Advertisement

DNA Binding, Molecular Docking and Antimicrobial Evaluation of Novel Azo Dye Ligand and Their Metal Complexes

  • N. Venugopal
  • G. KrishnamurthyEmail author
  • H. S. Bhojya Naik
  • J. D. Manohara
Article
First Online:
  • 41 Downloads

Abstract

In the present work, the synthesis of novel azo dye ligand 6-hydroxy-4-methyl-2-oxo-1-propyl-5-[(E)-1,3-thiazol-2-yldiazenyl]-1,2-dihydropyridine-3-carbonitrile (L) and its Cu(II), Co(II) and Ni(II) transition complexes were prepared. The newly formed compounds were characterized by elemental analysis, UV–Vis, FT-IR, 1H NMR, LC–MS, TGA and magnetic susceptibility measurement. The molar conductance indicates that all the metal complexes are non-electrolytic in nature Based on spectral data indicate square planar geometry was deduced for Cu(II) and Ni(II) complexes, Co(II) complex has tridentate chelation of ligand and produce an octahedral geometry around the metal ion. Additionally, the computational study has been performed using density functional theory (DFT) calculation was used to study the electronic structure of synthesized ligand and their complexes. The in vitro antimicrobial activity of the azo dye ligand and its complexes was tested against Gram +ve bacteria (Bacillus subtilis), Gram –ve bacteria (Escherichia coli), yeast (Candida albicans) and fungus (Aspergillus flavus). All the complexes showed enhanced biocidal activity compared to the free ligand. Moreover, azo dye ligand and its metal complexes have been studied for their antioxidant activity. The DNA-binding activity of metal complexes (1a–1c) was studied by electronic absorption spectroscopy and fluorescence spectroscopy. All the complexes bound to CT-DNA through an intercalation mode. Additionally, all the metal complexes act as good cleavage agents against the pBR322 DNA. The computer-aided molecular docking studies of metal complexes with the receptor of GlcN-6-P synthase showed that metal complexes are potent drugs for the target enzymes.

Keywords

Azo dye Metal chelates TGA DFT DNA binding Molecular docking 
This is a preview of subscription content, log in to check access.

Notes

Supplementary material

10904_2019_1394_MOESM1_ESM.docx (529 kb)
Supplementary material 1 (DOCX 529 kb)

