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Vol. 35 No. 7 (2023): Vol 35 Issue 7 (2023)

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Synthesis, Characterization, Biological Activity and Molecular Docking Studies of Phthalic Acid based Macrocyclic Transition Metal Complexes

https://doi.org/10.14233/ajchem.2023.27926
Rajrani Gulia
Department of Chemistry, Baba Mastnath University, Rohtak-124021, India
Vikas Sangwan
Department of Chemistry, R.P.S. Degree College, Mahendergarh-123029, India
Anshul Singh
Department of Chemistry, Baba Mastnath University, Rohtak-124021, India
https://orcid.org/0000-0003-0962-308X
Sonaxi Kharb
Department of Chemistry, Baba Mastnath University, Rohtak-124021, India
Ritu Solanki
Department of Biochemistry, Maharshi Dayanand University, Rohtak-124001, India

Corresponding Author(s) : Anshul Singh

anshul9008@gmail.com

Asian Journal of Chemistry, Vol. 35 No. 7 (2023): Vol 35 Issue 7 (2023)

Abstract

A novel series of macrocyclic complexes of [M(L)Cl2] (M = Co(II), Ni(II) and Cu(II), L = macrocyclic ligand) were synthesized by template condensation method using 3,4-diaminotoluene and phthalic acid in the presence of divalent transition metal ions e.g., Co(II), Ni(II) and Cu(II) in their chloride form. These synthesized metal complexes were fully characterized by spectroscopic techniques, namely UV-Visible, IR, ESR and ESI-MS. Their thermal behaviour was determined by TGA and DTA. Further these macrocyclic complexes were screened for antimicrobial activity against bacterial species (Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa and Escherichia coli) and fungi (Aspergillus niger and Candida albicans) and then compared against standard drug streptomycin and itraconazole, respectively. In addition to these the antioxidant activity of the macrocyclic complexes were also investigated through scavenging effect on the DPPH radicals. Finally, the biological potency of synthesized compounds was evaluated using Auto Dock Vina. All the synthesized macrocyclic complexes were found to be potent against bacterial and fungal species, which suggest their potential application as antibacterial and antifungal agents.

