxicity of Cu(II) complexes with metformin Schiff-bases

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Pages 79-102 | Received 06 Nov 2016, Accepted 14 Feb 2017, Published online: 17 Mar 2017

References

  • J. R. J. Sorenson J. R. J. Copper complexes offer a physiological approach to treatment of chronic diseases. Prog. Med. Chem, 1989, 26, 437–568.
  • M. Fields, S. Reiser, J. C. Smith, Jr. Effect of copper or insulin in diabetic copper-deficient rats. Exp. Biol. Med, 1983, 173(1), 137–139.
  • S. Sitasawad, M. Deshpande, M. Katdare, S. Tirth, P. Parab. Beneficial effect of supplementation with copper sulfate on STZ-diabetic mice (IDDM). Diab. Res. Clin. Pract, 2001, 52, 77–84.
  • K. H. Thompson, J. Chiles, V. G. Yuen, J. Tse, J. H. McNeil, C. Orvig. Comparison of anti-hyperglycemic effect amongst vanadium, molybdenum and other metal maltol complexes. J. Inorg. Biochem, 2004, 98, 683–690.
  • N. Yasumatsu, Y. Yoshikawa, Y. Adachi, H. Sakurai. Antidiabetic copper(II)-picolinate: Impact of the first transition metal in the metallopicolinate complexes. Bioorg. Med. Chem, 2007, 25, 4917–4922.
  • A. Tanaka, H. Kaneto, T. Miyatsuka, K. Yamamoto, K. Yoshiuchi, Y. Yamasaki, I. Shimomura, T. Matsuoka, M. Matsuhisa. Role of copper ion in the pathogenesis of type 2 diabetes. Endocrin. J, 2009, 56 ( 5), 699–706.
  • A.-S. Abdul-Ghani, A.-L. Abu-Hijleh, N. Nahas, R. Amin. Hypoglycemic effect of copper(II) acetate imidazole complexes. Biol. Trace Elem. Res, 1996, 54, 143–151.
  • E. Račanská, O. Švajlenová, J. Valuške, J. Vančo. Acta Facult. Pharm. Univ. Comenianae, 2006, 53, 200–206.
  • J. Vančo, O. Švajlenová, E. Račanská, J. Muselík, J. Valentová. Antiradical activity of different copper(II) Schiff base complexes and their effect on alloxan-induced diabetes. J. Trace Elem. Med. Biol, 2004, 18, 155–161.
  • D. Stepensky, M. Friedman, W. Srour, I. Raz, A. Hoffman. Preclinical evaluation of pharmacokinetic–pharmacodynamic rationale for oral CR metformin formulation. J. Control. Release, 2001, 71 ( 1), 107–115.
  • S. Subasinghe, A.L. Greenbaum, P. McLean. The insulin-mimetic action of Mn2+: Involvement of cyclic nucleotides and insulin in the regulation of hepatic hexokinase and glucokinase. Biochem. Med, 1985, 34 ( 1), 83–92.
  • M. Zhu, L. Lu, P. Yang, X. Jin. Bis(1,1-di-methylbiguanido)copper(II) octahydrate. Acta Crystallogr, 2002, E58, m217–m219.
  • G. Patrinoiu, L. Patron, O. Carp, N. Stanica. Thermal behaviour of some iron(III) complexes with active therapeutically biguanides. J. Therm. Anal. Calorim, 2003, 72 ( 2), 489–495.
  • R. Olar, M. Badea, E. Cristurean, V. Lazar, R. Cernat, C. Balotescu. Thermal behavior, spectroscopic and biological characterization of Co(II), Zn(II), Pd(II) and Pt(II) complexes with N,N-dimethylbiguanide. J. Therm. Anal. Calorim, 2005, 80 ( 2), 451–455.
  • F. A. Al-Saif, M. S. Refat. Synthesis, spectroscopic, and thermal investigation of transition and non-transition complexes of metformin as potential insulin-mimetic agents. J. Therm. Anal. Calorim, 2013, 111 ( 3), 2079–2096.
  • J. A. Gao. A weak hydrolytical copper(II) complex derived from condensation of N, N‐Dimethylbiguanide with 2‐Pyridinecarbaldehyde synthesis, crystal structure and biological activity. Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 2007, 37 ( 8), 621–625.
  • M. A. Mahmoud, S. A. Zaitone, A. A. Ammar, S. A. Sallam. Synthesis, structure and antidiabetic activity of chromium(III) complexes of metformin Schiff-bases. J. Mol. Struct, 2016, 1108, 60–70.
  • B. N. Figgis, J. Lewis. (Eds: J. lewis R. G. Wilkins), Magnetochemistry of complex compounds in modern coordination chemistry, Interscience: New York, 1960.
  • CS Chem3D Pro, version 5, CambridgeSoft Corporation, www.cambridgesoft.com., 1999.
  • W. J. Geary. The use of conductivity measurements in organic solvents for the characterisation of coordination compounds. Coord. Chem. Rev, 1971, 7, 81–122.
  • K. Nakamoto. Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part II: Applications in Coordination, Organometallic, and Bioinorganic Chemistry, 5th ed. Wiley: New York, 1997.