References

  1. 1.
    M. Gaber, S.K. Fathalla, H.A. El-Ghamry, Appl. Organomet. Chem. 33, e4707 (2019)CrossRefGoogle Scholar
  2. 2.
    F.A. Saad, H.A. El-Ghamry, M.A. Kassem, Appl. Organomet. Chem. 33, 4965 (2019)CrossRefGoogle Scholar
  3. 3.
    A.Z. El-Sonbati, M.A. Diab, A.A. El-Bindary, A.F. Shoair, N.M. Beshry, J. Mol. Liq. 218, 400–420 (2016)CrossRefGoogle Scholar
  4. 4.
    A. Tupys, J. Kalembkiewicz, Y. Ostapiuk, V.M.O. Tymoshuk, E. Woz nicka, L. Byczyn ski, J. Therm. Anal. Calorim. 127, 2233–2242 (2017)CrossRefGoogle Scholar
  5. 5.
    A. Penchev, D. Simov, N. Gadjev, Dyes Pigm. 16, 77 (1991)CrossRefGoogle Scholar
  6. 6.
    A.Z. El-Sonbati, G.G. Mohamed, A.A. El-Bindary, W.M.I. Hassan, A.K. Elkholy, J. Mol. Liq. 209, 625–634 (2015)CrossRefGoogle Scholar
  7. 7.
    S.H. Alotaibi, A.S. Radwan, Y.K. Abdel-Monem, M.M. Makhlouf, Spectrochim. Acta A. 205, 364–375 (2018)CrossRefGoogle Scholar
  8. 8.
    Ö.F. Öztürk, Trans. Met. Chem. 32, 224–227 (2007)CrossRefGoogle Scholar
  9. 9.
    K.J. AL-Adilee, A.K. Abass, A.M. Taher, J. Mol. Struct. (2016).  https://doi.org/10.1016/j.molstruc.2015.11.038 CrossRefGoogle Scholar
  10. 10.
    J. Joseph, B.H. Mehta, Russ. J. Coord. Chem. 33, 124–129 (2007)CrossRefGoogle Scholar
  11. 11.
    Fawaz A. Saad, Hoda A. El-Ghamry, M.A. Kassem, Appl. Organomet. Chem. 33, 4965 (2019)CrossRefGoogle Scholar
  12. 12.
    K. Singh, M.S. Barwa, P. Tyagi, Eur. J. Med. Chem. 42, 394–402 (2007)PubMedCrossRefGoogle Scholar
  13. 13.
    S.S. Chavan, V.A. Sawant, J. Mol. Struct. 965, 1–6 (2010)CrossRefGoogle Scholar
  14. 14.
    K.J. Al-Adilee, B.A. Hatem, J. Adv. Chem. 11(3), 3412–3425 (2015)CrossRefGoogle Scholar
  15. 15.
    S. Dhar, D. Senapati, P.K. Das, P. Chatopadhyay, M. Nethaji, A.R. Chakravarty, J. Am. Chem. Soc. 125, 12118–12124 (2003)PubMedCrossRefGoogle Scholar
  16. 16.
    N. Chitrapriya, V. Mahalingam, M. Zeller, K. Natarajan, Inorg. Chim. Acta 363, 3685 (2010)CrossRefGoogle Scholar
  17. 17.
    M. Sirajuddin, N. Uddin, S. Ali, M.N. Tahir, Mol. Biomol. Spectrosc. 111, 116 (2013)Google Scholar
  18. 18.
    S. Kathiresan, S. Mugesh, J. Annaraj, M. Murugan, New J. Chem. 41, 1267 (2017)CrossRefGoogle Scholar
  19. 19.
    H. Xu, K.C. Zheng, Y. Chen, Y.Z. Li, L.J. Lin, H. Li, P.X. Zhang, L.N. Ji, Dalton Trans. 3, 2260–2268 (2003)CrossRefGoogle Scholar
  20. 20.
    R. Kramer, Coord. Chem. Rev. 182, 243–261 (1999)CrossRefGoogle Scholar
  21. 21.
    R.F. Tabor, T.M. McCoy, H. Yingxue, B.L. Wilkinson, Bull. Chem. Soc. Jpn 91, 932–939 (2018)CrossRefGoogle Scholar
  22. 22.
    P. Weis, S. Wu, Macromol. Rapid Commun. 39, 1700220 (2018)CrossRefGoogle Scholar
  23. 23.
    N. Venugopal, G. Krishnamurthy, H.S. Bhojyanaik, P. Murali Krishna, J. Mol. Struct. 183, 37–51 (2019)CrossRefGoogle Scholar
  24. 24.
