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Synthesis, thermal, spectral and biological properties of zinc(II) 4-hydroxybenzoate complexes

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Abstract

New zinc(II) 4-hydroxybenzoate complex compounds with general formula [Zn(4-OHbenz)2Ln]·xH2O, where 4-OHbenz = 4-hydroxybenzoate; L = isonicotinamide, N-methylnicotinamide, N,N-diethylnicotinamide, thiourea, urea, phenazone, theophylline, methyl-3-pyridylcarbamate; n = 2, 3; x = 0–3, 5, were synthesized and characterised by elemental analysis, thermal analysis and IR spectroscopy. The thermal behaviour of the prepared compounds was studied by TG/DTG and DTA methods in argon atmosphere. The thermal decomposition of hydrated compounds started with dehydration. During the thermal decomposition, organic ligand, carbon monoxide, carbon dioxide and phenol were evolved. The final solid product of the thermal decomposition was zinc or zinc oxide. The volatile gaseous product, solid intermediate products and the final product of thermal decomposition were identified by IR spectroscopy, mass spectrometry, qualitative chemical analyses and X-ray powder diffraction method. The antimicrobial activity of zinc(II) carboxylate compounds was tested against various strains of bacteria, yeasts and filamentous fungi (S. aureus, E. coli, C. parapsilosis, R. oryzae, A. alternata, M. gypseum). The presence of zinc in complexes led to the increase in their antimicrobial activity in comparison with free 4-hydroxybenzoic acid.

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References

  1. Kendrick MJ, May MT, Plishka MJ, Robinson KD. Metals in biological systems. London: Ellis Horwood Limited; 1992.

    Google Scholar 

  2. Van Hoogdalem EJ. Transdermal absorption of topical anti-acne agents in man; review of clinical pharmacokinetic data. J Eur Acad Dermatol Venereol. 1998;11:13–9.

    Article  Google Scholar 

  3. Kulandai Raja Balan AM, Vasanthi M, Prabu R, Paulraj A, Ramachandramoorthy T. Complexes of Ni(II), Cu(II) and Zn(II) benzoates with nicotinanilide. Int J Modern Chem. 2013;4:66–78.

    Google Scholar 

  4. Russell D, Russell AD. Treatment of ringworm: old remedy vs. new. J Infect. 1992;24:333–9.

    Article  CAS  Google Scholar 

  5. Dendrinou-Samara C, Tsotsou G, Ekateriniadou LV, Kortsaris AH, Raptopoulou CP, Terzis A, Kyriakidis DA, Kessissoglou DP. Anti-inflammatory drugs interacting with Zn(II), Cd(II) and Pt(II) metal ions. J Inorg Biochem. 1998;71:171–9.

    Article  CAS  Google Scholar 

  6. Sorenson JRJ, Kishore V, Pezeshk A, Oberley LW, Leuthauser SWC, Oberley TD. Copper complexes: a physiological approach to the treatment of inflammatory diseases. Inorg Chim Acta. 1984;91:285–94.

    Article  CAS  Google Scholar 

  7. Diamantis W, Kohlhepp WC, Haertlein B, Melton J, Sofia RD. Meseclazone, 5-chlorosalicylic acid and acetylsalicylic acid. Comparsion of their effects on in vitro and ex vivo platet aggregation. Thromb Haemost. 1978;40:24–36.

    CAS  Google Scholar 

  8. Zeleňák V, Győryová K, Mlynarčík D. Antibacterial and anti-fungal activity of zinc(II) carboxylates with/without N-donor organic ligands. Metal Based Drugs. 2002;8:269–74.

    Article  Google Scholar 

  9. Barnes PJ, Drazen JM, Rennard SI, Thomson NC. Asthma and COPD: basic mechanisms and clinical management. 2nd ed. London: Elsevier; 2009. p. 627.

    Book  Google Scholar 

  10. Klingsberg E. The chemistry of heterocyclic compounds—pyridine and its derivatives. New York: Wiley; 1962.

    Book  Google Scholar 

  11. Kay Brune MD. The early history of non-opionid analgesics. Acute Pain. 1987;1:33–40.

    Article  Google Scholar 

  12. Tarushki A, Psomas G, Raptopolou CP, Kessissoglou DP. Zinc complexes of the antibacterial drug oxolinic acid. Structure and DNA-binding properties. J Inorg Biochem. 2009;103:898–905.

