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Synthesis, characterization, antimicrobial activity and molecular docking study of transition metal complexes based on azo coumarin and thiosemicarbazone derivative

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Abstract

Mixed ligand metal complexes of Co(II), Fe(III), Cu(II), Zn(II), Cd(II) and Hg(II) metal ions with azo coumarin and thiosemicarbazone derivative have been synthesized. Synthesized ligands were supported by spectroscopic techniques such as IR, 1HNMR, 13CNMR and mass analysis while the structure and probable geometry of metal chelates were explored by FTIR, elemental analysis, molar conductance, mass spectrum, thermogravimetry (TG), and electronic spectra (UV). From thermal studies, activation energy and kinetic parameters (ΔG, ΔH, ΔS) of the complexes were also reported. Synthesized ligands and their metal complexes were studied for antimicrobial potential against various bacterial and fungal pathogens. Further, the antioxidant potential screening was done using 1,1-diphenyl-2-picrylhydrazyl. Synthesized metal complexes displayed modest to excellent antimicrobial potential. The topoisomerase II receptor protein was used for molecular docking of the extraordinary antimicrobial Co and Zn-complex.

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References

  1. J. Sahoo, S.K. Paidesetty, J. Taibah Univ. Med. Sci. 12, 115 (2017). https://doi.org/10.1016/j.jtumed.2016.10.004

    Article  PubMed  Google Scholar 

  2. J. Sahoo, S. Kumar Mekap, P. Sudhir Kumar, J. Taibah, Univ. Sci. 9, 187 (2015). https://doi.org/10.1016/j.jtusci.2014.08.001

    Article  Google Scholar 

  3. C. Ranjan Sahoo, J. Sahoo, M. Mahapatra, D. Lenka, P. Kumar Sahu, B. Dehury, R. Nath Padhy, S. Kumar Paidesetty, Arab. J. Chem. 14, 102922 (2021). https://doi.org/10.1016/j.arabjc.2020.102922

    Article  CAS  Google Scholar 

  4. B. Lake, Coumarin Metabolism 37, 423 (1999). https://doi.org/10.1016/S0278-6915(99)00010-1

    Article  CAS  Google Scholar 

  5. A. Rawat, A. Vijaya Bhaskar Reddy, Eur. J. Med. Chem. Reports. 5, 100038 (2022). https://doi.org/10.1016/j.ejmcr.2022.100038

    Article  CAS  Google Scholar 

  6. I. Kostova, I. Manolov, M. Karaivanova, Arch. Pharm. (Weinheim). 334, 157 (2001). https://doi.org/10.1002/1521-4184(200105)334:5%3c157::AID-ARDP157%3e3.0.CO;2-S

    Article  PubMed  CAS  Google Scholar 

  7. H.-L. Qin, Z.-W. Zhang, L. Ravindar, K.P. Rakesh, Eur. J. Med. Chem. 207, 112832 (2020). https://doi.org/10.1016/j.ejmech.2020.112832

    Article  PubMed  CAS  Google Scholar 

  8. M. Gökalp, B. Dede, T. Tilki, Ç. Karabacak Atay, J. Mol. Struct. 1212, 128140 (2020). https://doi.org/10.1016/j.molstruc.2020.128140

    Article  CAS  Google Scholar 

  9. C.T. Keerthi Kumar, J. Keshavayya, T.N. Rajesh, S.K. Peethambar, A.R. Shoukat Ali, Org. Chem. Int. 2013, 1 (2013). https://doi.org/10.1155/2013/370626

    Article  CAS  Google Scholar 

  10. B.N. Ravi, J. Keshavayya, N.M. Mallikarjuna, V. Kumar, F.N. Zahara, Chem. Data Collect. 33, 100686 (2021). https://doi.org/10.1016/j.cdc.2021.100686