    W. You, H.-Y. Zhu, W. Huang, B. Hu, Y. Fan, X.-Z. You, Dalton Trans. 39, 7876–7880 (2010)PubMedCrossRefGoogle Scholar
  25. 25.
    B.G. Devika, B.H. Doreswamy, N.M. Mallikarjuna, H.C. Tandon, J. Mol. Struct. (2019).  https://doi.org/10.1016/j.molstruc.2019.02.029 CrossRefGoogle Scholar
  26. 26.
    S. Yousef-Ebrahimipour, I. Sheikhshoaie, J. Castro, M. Dusek, Z. Tohidian, V. Eigner, M. Khaleghi, RSC Adv. (2015).  https://doi.org/10.1039/c5ra17524k CrossRefGoogle Scholar
  27. 27.
    A. Vogel, Textbook of Practical Organic Chemistry, 5th edn. (Longman Group, London, 1989)Google Scholar
  28. 28.
    M.J. Frisch, Gaussian 09, Revision A02 (Gaussian Inc., Wallingford, 2009)Google Scholar
  29. 29.
    A.D. Becke, J. Chem. Phys. 98, 5648 (1993)CrossRefGoogle Scholar
  30. 30.
    M.F. Reichmann, S.A. Rice, C.A. Thomas, P. Doty, J. Am. Chem. Soc. 76, 3047 (1954)CrossRefGoogle Scholar
  31. 31.
    A. Blask, T.C. Bruice, Acc. Chem. Res. 32, 475–484 (1999)CrossRefGoogle Scholar
  32. 32.
    A.A.A. Aziz, S.H. Seda, J Fluoresc 27, 1051–1066 (2017)PubMedCrossRefPubMedCentralGoogle Scholar
  33. 33.
    A. Bauer, W. Kirby, J. Sherris, M. Turck, Am. J. Clin. Pathol. 45, 493 (1966)PubMedCrossRefPubMedCentralGoogle Scholar
  34. 34.
    M. Pfaller, L. Burmeister, M. Bartlett, M. Rinaldi, J. Clin. Microbiol. 26, 1437 (1988)PubMedPubMedCentralGoogle Scholar
  35. 35.
    H. Wu, J. Kong, Z. Yang, X. Wang, F. Shi, Y. Zhang, Trans. Met. Chem. 39, 951–960 (2014)CrossRefGoogle Scholar
  36. 36.
    X. Qiu, S. Abdel-Meguid, C. Janson, R. Court, M. Smyth, D. Payne, Protein Sci. 8, 2529 (1999)PubMedPubMedCentralCrossRefGoogle Scholar
  37. 37.
    S. Mouilleron, M.A. Badet-Denisot, B. Golinelli-Pimpaneau, J. Mol. Biol. 377(4), 1174–1185 (2008)PubMedCrossRefPubMedCentralGoogle Scholar
  38. 38.
    W. Geary, Coord. Chem. Rev. 81, 7 (1971)Google Scholar
  39. 39.
    F.A. Saad, J.H. Al-Fahemi, H. El-Ghamry, A.M. Khedr, M.G. Elghalban, N.M. El-Metwaly, J. Therm. Anal. Calorim. 131, 1249–1267 (2018)CrossRefGoogle Scholar
  40. 40.
    A.Z. Sonbati, G.G. Mohamed, A.A. Bindary, W.M.I. Hassan, M.A. Diab, S.M. Morgan, A.K. Elkholy, J. Mol. Liq. 212, 487–502 (2015)CrossRefGoogle Scholar
  41. 41.
    M.S. Masoud, S.S. Hagagg, Alaa E. Ali, N.M. Nsar, J. Mol. Struct. 1014, 17–25 (2012)CrossRefGoogle Scholar
  42. 42.
    X. He, J.J. Liu, H.M. Guo, M. Shao, M.X. Li, Polyhedron 29, 1062 (2010)CrossRefGoogle Scholar
  43. 43.
    K.Y. El-Baredie, Monatsh. Chem. 136, 1139 (2005)CrossRefGoogle Scholar
  44. 44.
    H. Liu, H. Wang, F. Gao, D. Niu, Z. Lu, J. Coord. Chem. 60, 2671–2678 (2007)CrossRefGoogle Scholar
  45. 45.
    N. Venugopal, G. Krishnamurthy, H.S. Bhojyanaik, M. Giridhar, J. Mol. Struct. 1191, 85–94 (2019)CrossRefGoogle Scholar
  46. 46.