  • R. Olar, M. Badea, D. Marinescu, E. Iorgulescu, S. Stoleriu. Ni(II) complexes with ligands resulted in condensation of N,N-dimethylbiguanide and pentane-2,4-dione. J. Therm. Anal. Calorim, 2005, 80 ( 2), 363–367.
  • G. Socrates. Infrared characteristic group frequencies, 1st ed. Wiley: New York, 1980.
  • M. M. Abd-Elzaher. Spectroscopic characterization of some tetradentate Schiff bases and their complexes with nickel, copper and zinc. J. Chin. Chem. Soc, 2001, 48, 153–158.
  • R. G. Pearson. Hard and soft acids and bases. J. Am. Chem. Soc, 1963, 85, 3533–3539.
  • A. P. B. Lever. Inorganic Electronic Spectroscopy, 2nd ed., Elsevier: Amsterdam, 1984.
  • S. N. Satyanarayana. Electronic Absorption Spectroscopy and Related Techniques. Universities Press: Hyderabad, 2001.
  • F. A. Cotton, G. Wilkinson. Advanced Inorganic Chemistry, Comprehensive Text, 4th ed. John Wiley and Sons: New York, 1986.
  • B. G. Hathaway, O. E. Billing. The electronic properties and stereochemistry of mono-nuclear complexes of the copper(II) ion. Coord. Chem. Rev, 1970, 5, 143–207.
  • V. Philip, V. Suni, M. R. P. Kurup, M. Nethaji. Novel binuclear copper(II) complexes of di-2-pyridyl ketone N(4)-methyl, N(4)-phenylthiosemi- carbazone: Structural and spectral investigations. Polyhedron, 2005, 24, 1133–1142.
  • A. Sreekanth, M. R. P. Kurup. Structural and spectral studies on four coordinate copper(II) complexes of 2-benzoylpyridine N(4),N(4)-(butane-1,4-diyl)thiosemicarbazone. Polyhedron, 2003, 22, 3321–3332.
  • M. Vaidyanathan, R. Viswanathan, M. Palaniandavar, T. Balasubramanian, P. Prabhaharan, P. T. Muthiah. Copper(II) complexes with unusual axial phenolate coordination as structural models for the active site in galactose oxidase:  X-ray crystal structures and spectral and redox properties of [Cu(bpnp)X] Complexes. Inorg. Chem, 1998, 37, 6418–6427.
  • A. W. Addison. (Eds: K. D. Karlin J. Zubieta), Copper Coordination Chemistry: Biochemical and Inorganic Perspectives. Adenine Press: New York, 1983.
  • P. Bindu, M. R. P. Kurup, T. R. Satyakeerthy. Epr, cyclic voltammetric and biological activities of copper(II) complexes of salicylaldehyde N(4)-substituted thiosemicarbazone and heterocyclic bases. Polyhedron, 1999, 18, 321–331.
  • B. J. Hathaway G. Wilkinson R. D. Gillard J. A. McCleverty. (Eds.), Comprehensive Coordination Chemistry II, vol.5. Pergamon: Oxford, 1987.
  • R. P. John, A. Sreekanth, V. Rajakannan, T. A. Ajith, M. R. P. Kurup. New copper(II) complexes of 2-hydroxyacetophenone N(4)-substituted thiosemicarbazones and polypyridyl co-ligands :structural, electro- chemical and antimicrobial studies. Polyhedron, 2004, 23, 2549–2559.
  • M. B. Ibrahim, R. Suleiman, M. Fettouhi, B. El Ali. A silica-supported palladium-bis(oxazoline) complex efficiently catalyzes the synthesis of cinnamic acid derivatives via Mizoroki–Heck coupling reactions. Trans. Met. Chem, 2017, 42, 1–8.
  • R. Olar, A. Dogaru, D. Marinescu, B. Badea. New vanadyl complexes with metformine derivatives as potential insulin mimetic agents. J. Therm. Anal. Calorim, 2012, 110, 257–262.
  • L. C. Y. Woo, V. G. Yuen, K. H. Thompson, J. H. McNeill, C. Orvig. Vanadyl–biguanide complexes as potential synergistic insulin mimics. J. Inorg. Biochem, 1999, 76 ( 3–4), 251–257.
  • L.-P. Lu, P. Yang, S.-D. Qin, M.-L. Zhu. Bis[1,1-dimethyl biguanide(1–)-κ2N2,N5]copper(II) monohydrate. Acta Cryst, 2004, C60, m219–m220.
  • O. Carp, D. Gingasu, I. Mindru, L. Patron. Thermal decomposition of some copper–iron polynuclear coordination compounds containing glycine as ligand, precursors of copper ferrite. Thermochim. Acta, 2006, 449, 55–60.
  • W. Coats, J. P. Redfern. Kinetic parameters from thermogravimetric data. Nature, 1964, 201, 68–69.
  • H. Arslan, N. Ӧzpozn, N. Tarkan. Kinetic analysis of thermogravimetric data of p-toluidino-p-chlorophenylglyoxime and of some complexes. Thermochim. Acta, 2002, 383, 69–77.

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