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Design and synthesis of new thiobarbituric acid metal complexes as potent protease inhibitors: spectral characterization, thermal analysis and DFT calculations

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Abstract

Five novel metal complexes of thiobarbituric acid (TBAH) have been prepared with the general formulae: [Ti(TBA)2(H2O)2]Cl2·2H2O, [Pd(TBA)2]·4H2O, Na[Ag(TBA)2(H2O)2]·4H2O, [Hg(TBA)2(H2O)2] and [Ce(TBA)2(H2O)3]SO4·H2O. The complexes have been fully characterized employing physicochemical and diverse spectroscopic techniques (IR, UV–Vis, mass and 1H NMR) as well as thermal analysis. Elemental analyses and spectroscopic data have showed that the stoichiometries of all complexes were 1:2. Thermal analysis measurements indicated that the complexes have good thermal stability. Density functional theory calculations were carried out at the B3LYP levels of theory with a double basis set, LANL2DZ basis set for titanium, palladium, cerium atoms, or LANL2MB basis set for silver, mercury atoms and 6-31+G(d,p) basis set for the other atoms. The optimized geometry of the ligand and its complexes was obtained based on the optimized structures. The ligand and its metal complexes act as protease inhibitors and repressed their enzymatic activity significantly.

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References

  1. V.K. Srivastava, R.K. Satsangi, K. Shankar, K. Kishor, Pharmazie 36, 252 (1981)

    CAS  Google Scholar 

  2. J. Agarwal, Y.K. Gupta, K.P. Bhargave, K. Shankar, Ind. J. Chem. 20B, 417 (1981)

    Google Scholar 

  3. M.S. Refat, S.A. El-Korashy, A.S. Ahmed, Spectrochim. Acta Part A 71, 1084 (2008)

    Article  Google Scholar 

  4. A. Maleki, A.A. Jafari, S.Yousefia, Carbohydr. Polym. 175, 409 (2017)

    Article  CAS  Google Scholar 

  5. E.S. Raper, Coord. Chem. Rev. 165, 475 (1997)

    Article  CAS  Google Scholar 

  6. N.N. Golovnev, M.S. Molokeev, S.N. Vereshchagin, V.V. Atuchin, M.Y. Sidorenko, M.S. Dmitrushkov, Polyhedron 70, 71 (2014)

    Article  CAS  Google Scholar 

  7. D.J. Tranchemontagne, J.L. Mendoza-Cortes, M. O’Keeffe, O.M. Yaghi, Chem. Soc. Rev. 38, 1257 (2009)

    Article  CAS  Google Scholar 

  8. S. Natarajan, J.K. Sundar, S. Athimoolam, B.R. Srinivasan, J. Coord. Chem. 64, 2274 (2011)

    Article  CAS  Google Scholar 

  9. K. Biradha, A. Ramanan, J.J. Vittal, Cryst. Growth Des. 9, 2969 (2009)

    Article  CAS  Google Scholar 

  10. Z.M. Zaki, G.G. Mohamed, Spectrochim. Acta Part A 56, 1245 (2000)

    Article  Google Scholar 

  11. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, J. PeterssonBloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 09, Revision C.01 (Gaussian, Wallingford, 2010)

    Google Scholar 

  12. A.D. Becke, J. Chem. Phys. 98, 5648 (1993)

    Article  CAS  Google Scholar 

  13. C. Lee, W. Yang, R.G. Parr, Phys. Rev. 37, 785 (1988)

    Article  CAS  Google Scholar 

  14. P.J. Stephens, F.J. Devlin, C.F. Chabalowski, M.J. Frisch, J. Phys. Chem. 98, 11623 (1994)

    Article  CAS  Google Scholar 

  15. W.J. Hehre, R.F. Stewart, J.A. Pople, J. Chem. Phys. 51, 2657 (1969)

    Article  CAS  Google Scholar 

  16. J.B. Collins, P.V.R. Schleyer, J.S. Binkley, J.A. Pople, J. Chem. Phys. 64, 5142 (1976)

    Article  CAS  Google Scholar 

  17. P.J. Hay, W.R. Wadt, J. Chem. Phys. 82, 299 (1985)

    Article  CAS  Google Scholar 

  18. E.B. Thangam, G.S. Rajkumar, Biotechnol. Appl. Biochem. 35, 149–154 (2002)

    Article  CAS  Google Scholar 

  19. R. Dennington, T.A. Keith, J.M. Millam, GaussView, Version 5.0.9 (Semichem Inc., Shawnee Mission, KS, 2009)

  20. E. Kotb, M.I. Abouel-Hawa, E.Y. Tohamy, K. El-Msalamy, Biologia 68, 797 (2013)

    Article  CAS  Google Scholar 

  21. E. Mendez, M.F. Cerda, J.S. Gancheff, J. Torres, C. Kremer, J. Castiglioni, M. Kieninger, O.N. Ventura, J. Phys. Chem. C 111, 3369 (2007)

    Article  CAS  Google Scholar 

  22. R.I. Bakalska, V.B. Delchev, Acta Chim. Slov. 59, 75 (2012)

    CAS  Google Scholar 

  23. C.A. Téllez Soto, J.M. Ramos, A.C.J. Costa, L.S. Vieira, J.L. Rangel, L. Raniero, P.P. Făvero, T. Lemmaa, G.F. Ondar, O. Versiane, A.A. Martin, Spectrochim. Acta Part A 114, 475 (2013)