    Article  CAS  Google Scholar 

  11. M. Pervaiz, S. Sadiq, A. Sadiq, U. Younas, A. Ashraf, Z. Saeed, M. Zuber, A. Adnan, Coord. Chem. Rev. 447, 214128 (2021). https://doi.org/10.1016/j.ccr.2021.214128

    Article  CAS  Google Scholar 

  12. H. Kargar, V. Torabi, A. Akbari, R. Behjatmanesh-Ardakani, A. Sahraei, J. Mol. Struct. 1205, 127642 (2020). https://doi.org/10.1016/j.molstruc.2019.127642

    Article  CAS  Google Scholar 

  13. M. Mesbah, T. Douadi, F. Sahli, S. Issaadi, S. Boukazoula, S. Chafaa, J. Mol. Struct. 1151, 41 (2018). https://doi.org/10.1016/j.molstruc.2017.08.098

    Article  ADS  CAS  Google Scholar 

  14. E. Pahlavani, H. Kargar, N.S. Rad, J. Res. Med. Sci. (2015). https://doi.org/10.17795/zjrms1010

    Article  Google Scholar 

  15. P. Sathyadevi, P. Krishnamoorthy, E. Jayanthi, R.R. Butorac, A.H. Cowley, N. Dharmaraj, Inorganica Chim. Acta. 384, 83 (2012). https://doi.org/10.1016/j.ica.2011.11.033

    Article  CAS  Google Scholar 

  16. A.A. Ardakani, H. Kargar, N. Feizi, M.N. Tahir, J. Iran. Chem. Soc. 15, 1495 (2018). https://doi.org/10.1007/s13738-018-1347-6

    Article  CAS  Google Scholar 

  17. H. Kargar, A. Adabi Ardakani, K.S. Munawar, M. Ashfaq, M.N. Tahir, J. Iran. Chem. Soc. 18, 2493 (2021). https://doi.org/10.1007/s13738-021-02207-x

    Article  CAS  Google Scholar 

  18. P.P. Netalkar, S.P. Netalkar, V.K. Revankar, Polyhedron 100, 215 (2015). https://doi.org/10.1016/j.poly.2015.07.075

    Article  CAS  Google Scholar 

  19. N.C. Kasuga, K. Sekino, M. Ishikawa, A. Honda, M. Yokoyama, S. Nakano, N. Shimada, C. Koumo, K. Nomiya, J. Inorg. Biochem. 96, 298 (2003). https://doi.org/10.1016/S0162-0134(03)00156-9

    Article  PubMed  CAS  Google Scholar 

  20. N.M. El Metwally, R. Arafa, U. El-Ayaan, J. Therm. Anal. Calorim. 115, 2357 (2014). https://doi.org/10.1007/s10973-013-3065-8

    Article  CAS  Google Scholar 

  21. N. Bharti, K. Husain, M. Gonzalez Garza, D.E. Cruz-Vega, J. Castro-Garza, B.D. Mata-Cardenas, F. Naqvi, A. Azam, Bioorg. Med. Chem. Lett. 12, 3475 (2002). https://doi.org/10.1016/S0960-894X(02)00703-5

    Article  PubMed  CAS  Google Scholar 

  22. M.S. Refat, I.M. El-Deen, M.S. El-Garib, W. Abd El-Fattah, Russ. J. Gen. Chem. 85, 692 (2015). https://doi.org/10.1134/S1070363215030299

    Article  CAS  Google Scholar 

  23. J.P. Scovill, D.L. Klayman, C.F. Franchino, J. Med. Chem. 25, 1261 (1982). https://doi.org/10.1021/jm00352a036

    Article  PubMed  CAS  Google Scholar 

  24. H. Kaur, B. Narasimhan, Curr. Top. Med. Chem. 18, 3 (2018). https://doi.org/10.2174/1568026618666180206093107

    Article  PubMed  CAS  Google Scholar 

  25. F.G. Parsa, M.A.H. Feizi, R. Safaralizadeh, S.A. Hosseini-Yazdi, M. Mahdavi, J. Biol. Inorg. Chem. 25, 383 (2020). https://doi.org/10.1007/s00775-020-01769-0