Keywords

Macrocyclic complexes Template condensation Antimicrobial Tetra-aza macrocyclic Molecular docking
Gulia, R., Sangwan, V., Singh, A., Kharb, S., & Solanki, R. (2023). Synthesis, Characterization, Biological Activity and Molecular Docking Studies of Phthalic Acid based Macrocyclic Transition Metal Complexes. Asian Journal of Chemistry, 35(7), 1632–1644. https://doi.org/10.14233/ajchem.2023.27926
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References
  1. H. Keypour, N. Ansari, M. Mahmoudabadi, R. Karamian, S.H.M. Farida, M.E. Moghadam and R.W. Gable, Inorg. Chim. Acta, 509, 119705 (2020); https://doi.org/10.1016/j.ica.2020.119705
  2. R. Kanaoujiya, D. Kumar Sahu, V. Shankar, Garima and S. Srivastava, Mater. Today Proc., 62, 3497 (2022); https://doi.org/10.1016/j.matpr.2022.04.303
  3. M.M. Keypour, F. Forouzandeh, R. Azadbakht, J. Khanabadi and M.A. Moghadam, J. Mol. Struct., 1232, 130024 (2021); https://doi.org/10.1016/j.molstruc.2021.130024
  4. Y.L. Li, N. Wang, H.T. Lei, X.L. Li, H.Q. Zheng, H.Y. Wang, W. Zhang and R. Cao, Coord. Chem. Rev., 442, 213996 (2021); https://doi.org/10.1016/j.ccr.2021.213996
  5. R. Kanaoujiya, D. Singh, T. Minocha, S.K. Yadav and S. Srivastava, Mater. Today Proc., 65, 3143 (2022); https://doi.org/10.1016/j.matpr.2022.05.354
  6. N. Fahmi, I. Masih and K. Soni, J. Macromol. Sci. A Pure Appl. Chem., 52, 548 (2015); https://doi.org/10.1080/10601325.2015.1039334
  7. M. Krstic, B. Petkovi, M. Mil, D. Mi and J.F. Santibanez, Macedonian Chem. Chem Eng., 38, 1 (2019); https://doi.org/10.20450/mjcce.2019.1599
  8. A.J. Schuman, A. Raghavan, S.D. Banziger, Y. Song, Z.-B. Hu, B.L. Mash, A.L. Williams and T. Ren, Inorg. Chem., 60, 4447 (2021); https://doi.org/10.1021/acs.inorgchem.0c03224
  9. C.J.M. Brown and R.J. Codd, J. Inorg. Biochem., 216, 111337 (2021); https://doi.org/10.1016/j.jinorgbio.2020.111337
  10. T. Joshi, B. Graham and L. Spiccia, Acc. Chem. Res., 48, 2366 (2015); https://doi.org/10.1021/acs.accounts.5b00142
  11. M.O.F. Khan, J. Keiser, P.N.A. Amoyaw, M.F. Hossain, M. Vargas, J.G. Le, N.C. Simpson, K.D. Roewe, T.R.N.C. Freeman, T.R. Hasley, R.D. Maples, S.J. Archibald and T.J. Hubin, Antimicrob. Agents Chemother., 60, 5331 (2016); https://doi.org/10.1128/AAC.00778-16
  12. T.J. Hubin, A.N. Walker, D.J. Davilla, T.R.N. Carder Freeman, B.M. Epley, T.R. Hasley, P.N.A. Amoyaw, S. Jain, S.J. Archibald, T.J. Prior, J.A. Krause, A.G. Oliver, B.L. Tekwani and M.O.F. Khan, Polyhedron, 163, 42 (2019); https://doi.org/10.1016/j.poly.2019.02.027
  13. H. Zafar, A. Kareem, A. Sherwani, O. Mohammad, M.A. Ansari, H.M. Khan and T.A. Khan, J. Photochem. Photobiol. B, 142, 8 (2015); https://doi.org/10.1016/j.jphotobiol.2014.10.004
  14. A. Kareem, H. Zafar, A. Sherwani, O. Mohammad and T.A. Khan, J. Mol. Struct., 1075, 17 (2014); https://doi.org/10.1016/j.molstruc.2014.06.073
  15. E.J.P. Malar, R. Jacob and S. Balasubramanian, J. Chem. Sci., 131, 110 (2019); https://doi.org/10.1007/s12039-019-1688-4
  16. M. Asadi, H. Sepehrpour and K. Mohammadi, J. Serb. Chem. Soc., 76, 63 (2011); https://doi.org/10.2298/JSC100104004A
  17. P. Gull, M.A. Malik, O.A. Dar and A.A. Hashmi, J. Mol. Struct., 1134, 734 (2017); https://doi.org/10.1016/j.molstruc.2017.01.033
  18. J. Li, R. Liu J. Jiang, X. Liang, G. Huang, D. Yang, H. Chen, L. Pan and Z. Ma, J. Inorg. Biochem., 210, 111165 (2020); https://doi.org/10.1016/j.jinorgbio.2020.111165
  19. S. Chandra and Ruchi, Spectrochim. Acta A Mol. Biomol. Spectrosc., 103, 338 (2013); https://doi.org/10.1016/j.saa.2012.10.065
  20. M.A. Nikolic, K.M. Szécsényi, B. Dražic, M.V. Rodic, V. Stanic and S. Tanaskovic, J. Mol. Struct., 1236, 130133 (2021); https://doi.org/10.1016/j.molstruc.2021.130133
  21. P. Rajakkani, A. Alagarraj and S.A.G. Thangavelu, Inorg. Chem. Commun., 134, 108989 (2021); https://doi.org/10.1016/j.inoche.2021.108989
