Issue

Vol. 34 No. 3 (2022): Vol 34 Issue 3, 2022

Copyright (c) 2022 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Antimicrobial, Cytotoxicity and Molecular Docking Study of New Quinoline Schiff Base and its Metal(II) Complexes

https://doi.org/10.14233/ajchem.2022.23301
B.T. Vibhute
Department of Chemistry, Changu Kana Thakur Arts, Commerce and Science College, New Panvel-Raigad, Navi Mumbai-410206, India
B.D. Aghav
Department of Chemistry, Changu Kana Thakur Arts, Commerce and Science College, New Panvel-Raigad, Navi Mumbai-410206, India
B.P. More
Department of Chemistry, M.V.P. Samaj’s Arts, Commerce and Science College, Nandgaon-423106, India
R.O. Bellamkonda
Department of Chemistry, Sreyas Institute of Engineering and Technology, Bandlaguda, Nagole-500068, India
S.K. Patil
Department of Chemistry, Changu Kana Thakur Arts, Commerce and Science College, New Panvel-Raigad, Navi Mumbai-410206, India

Corresponding Author(s) : B.T. Vibhute

vbtchem@gmail.com

Asian Journal of Chemistry, Vol. 34 No. 3 (2022): Vol 34 Issue 3, 2022

Abstract

A new quinoline Schiff base ligand was synthesized by the reaction of 2-hydroxy-7-methylquinolin-3-carbaldehyde and 4-methylbenzene sulfonohydrazide. Synthesized Schiff base further utilized for the formation of stable metal complexes with Cu(II), Ni(II), Co(II) and Cd(II) metal salts and characterized by different spectroscopic techniques i.e. 1H NMR, 13C NMR, FT-IR, UV-visible, ESR, MASS and TGA. The low molar conductance values indicate that synthesized metal(II) complexes were non-electrolytes. The magnetic moment value indicates that Cu(II), Ni(II) and Co(II) complexes were paramagnetic. Further, these compounds were screened for inhibition activity against four bacterial strains, three fungal strains and cytotoxicity against the A-549 and MCF-7 cell lines by using the MTT method. Among the synthesized complexes, metal complexes exhibited excellent anticancer activity against the human lung cancer cell line (A-549). Schiff base and its Cd(II) complex showed good antibacterial activity. Furthermore, molecular docking study shows the significant binding affinity of metal complexes with tubulin protein. Present study proposed that all the synthesized Schiff base metal(II) complexes have excellent biological activity and could be act as potential anticancer agents.