    Article  CAS  Google Scholar 

  13. Klug HP, Alexander LE, Sumner GG. The crystal structure of zinc salicylate dihydrate. Acta Crystallogr. 1958;11:41–6.

    Article  CAS  Google Scholar 

  14. Brownless NJ, Edwards DA, Mahon MF. Some complexes derived from zinc salicylate or 3,5-di-tert-butylsalicylate. Inorg Chim Acta. 1999;287:89–94.

    Article  CAS  Google Scholar 

  15. Lemoine P, Viossat B, Dung HD, Tomas A, Morgant G, Greenaway FT, Sorenson JRJ. Synthesis, crystal structures, and anti-convulsant activities of ternary [ZnII(3,5-diisopropylsalicylate)2], [ZnII(salicylate)2] and [ZnII(aspirinate)2] complexes. J Inorg Biochem. 2004;98:1734–49.

    Article  CAS  Google Scholar 

  16. Sokolík J, Tumová I, Blahová M, Švajnelová O, Švec P. Anti-inflammatory activity of copper(II) and zinc(II) 3,6-dimethylsalicylates and their equimolar mixture. Acta Facultatis Pharm Universitatis Comenianae. 2006;53:224–8.

    Google Scholar 

  17. Olczak-Kobza M, Czylkowski R, Karolak-Wojciechowska J. Zinc(II)di(o-hydroxybenzoate) complexes with imidazole and its derivatives. J Therm Anal Calorim. 2003;74:895–904.

    Article  CAS  Google Scholar 

  18. Olczak-Kobza M, Mrozek A. Zinc(II) and cadmium(II) complexes with o-hydroxybenzoic acid or o-aminobenzoic acid and 2-methylimidazole. J Therm Anal Calorim. 2009;96:553–60.

    Article  CAS  Google Scholar 

  19. Chomič J, Győryová K, Szunyogová E, Kovářová J. Thermal study of Zinc(II) salicylate complex compounds with bioactive ligands. J Therm Anal Calorim. 2004;76:33–41.

    Article  Google Scholar 

  20. Bujdošová Z, Győryová K, Kovářová J, Hudecová D, Halás L. Synthesis, biological and physicochemical properties of Zinc(II) salicylate and 5-chlorosalicylate complexes with theophylline and urea. J Therm Anal Calorim. 2009;98:151–9.

    Article  CAS  Google Scholar 

  21. Bujdošová Z, Győryová K, Mudroňová D, Hudecová D, Kovářová J. Thermoanalytical investigation and biological properties of zinc(II) 4-chloro- and 5-chlorosalicylates with N-donor ligands. J Therm Anal Calorim. 2012;110:167–76.

    Article  CAS  Google Scholar 

  22. Bujdošová Z, Győryová K, Hudecová D, Kovářová J, Halás L. Preparation, spectral, thermal, and biological properties of zinc(II) 4-chloro- and 5-chlorosalicylate complexes with methyl-3-pyridylcarbamate and phenazone. Chem Papers. 2010;64:584–91.

    Article  CAS  Google Scholar 

  23. Köse DA, Necefoğlu H. Synthesis and characterization of bis(nicotinamide) m-hydroxybenzoate complex of Co((II), Ni(II), Cu(II) and Zn(II). J Therm Anal Calorim. 2008;93:509–14.

    Article  CAS  Google Scholar 

  24. Köse DA, Necefoğlu H, Şahin O, Büyükgüngör O. Synthesis, structural, spectroscopic characterization, and structural comparison of 3-hydroxybenzoate and nicotinamide/N,N-diethylnicotinamide mixed ligand complex with zinc (II). J Therm Anal Calorim. 2012;110:1233–41.

    Article  CAS  Google Scholar 

  25. Zaman IG, Debas NC, Necefoğlu H, Hökelek T. trans-Tetraaquabis(isonicotinamide-κN1) bis(3-hydroxybenzoate) tetrahydrate. Acta Cryst E. 2013;69:m198–9.

    Article  CAS  Google Scholar 

  26. Icbudak H, Heren Z, Köse DA, Necefoğlu H. bis(nicotinamide) and bis(N,N-diethylnicotinamide) p-hydroxybenzoate complex of Ni(II), Cu(II) and Zn(II) Spectrothermal studies. J Therm Anal Calorim. 2004;76:837–51.