    Article  PubMed  CAS  Google Scholar 

  26. M. Kheirkhahi, B. Shaabani, H. Samadi Kafil, J. Iran. Chem. Soc. 18, 3429 (2021). https://doi.org/10.1007/s13738-021-02281-1

    Article  CAS  Google Scholar 

  27. I. Wiegand, K. Hilpert, R.E.W. Hancock, Nat. Protoc. 3, 163 (2008). https://doi.org/10.1038/nprot.2007.521

    Article  PubMed  CAS  Google Scholar 

  28. B. Vivekanand, K. Mahendra Raj, B.H.M. Mruthyunjayaswamy, J. Mol. Struct. 1079, 214 (2015). https://doi.org/10.1016/j.molstruc.2014.08.033

    Article  ADS  CAS  Google Scholar 

  29. G.M. Morris, R. Huey, W. Lindstrom, M.F. Sanner, R.K. Belew, D.S. Goodsell, A.J. Olson, J. Comput. Chem. 30, 2785 (2009). https://doi.org/10.1002/jcc.21256

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  30. A. Hussain, M.A. Rather, M.S. Dar, N.A. Dangroo, M.A. Aga, A. Qayum, A.M. Shah, Z. Ahmad, M.J. Dar, Q.P. Hassan, Microbiol. Res. 207, 196 (2018). https://doi.org/10.1016/j.micres.2017.12.004

    Article  PubMed  CAS  Google Scholar 

  31. D. Steverding, P. Evans, L. Msika, B. Riley, J. Wallington, S. Schelenz, Med. Mycol. 50, 333 (2012). https://doi.org/10.3109/13693786.2011.609186

    Article  PubMed  CAS  Google Scholar 

  32. B.D. Bax, P.F. Chan, D.S. Eggleston, A. Fosberry, D.R. Gentry, F. Gorrec, I. Giordano, M.M. Hann, A. Hennessy, M. Hibbs, J. Huang, E. Jones, J. Jones, K.K. Brown, C.J. Lewis, E.W. May, M.R. Saunders, O. Singh, C.E. Spitzfaden, C. Shen, A. Shillings, A.J. Theobald, A. Wohlkonig, N.D. Pearson, M.N. Gwynn, Nature 466, 935 (2010). https://doi.org/10.1038/nature09197

    Article  ADS  PubMed  Google Scholar 

  33. A. Rai, T.K. Gupta, S. Kini, A. Kunwar, A. Surolia, D. Panda, Biochem. Pharmacol. 86, 378 (2013). https://doi.org/10.1016/j.bcp.2013.05.024

    Article  PubMed  CAS  Google Scholar 

  34. E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng, T.E. Ferrin, J. Comput. Chem. 25, 1605 (2004). https://doi.org/10.1002/jcc.20084

    Article  PubMed  CAS  Google Scholar 

  35. R.M. Mahfouz, K.A. Al-Farhan, G.Y. Hassen, A.I. Al-Wassil, S.M. Alshehri, A.A. Al-Wallan, Synth. React. Inorg. Met. Chem. 32, 489 (2002). https://doi.org/10.1081/SIM-120003791

    Article  CAS  Google Scholar 

  36. P. Jayaseelan, E. Akila, M. Usha Rani, R. Rajavel, J. Saudi Chem. Soc. 20, 625 (2016). https://doi.org/10.1016/j.jscs.2013.07.001

    Article  CAS  Google Scholar 

  37. K.B. Gudasi, M.S. Patil, R.S. Vadavi, Eur. J. Med. Chem. 43, 2436 (2008). https://doi.org/10.1016/j.ejmech.2008.01.028