  22. L. Mandal, S. Majumder and S. Mohanta, Dalton Trans., 45, 17365 (2016); https://doi.org/10.1039/C6DT02631A
  23. S. Das, J. Adhikary, P. Chakraborty, T. Chakraborty and D. Das, RSC Adv., 6, 98620 (2016); https://doi.org/10.1039/C6RA05478A
  24. T. Chakraborty, S. Mukherjee, R. Parveen, A. Chandra, D. Samanta and D. Das, New J. Chem., 45, 2550 (2021); https://doi.org/10.1039/D0NJ05635A
  25. S. Ullmann, R. Schnorr, M. Handke, C. Laube, B. Abel, J. Matysik, M. Findeisen, R. Rüger, T. Heine and B. Kersting, Chem. Eur. J., 23, 3824 (2017); https://doi.org/10.1002/chem.201700253
  26. M. Upadhyay, R.V. Singh and N. Fahmi, Res. J. Chem. Sci., 12, 18 (2022).
  27. A. Pilon, J. Lorenzo, S. Rodriguez-Calado, P. Adao, A.M. Martins, A. Valente and L. Alves, ChemMedChem, 14, 770 (2019); https://doi.org/10.1002/cmdc.201800702
  28. N. Fahmi, M. Upadhyay, N. Sharma and S. Belwal, J. Chem. Res., 44, 336 (2020); https://doi.org/10.1177/1747519819893885
  29. N. Ghaffar, S. Javad, M.A. Farrukh, A.A. Shah, M.K. Gatasheh, B.M.A. Al-Munqedhi and O. Chaudhry, PLoS One, 17, e0264588 (2022); https://doi.org/10.1371/journal.pone.0264588
  30. Z. You, X. Ran, Y. Dai and Y.J. Ran, J. Mycol. Med., 28, 492 (2018); https://doi.org/10.1016/j.mycmed.2018.03.007
  31. S. Lamba, M. Agrawal and S. Bugalia, Int. J. Sci. Res., 6, 1488 (2013).
  32. P. Molyneux, Songklanakarin J. Sci. Technol., 26, 211 (2004).
  33. M.D. Hanwell, D.E. Curtis, D. Lonie, C.T. Vandermeersch, E. Zurek and G.R.J. Hutchison, J. Cheminform., 4, 17 (2012); https://doi.org/10.1186/1758-2946-4-17
  34. H.D. Snyder and T.G. Kucukkal, J. Chem. Educ., 98, 1335 (2021); https://doi.org/10.1021/acs.jchemed.0c00959
  35. S. Forli, R. Huey, M.E. Pique, M.F. Sanner, D.S. Goodsell and A.J. Olson, Nat. Protoc., 11, 905 (2016); https://doi.org/10.1038/nprot.2016.051
  36. O. Trott and A.J. Olson, J. Comput. Chem., 31, 455 (2010); https://doi.org/10.1002/jcc.21334
  37. D. Salha, M. Andaç and A. Denizli, J. Mol. Recognit., 34, E2875 (2021); https://doi.org/10.1002/jmr.2875
  38. E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng and T.E. Ferrin, J. Comput. Chem., 25, 1605 (2004); https://doi.org/10.1002/jcc.20084
  39. S. Chauhan, M. Swami, S. Malik and R.V. Singh, Main Group Met. Chem., 31, 263 (2008); https://doi.org/10.1515/MGMC.2008.31.5.263
  40. M.H. Abo-Ghalia, G.O. Moustafa, A.E.G.E. Amr, A.M. Naglah, E.A. Elsayed and A.H. Bakheit, Molecules, 25, 1253 (2020); https://doi.org/10.3390/molecules25051253
  41. I. Masih, N. Fahmi and Rajkumar, J. Enzyme Inhib. Med. Chem., 28, 33 (2013); https://doi.org/10.3109/14756366.2011.625022
  42. O.H.S. Al-Obaidi and A.R. Al-Hiti, Am. Chem. Sci. J., 2, 1 (2012); https://doi.org/10.9734/ACSJ/2012/1063
  43. S.K. Das Gupta, S. Rabi, D. Ghosh, F. Yasmin, B.K. Dey, S. Dey and T.G. Roy, J. Chem. Sci., 133, 7 (2021); https://doi.org/10.1007/s12039-020-01861-7
  44. V. Sangwan and D.P. Singh, Mater. Sci. Eng. C, 105, 110119 (2019); https://doi.org/10.1016/j.msec.2019.110119
  45. J.H. Pandya, M. Travadi, R.N. Jadeja, R.N. Patel and V.K. Gupta, J. Indian Chem. Soc., 99, 100403 (2022); https://doi.org/10.1016/j.jics.2022.100403
  46. K. Sharma, D.P. Singh and V. Kumar, Indian J. Chem. Technol., 24, 534 (2017).
  47. M. Tyagi, S. Chandra and P. Tyagi, Spectrochim. Acta A Mol. Biomol. Spectrosc., 117, 1 (2014); https://doi.org/10.1016/j.saa.2013.07.074
  48. A. Singh and A. Chaudhary, Bioinorg. Chem. Appl., 2018, 2467463 (2018); https://doi.org/10.1155/2018/2467463
  49. O.P. Sharma and T.K. Bhat, Food Chem., 113, 1202 (2009); https://doi.org/10.1016/j.foodchem.2008.08.008
  50. C.G.P. Doss and N. Nagasundaram, PLoS One, 7, e31677 (2012);https://doi.org/10.1371/journal.pone.0031677
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