    Article  Google Scholar 

  24. S.L. Stefan, B.A. El-Shetary, W.G. Hanna, S.B. El-Maraphy, Microchem. J. 35, 51 (1987)

    Article  CAS  Google Scholar 

  25. K. Nakamato, P.J. Mc Carthy, Spectroscopy and Structure of Metal Chelate Compounds (Wiley, New York, 1968), p. 268

    Google Scholar 

  26. M.Y. Nassar, A.S. Attia, K.A. Alfallous, M.F. El-Shahat, Inorg. Chim. Acta 405, 362 (2013)

    Article  CAS  Google Scholar 

  27. M.Y. Nassar, A.S. Attia, S. Adawy, M.F. El-Shahat, J. Mol. Struct. 1026, 88 (2012)

    Article  CAS  Google Scholar 

  28. M.Y. Nassar, T.Y. Mohamed, I.S. Ahmed, J. Mol. Struct. 1050, 81 (2013)

    Article  CAS  Google Scholar 

  29. W.H. El-Shwiniy, S.A. Sadeek, Spectrochim. Acta Part A 137, 535 (2015)

    Article  CAS  Google Scholar 

  30. C.M. Manna, M.Y. Nassar, D. Tofan, K. Chakarawet, C.C. Cummins, Dalton Trans. 43, 1509 (2014)

    Article  CAS  Google Scholar 

  31. M.Y. Nassar, H.M. Aly, M.E. Moustafa, E.A. Abdelrahman, J. Inorg, Organomet. Polym. 27, 1220 (2017)

    Article  CAS  Google Scholar 

  32. M.Y. Nassar, H.M. Aly, E.A. Abdelrahman, M.E. Moustafa, J. Mol. Struct. 1143, 462 (2017)

    Article  CAS  Google Scholar 

  33. H.M. Aly, M.E. Moustafa, M.Y. Nassar, E.A. Abdelrahman, J. Mol. Struct. 1086, 223 (2015)

    Article  CAS  Google Scholar 

  34. S.A. Sadeek, W.H. El-Shwiniy, J. Iran. Chem. Soc. 14, 1711 (2017)

    Article  CAS  Google Scholar 

  35. E.M. Nour, I.S. Alnami, N.A. Alem, J. Phys. Chem. Solids 53, 197 (1992)

    Article  CAS  Google Scholar 

  36. N. Sultana, M.S. Arayne, S. Gul, S. Shamim, J. Mol. Struct. 975, 285 (2010)

    Article  CAS  Google Scholar 

  37. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, Gaussian 09, Revision A.02 (Gaussian Inc, Wallingford, 2009)

    Google Scholar 

  38. M. H. Jamroz, Vibrational energy distribution analysis, VEDA4 computer program, Poland, 2004

  39. N.N. Golovnev, M.S. Molokeev, L.S. Tarasova, V.V. Atuchin, N.I. Vladimirova, J. Mol. Struct. 1068, 21 (2014)

    Article  Google Scholar 

  40. P. Geerlings, F. De Proft, W. Langenaeker, Chem. Rev. 103, 1793 (2003)

    Article  CAS  Google Scholar 

  41. J.B. Foresman, A. Frisch, Exploring Chemistry with Electronic Structure Methods (Gaussian Inc, Pittsburg, 1995)

    Google Scholar 

  42. G. Socrates, Infrared Characteristic Group Frequencies (Wiley, New York, 1980)

    Google Scholar 

  43. L. Pauling, the Nature of the Chemical Bond (Cornell University Press, Ithaca, 1960)

    Google Scholar 

  44. H. Gokce, S. Bahceli, Spectrochim. Acta Part A 114, 1 (2013)

    Article  Google Scholar 

  45. A. Khansari, M. Enhessari, M. Salavati-Niasari, J. Cluster Sci. 24, 289 (2013)

    Article  CAS  Google Scholar 

  46. W. Kohn, A.D. Becke, R.G. Parr, J. Phys. Chem. 100, 12974 (1996)

    Article  CAS  Google Scholar 

  47. R.G. Parr, R.G. Pearson, J. Am. Chem. Soc. 105, 7512 (1983)

    Article  CAS  Google Scholar 

  48. R.G. Pearson, Proc. Natl. Acad. Sci. U.S.A. 83, 8440 (1986)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge the Central Laboratory of Medicine Ministry for performing the antimicrobial measurements.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Benha University, Benha, 13518, Egypt

    Mostafa Y. Nassar, A. M. El-Sharkawy & S. I. El-Desoky

  2. Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, 44519, Egypt

    Walaa H. El-Shwiniy

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  1. Mostafa Y. Nassar
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  2. Walaa H. El-Shwiniy
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  3. A. M. El-Sharkawy
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  4. S. I. El-Desoky
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Correspondence to Mostafa Y. Nassar.

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Nassar, M.Y., El-Shwiniy, W.H., El-Sharkawy, A.M. et al. Design and synthesis of new thiobarbituric acid metal complexes as potent protease inhibitors: spectral characterization, thermal analysis and DFT calculations. J IRAN CHEM SOC 15, 269–280 (2018). https://doi.org/10.1007/s13738-017-1229-3

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