Keywords

Schiff base Sulfonohydrazide Quinoline MIC Cytotoxicity
Vibhute, B., Aghav, B., More, B., Bellamkonda, R., & Patil, S. (2022). Antimicrobial, Cytotoxicity and Molecular Docking Study of New Quinoline Schiff Base and its Metal(II) Complexes. Asian Journal of Chemistry, 34(3), 685–694. https://doi.org/10.14233/ajchem.2022.23301
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. S.A. Sadeek, M.S. El-Attar and S.M. Abd El-Hamid, J. Mol. Struct., 1051, 30 (2013); https://doi.org/10.1016/j.molstruc.2013.07.053
  2. B. Vivekanand, K. Mahendra Raj and B.H.M. Mruthyunjayaswamy, J. Mol. Struct., 1079, 214 (2015); https://doi.org/10.1016/j.molstruc.2014.08.033
  3. E. Labisbal, J.A. Garcia-Vazquez, J. Romero, S. Picos, A. Sousa, A. Castiñeiras and C. Maichle-Mössmer, Polyhedron, 14, 663 (1995); https://doi.org/10.1016/0277-5387(94)00292-M
  4. S.A. Beyramabadi, B. Esmaeili, A. Gharib, M. Khorsandi-Chenarboo, A. Morsali, M. Khashi and R. Sanavi-Khoshnood, J. Mol. Struct., 1146, 620 (2017); https://doi.org/10.1016/j.molstruc.2017.06.050
  5. A. Beyramabadi, A. Morsali, M.J. Khoshkholgh and A.A. Esmaeili, Spectrochim. Acta A Mol. Biomol. Spectrosc., 83, 467 (2011); https://doi.org/10.1016/j.saa.2011.08.067
  6. M. Habibi, S.A. Beyramabadi, S. Allameh, M. Khashi, A. Morsali, M. Pordel and M. Khorsandi Chenarboo, J. Mol. Struct., 1143, 424 (2017); https://doi.org/10.1016/j.molstruc.2017.04.114
  7. T. Toozandejani, S.A. Beyramabadi, H. Chegini, M. Khashi, A. Morsali and M. Pordel, J. Mol. Struct., 1127, 15 (2017); https://doi.org/10.1016/j.molstruc.2016.07.026
  8. M. Yavari, S.A. Beyramabadi, A. Morsali and M.R. Bozorgmehr, J. Struct. Chem., 59, 1102 (2018); https://doi.org/10.1134/S0022476618050128
  9. A.A. Abdel Aziz, F.M. Elantabli, H. Moustafa and S.M. El-Medani, J. Mol. Struct., 1141, 563 (2017); https://doi.org/10.1016/j.molstruc.2017.03.081
  10. E.G. Bakirdere, M.F. Fellah, E. Canpolat, M. Kaya and S. Gür, J. Serb. Chem. Soc., 81, 509 (2016); https://doi.org/10.2298/JSC151030008B
  11. S. Dutta Gupta, B. Revathi, G.I. Mazaira, M.D. Galigniana, C.V.S. Subrahmanyam, N.L. Gowrishankar and N.M. Raghavendra, Bioorg. Chem., 59, 97 (2015); https://doi.org/10.1016/j.bioorg.2015.02.003
  12. S.A. Elsayed, A.M. Noufal and A.M. El-Hendawy, J. Mol. Struct., 1144, 120 (2017); https://doi.org/10.1016/j.molstruc.2017.05.020
  13. S.H. Sumrra, S. Kausar, M.A. Raza, M. Zubair, M.N. Zafar, M.A. Nadeem, E.U. Mughal, Z.H. Chohan, F. Mushtaq and U. Rashid, J. Mol. Struct., 1168, 202 (2018); https://doi.org/10.1016/j.molstruc.2018.05.036
  14. P. Tyagi, S. Chandra, B.S. Saraswat and D. Yadav, Spectrochim. Acta A Mol. Biomol. Spectrosc., 145, 155 (2015); https://doi.org/10.1016/j.saa.2015.03.034
  15. C. Chandramouli, M. Shivanand, T. Nayanbhai, B. Bheemachari and R. Udupi, J. Chem. Pharm. Res., 4, 1151 (2012).
  16. B.S. Creaven, M. Devereux, D. Karcz, A. Kellett, M. McCann, A. Noble and M. Walsh, J. Inorg. Biochem., 103, 1196 (2009); https://doi.org/10.1016/j.jinorgbio.2009.05.017
  17. A.R. Gholap, K.S. Toti, F. Shirazi, R. Kumari, M.K. Bhat, M.V. Deshpande and K.V. Srinivasan, Bioorg. Med. Chem., 15, 6705 (2007); https://doi.org/10.1016/j.bmc.2007.08.009