    D.N. Sathyanarayana, Electronic Absorption Spectroscopy and Related Technique (University Press (India), Hyderabad, 2001)Google Scholar
  47. 47.
    Song H, Chen K, Tian, H, Dyes Pigm. 53, 257–262 (2002)CrossRefGoogle Scholar
  48. 48.
    N. Lotfi, I. Sheikhshoaei, S.Y. Ebrahimipour, H. Krautscheid, J. Mol. Struct. 432, 1149 (2017)Google Scholar
  49. 49.
    W.H. Mahmoud, N.F. Mahmoud, G.G. Mohamed, Appl. Organomet. Chem. 1, 31 (2017)Google Scholar
  50. 50.
    I. Fleming, Frontier Orbitals and Organic Chemical Reactions (Wiley, New York, 1976)Google Scholar
  51. 51.
    W.H. Mahmoud, R.G. Deghadi, G.G. Mohamed, J. Therm. Anal. Calorim. 127(3), 2149 (2016)CrossRefGoogle Scholar
  52. 52.
    P. Thanikaivelan, V. Subramanian, J.R. Rao, B.U. Nair, Chem. Phys. Lett. 59, 323 (2000)Google Scholar
  53. 53.
    K. Dhahagani, M.P. Kesavan, G.G.V. Kumar, L. Ravi, G. Rajagopal, J. Rajesh, Mater. Sci. Eng. (2018).  https://doi.org/10.1016/j.msec.2018.04.032 CrossRefGoogle Scholar
  54. 54.
    N. Deepika, Y.P. Kumar, C.S. Devi, P.V. Reddy, A. Srishailam, S. Satyanarayana, J. Biol. Inorg. Chem. (2013).  https://doi.org/10.1007/s00775-013-1018-0 CrossRefPubMedGoogle Scholar
  55. 55.
    J. Chen, X. Wang, Y. Shao, J. Zhu, Y. Zhu, Y. Li, Q. Xu, Z.J. Guo, Inorg. Chem. 46, 3306–3312 (2007)PubMedCrossRefGoogle Scholar
  56. 56.
    R. Ramesh, S. Maheswaran, J. Inorg. Biochem. 9, 457–462 (2003)CrossRefGoogle Scholar
  57. 57.
    K.R. Sangeetha Gowda, H.S. Bhojya Naik, B. Vinay-Kumar, C.N. Sudhamani, H.V. Sudeep, T.R. Ravikumar Naik, G. Krishnamurthy, Spectrochim. Acta A. 105, 229–237 (2013)CrossRefGoogle Scholar
  58. 58.
    N. Dharmaraj, P. Viswanathamurthi, K. Nataraj, Trans. Met. Chem. 26, 105–109 (2001)CrossRefGoogle Scholar
  59. 59.
    A.G. Bharathi Dileepan, T. Daniel Prakash, A. Ganesh Kumar, P. Shameela Rajam, V. Violet Dhayabaran, R. Rajaram, J. Photochem. Photobiol. Sci. (2018).  https://doi.org/10.1016/j.jphotobiol.2018.04.029 CrossRefGoogle Scholar
  60. 60.
    M.A. Gyamfi, M. Yonamine, Y. Aniya, Gen. Pharmacol. 32, 661–667 (1999)CrossRefGoogle Scholar
  61. 61.
    G. Marinova, V. Batchvarov, Bulg. J. Agric. Sci. 17, 11–24 (2011)Google Scholar
  62. 62.
    T. Manjuraj, G. Krishnamurthy, Y.D. Bodke, H.S. Bhojya-Naik, J. Mol. Struct. 1148, 231–237 (2017)CrossRefGoogle Scholar
  63. 63.
    B. Koohshekan, A. Divsalar, M. Saiedifar, A.A. Saboury, B. Ghalandari, A. Gholamian, A. Seyedarabi, J. Mol. Liq. 216, 8–15 (2016)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department of Chemistry, Sahyadri Science CollegeKuvempu UniversityShivamoggaIndia
  2. 2.Department of Industrial ChemistryKuvempu UniversityShivamoggaIndia
  3. 3.Department of ChemistryManipal Institute of Technology, Manipal Academy of Higher EducationManipalIndia

Personalised recommendations

Cite article

Buy options