Synthesis, DNA Binding Affinity, Molecular Docking Study and Antitumor Activity of Cu(II), Pd(II) and Zn(II) Metal Complexes of Benzimidazole Schiff Base Ligand. | [Journal of Chemical Society of Pakistan • 2019]

Author(s):

1. Khalid Mahmood: Department of Chemistry, Quaid-i-Azam University Islamabad, Pakistan

2. Zareen Akhter: Department of Biochemistry, Quaid-i-Azam University Islamabad, Pakistan

3. Bushra Mirza: Department of Biochemistry, University of Gujrat, Gujrat, Pakistan

4. Hammad Ismail: Department of Biochemistry, University of Gujrat, Gujrat, Pakistan

5. Faroha Liaqat: Department of Chemistry, Quaid-i-Azam University Islamabad, Pakistan

6. Saima Kalsoom: Center for Interdisciplinary Research in Basic Sciences (CIRBS), International Islamic University, Islamabad, Pakistan

7. Ahmad Raza Ashraf: Department of Chemistry, Quaid-i-Azam University Islamabad, Pakistan

8. Muhammad Abdul Qayyum: Department of Chemistry, University of Education (Lahore), Faisalabad campus. Faislabad, Pakistan

Abstract:

Summary: Benzimidazole Schiff base ligand (E)-2-bromo-4-chloro-6-((4-(6-fluoro-1Hbenzo[d]imidazol-2-yl)phenylimino)methyl)phenol (1) and corresponding Cu(II) (2), Pd(II) (3) and Zn(II) (4) complexes were synthesized successfully. The structural elucidations were carried out by FTIR and NMR (1H NMR and 13C NMR) spectroscopic techniques while molecular formulae and stoichiometry were confirmed by ESI/MALDI mass spectral analyses. We presented the biological worth of the synthesized compounds. UV-vis absorption spectroscopy provided strong evidence of interaction with salmon sperm DNA (SS-DNA), allowing us to calculate the intrinsic binding constant (Kb), equal to 2.33×105, 3.38×105, 1.1×105, 6.9×104 M-1 for 1, 2, 3 and 4 respectively. The preferential affinity order was further verified by thermal melting (Tm) of DNA. In the presence of compounds 1, 2, 3 and 4, Tm value of DNA (68.5°C for pure DNA) was increased to 75.0, 75.4, 71.0 and 73.2°C respectively. Results were highly coherent with absorption titrations, proving complex 2 an efficient DNA intercalator. Molecular docking was carried out to evaluate the interaction of the synthesized compounds with double-stranded DNA both in vitro and in silico. The investigations showed a correlation between binding constants and activity, indicating the development of highly active compounds. The synthetic probes were screened for preliminary antineoplastic activity against Agrobacterium tumefaciens induced tumors in potato discs. Every compound displayed tumor inhibition activity, especially 2 inhibited up to 60% tumors with IC50 value equal to 0.3 mg/ml. Nontoxic nature of synthesized compounds was confirmed by exerting no considerable life-threatening effect on Artemia cells when exposed even to their higher concentration.

Page(s): 903-916

DOI: DOI not available

Published: Journal: Journal of Chemical Society of Pakistan, Volume: 41, Issue: 5, Year: 2019

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