  18. R. Joshi, A. Kumari, K. Singh, H. Mishra and S. Pokharia, J. Mol. Struct., 1197, 519 (2019); https://doi.org/10.1016/j.molstruc.2019.07.066
  19. H. Vural and Ö. Idil, J. Mol. Struct., 1177, 242 (2019); https://doi.org/10.1016/j.molstruc.2018.09.070
  20. E. Khan, M. Hanif and M.S. Akhtar, Rev. Inorg. Chem., (2021); https://doi.org/10.1515/revic-2021-0034
  21. F. Ghasedian, H. Zamani, F. Joz-Yarmohammadi, S. Beyramabadi and M. Abedi, Russ. J. Appl. Chem., 89, 2001 (2016); https://doi.org/10.1134/S1070427216120119
  22. S. Calus, E. Gondek, A. Danel, B. Jarosz, M. Pokladko and A. Kityk, Mater. Lett., 61, 3292 (2007); https://doi.org/10.1016/j.matlet.2006.11.055
  23. A. Soroceanu, M. Cazacu, S. Shova, C. Turta, J. Ko•íšek, M. Gall, M. Breza, P. Rapta, T.C.O. Mac Leod, A.J.L. Pombeiro, J. Telser, A.A. Dobrov and V.B. Arion, Eur. J. Inorg. Chem., 2013, 1458 (2013); https://doi.org/10.1002/ejic.201201080
  24. F. Jafari-Moghaddam, S.A. Beyramabadi, M. Khashi and A. Morsali, J. Mol. Struct., 1153, 149 (2018); https://doi.org/10.1016/j.molstruc.2017.10.007
  25. C.C. Roberts, B.R. Barnett, D.B. Green and J.M. Fritsch, Organometallics, 31, 4133 (2012); https://doi.org/10.1021/om200865w
  26. Z.A. Siddiqi, M. Khalid, S. Kumar, M. Shahid and S. Noor, Eur. J. Med. Chem., 45, 264 (2010); https://doi.org/10.1016/j.ejmech.2009.10.005
  27. Z.-C. Liu, B.-D. Wang, B. Li, Q. Wang, Z.-Y. Yang, T.-R. Li and Y. Li, Eur. J. Med. Chem., 45, 5353 (2010); https://doi.org/10.1016/j.ejmech.2010.08.060
  28. P. Hewawasam, W. Fan, J. Knipe, S.L. Moon, C.G. Boissard, V.K. Gribkoff and J.E. Starrett Jr., Bioorg. Med. Chem. Lett., 12, 1779 (2002); https://doi.org/10.1016/S0960-894X(02)00240-8
  29. M.A. Abd-Alla, A.-H.N. Ahmed, M.F. El-Zohry and F.A. Omar, Collect. Czech. Chem. Commun., 57, 1547 (1992); https://doi.org/10.1135/cccc19921547
  30. B.S. Holla, M. Mahalinga, M.S. Karthikeyan, P.M. Akberali and N.S. Shetty, Bioorg. Med. Chem., 14, 2040 (2006); https://doi.org/10.1016/j.bmc.2005.10.053
  31. M. Andaloussi, E. Moreau, N. Masurier, J. Lacroix, R.C. Gaudreault, J.-M. Chezal, A. El Laghdach, D. Canitrot, E. Debiton, J.-C. Teulade and O. Chavignon, Eur. J. Med. Chem., 43, 2505 (2008); https://doi.org/10.1016/j.ejmech.2008.02.017
  32. P. Rani, V. Srivastava and A. Kumar, Eur. J. Med. Chem., 39, 449 (2004); https://doi.org/10.1016/j.ejmech.2003.11.002
  33. N. Hamdi, C. Lidrissi, M. Saoud, A. Romerosa Nievas and H. Zarrouk, Chem. Heterocycl. Compd., 42, 320 (2006); https://doi.org/10.1007/s10593-006-0088-0
  34. G. Paolucci, A. Zanella, L. Sperni, V. Bertolasi, M. Mazzeo and C. Pellecchia, J. Mol. Catal. Chem., 258, 275 (2006); https://doi.org/10.1016/j.molcata.2006.05.043
  35. J.-Q. Wu, L. Pan, Y.-G. Li, S.-R. Liu and Y.-S. Li, Organometallics, 28, 1817 (2009); https://doi.org/10.1021/om801028g
  36. X. Wang, R. Fan, Y. Dong, T. Su, J. Huang, X. Du, P. Wang and Y. Yang, Cryst. Growth Des., 17, 5406 (2017); https://doi.org/10.1021/acs.cgd.7b00891
  37. B.M. Mistry, S.K. Sahoo and S. Jauhari, J. Electroanal. Chem., 704, 118 (2013); https://doi.org/10.1016/j.jelechem.2013.07.004
  38. S.K. Patil and B.T. Vibhute, Arab. J. Chem., 14, 103285 (2021); https://doi.org/10.1016/j.arabjc.2021.103285