    Article  PubMed  CAS  Google Scholar 

  38. M.S. Atanassova, G.D. Dimitrov, Spectrochim Acta Part A Mol. Biomol. Spectrosc. 59, 1655 (2003). https://doi.org/10.1016/S1386-1425(02)00397-9

    Article  ADS  CAS  Google Scholar 

  39. A. Karaküçük-İyidoğan, D. Taşdemir, E.E. Oruç-Emre, J. Balzarini, Eur. J. Med. Chem. 46, 5616 (2011). https://doi.org/10.1016/j.ejmech.2011.09.031

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  40. M.B. Ferrari, F. Bisceglie, E. Leporati, G. Pelosi, P. Tarasconi, Bull. Chem. Soc. Jpn 75, 781 (2002). https://doi.org/10.1246/bcsj.75.781

    Article  CAS  Google Scholar 

  41. S.A. Abdel-Latif, A.A. Mohamed, J. Mol. Struct. 1134, 307 (2017). https://doi.org/10.1016/j.molstruc.2016.12.068

    Article  ADS  CAS  Google Scholar 

  42. S. Indira, G. Vinoth, M. Bharathi, K. Shanmuga Bharathi, J. Mol. Struct. 1198, 126886 (2019). https://doi.org/10.1016/j.molstruc.2019.126886

    Article  CAS  Google Scholar 

  43. A. Çapan, S. Uruş, M. Sönmez, J. Saudi Chem. Soc. 22, 757 (2018). https://doi.org/10.1016/j.jscs.2017.12.007

    Article  CAS  Google Scholar 

  44. R.S. Sreepriya, S.S. Kumar, V. Sadasivan, S. Biju, S.S. Meena, J. Mol. Struct. 1201, 127110 (2020). https://doi.org/10.1016/j.molstruc.2019.127110

    Article  CAS  Google Scholar 

  45. P. Mendu, J. Pragathi, B. Anupama, C.G. Kumari, E-J. Chem. 9, 2145 (2012). https://doi.org/10.1155/2012/839789

    Article  CAS  Google Scholar 

  46. R. Takjoo, R. Centore, L. Rhyman, P. Ramasami, J. Coord. Chem. 65, 1569 (2012). https://doi.org/10.1080/00958972.2012.675058

    Article  CAS  Google Scholar 

  47. A.F. Elhusseiny, A. Eldissouky, A.M. Al-Hamza, H.H.A.M. Hassan, J. Mol. Struct. 1100, 530 (2015). https://doi.org/10.1016/j.molstruc.2015.07.049

    Article  ADS  CAS  Google Scholar 

  48. M.A. Farrukh, K.M. Butt, K.-K. Chong, W.S. Chang, J. Saudi Chem. Soc. 23, 561 (2019). https://doi.org/10.1016/j.jscs.2018.10.002

    Article  CAS  Google Scholar 

  49. A. Meena, R. Sharma, V. Sukhadia, Curr. Phys. Chem. 10, 213 (2020). https://doi.org/10.2174/1877946810666200116091321

    Article  CAS  Google Scholar 

  50. S.S. Borhade, P.T. Tryambake, Synth. Asian J. Chem. 33, 885 (2021). https://doi.org/10.14233/ajchem.2021.23110

    Article  CAS  Google Scholar 

  51. S.S. Borhade, P.T. Tryambake, Asian J. Chem. 34, 2041 (2022). https://doi.org/10.14233/ajchem.2022.23728

    Article  CAS  Google Scholar 

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Acknowledgements

The authors would like to express their gratitude to the SAIF at Punjab University Chandigarh for providing the spectral analysis facility.

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Correspondence to Pravin T. Tryambake.

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Borhade, S.S., Tryambake, P.T. Synthesis, characterization, antimicrobial activity and molecular docking study of transition metal complexes based on azo coumarin and thiosemicarbazone derivative. J IRAN CHEM SOC 21, 719–730 (2024). https://doi.org/10.1007/s13738-023-02953-0

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