    Article  CAS  Google Scholar 

  27. Tyrakowska B, Soffers AEMF, Szymusiak H, Boeren S, Boersma MG, Lemanska K, Vervoort J, Rietjens IMCM. TEAC antioxidant activity of 4-hydroxybenzoates. Free Rad Biol Med. 1999;27:1427–36.

    Article  CAS  Google Scholar 

  28. Jantová S, Hudecová D, Stankovský Š, Špirková K, Ružeková Ľ. Antibacterial effect of substituted 4-quinazolylhydrazines and their arylhydrazones determined by a modified microdilution method. Folia Microbiol. 1995;40:611–4.

    Article  Google Scholar 

  29. Betina V, Mičeková D. Antimicrobial properties of fungal macrolide antibiotics. Z Allg Mikrobiol. 1972;5:355–64.

    Article  Google Scholar 

  30. Hudecová D, Jantová S, Melník M, Uher M. New azidometalkojates and their biological activity. Folia Microbiol. 1996;40:473–6.

    Article  Google Scholar 

  31. Dudová B, Hudecová D, Pokorný R, Mičková M, Palicová M, Segľa P, Melník M. Copper complexes with bioactive ligands. Part II—antifungal activity. Folia Microbiol. 2002;47:225–9.

    Article  Google Scholar 

  32. Graselli JP, Ritchey WM. Atlas of spectral data and physical constants for organic compounds. Ohio: CRC Press; 1975.

    Google Scholar 

  33. Nakamoto K. Infrared and raman spectra of inorganic and coordination compounds. New York: Wiley; 1997.

    Google Scholar 

  34. Lewandowski W, Kalinowska M, Lewandowska H. The ifluence of metals on the eletronic system of biologically important ligands. Spectroscopic studies of benzoates, salicylates, nicotinates and isoorotates. Review. J Inorg Biochem. 2005;99:1407–23.

    Article  CAS  Google Scholar 

  35. Findoráková L, Győryová K, Hudecová D, Mudroňová D, Kovářová J, Homzová K, Nour El-Dien FA. Thermal decomposition study and biological characterization of zinc(II) 2-chlorobenzoate complexes with bioactive ligands. J Therm Anal Calorim. 2013;111:1171–781.

    Article  CAS  Google Scholar 

  36. Zeleňák V, Vargová Z, Győryová K. Correlation of infrared spectra of zinc(II) carboxylates with their structures. Spectrochim Acta. 2007;66:262–72.

    Article  CAS  Google Scholar 

  37. Smith RM. Understanding mass spectra: a basic approach. 2nd ed. New Jersey: Wiley; 2004.

    Book  Google Scholar 

  38. McMurdie H, Morris M, Evans E, Paretzkin B, Wong-Ng W, Ettlinger L, Hubbard C. JCPDS—International Centre for Diffraction Data Task Group on cell parameter refinement. Powder Diffr. 1986;1:66–76.

    Article  Google Scholar 

  39. Krajníková A, Győryová K, Hudecová D, Kovářová J. Thermal decomposition and antimicrobial activity of zinc(II) 2-bromobenzoates with organic ligands. J Therm Anal Calorim. 2011;105:451–60.

    Article  CAS  Google Scholar 

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Acknowledgements

The financial support of VVGS-PF-2013-85 for this study is gratefully acknowledged. The authors thanks to V. Jorík and K. Matelková for XRD powder diffraction measurements.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, P. J. Šafárik University, Moyzesova 11, 041 54, Košice, Slovak Republic

    Katarína Homzová, Katarína Győryová, Mária Ganajová & Zuzana Vargová

  2. Department of Biochemistry and Microbiology, Slovak University of Technology, Radlinského 9, 812 37, Bratislava, Slovak Republic

    Daniela Hudecová

  3. Institute of Macromolecular Chemistry, AS CR, Heyrovsky Sq. 2, 162 06 Prague 6, Prague, Czech Republic

    Jana Kovářová

  4. Department of Chemistry, Biochemistry and Biophysics, University of Veterinary Medicine and Pharmacy in Košice, Komenského 73, 041 81, Košice, Slovak Republic

    Zuzana Bujdošová

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  1. Katarína Homzová
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Correspondence to Katarína Homzová.

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Homzová, K., Győryová, K., Bujdošová, Z. et al. Synthesis, thermal, spectral and biological properties of zinc(II) 4-hydroxybenzoate complexes. J Therm Anal Calorim 116, 77–91 (2014). https://doi.org/10.1007/s10973-014-3702-x

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  • DOI: https://doi.org/10.1007/s10973-014-3702-x

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