  39. S. Adsule, V. Barve, D. Chen, F. Ahmed, Q.P. Dou, S. Padhye and F.H. Sarkar, J. Med. Chem., 49, 7242 (2006); https://doi.org/10.1021/jm060712l
  40. A. Srivastava and R.M. Singh, Indian J. Chem., 44A, 1868 (2005).
  41. I. Wiegand, K. Hilpert and R.E.W. Hancock, Nat. Protoc., 3, 163 (2008); https://doi.org/10.1038/nprot.2007.521
  42. H.R. Rajabi, R. Naghiha, M. Kheirizadeh, H. Sadatfaraji, A. Mirzaei and Z.M. Alvand, Mater. Sci. Eng. C, 78, 1109 (2017); https://doi.org/10.1016/j.msec.2017.03.090
  43. G.M. Morris, R. Huey, W. Lindstrom, M.F. Sanner, R.K. Belew, D.S. Goodsell and A.J. Olson, J. Comput. Chem., 30, 2785 (2009); https://doi.org/10.1002/jcc.21256
  44. R.H. Wade and A.A. Hyman, Curr. Opin. Cell Biol., 9, 12 (1997); https://doi.org/10.1016/S0955-0674(97)80146-9
  45. R.A. Stanton, K.M. Gernert, J.H. Nettles and R. Aneja, Med. Res. Rev., 31, 443 (2011); https://doi.org/10.1002/med.20242
  46. BIOVIA DS, Discovery Studio Modeling Environment, Release 2017, San Diego. In: Dassault Systèmes (2016).
  47. W.L. DeLano, The PyMOL Molecular Graphics System, Version 1.1. Schrödinger LLC (2002).
  48. M. Pervaiz, I. Ahmad, M. Yousaf, S. Kirn, A. Munawar, Z. Saeed, A. Adnan, T. Gulzar, T. Kamal, A. Ahmad and A. Rashid, Spectrochim. Acta A Mol. Biomol. Spectrosc., 206, 642 (2019); https://doi.org/10.1016/j.saa.2018.05.057
  49. N. Raman, A. Kulandaisamy and K. Jeyasubramanian, Synth. React. Inorg. Met.-Org. Chem., 31, 1249 (2001); https://doi.org/10.1081/SIM-100106862
  50. N. Sari, S. Arslan, E. Logoglu and I. Sakiyan, J. Am. Sci., 16, 283 (2003).
  51. G. Mohamed and Z. Abd El-Wahab, J. Therm. Anal. Calorim., 73, 347 (2003); https://doi.org/10.1023/A:1025126801265
  52. A.S. Salameh and H.A. Tayim, Polyhedron, 2, 829 (1983); https://doi.org/10.1016/S0277-5387(00)87213-7
  53. H.S. Seleem, B.A. El-Shetary and M. Shebl, Heteroatom Chem., 18, 100 (2007); https://doi.org/10.1002/hc.20239
  54. M. Shebl and S.M.E. Khalil, Monatsh. Chem., 146, 15 (2015); https://doi.org/10.1007/s00706-014-1302-x
  55. M. Shebl, J. Coord. Chem., 62, 3217 (2009); https://doi.org/10.1080/00958970903012785
  56. M. Shebl, J. Mol. Struct., 1128, 79 (2017); https://doi.org/10.1016/j.molstruc.2016.08.056
  57. P. Tyagi, S. Chandra and B.S. Saraswat, Spectrochim. Acta A Mol. Biomol. Spectrosc., 134, 200 (2015); https://doi.org/10.1016/j.saa.2014.06.112
  58. D.P. Singh, R. Kumar, V. Malik and P. Tyagi, Transition Met. Chem., 32, 1051 (2007); https://doi.org/10.1007/s11243-007-0279-2
  59. N.N. Greenwood and A. Earnshaw, Chemistry of the Elements, Heimemann: Oxford, UK, Ed.: 2 (1997).
  60. T.R. Rao and A. Prasad, Met.-Org. Nano-Met. Chem., 35, 299 (2005); https://doi.org/10.1081/SIM-200055245
  61. B.T. Thaker, P.K. Tandel, A.S. Patel, C.J. Vyas, M.S. Jesani and D.M. Patel, Indian J. Chem., 44A, 265 (2005).
  62. G. Reddy, S. Balasubramanian and K. Chennakesavulu, J. Mater. Chem. A Mater. Energy Sustain., 2, 19102 (2014); https://doi.org/10.1039/C4TA90172J
  63. H.F. El-Shafiy and M. Shebl, J. Mol. Struct., 1156, 403 (2018); https://doi.org/10.1016/j.molstruc.2017.11.081
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 1 Download : 0