Dithiocarbazate Ligand-Based Cu(II), Ni(II), and Zn(II) Complexes: Synthesis, Structural Investigations, Cytotoxicity, DNA Binding, and Molecular Docking Studies

Enis Nadia Md Yusof; Mohammad Azam; Siti Syaida Sirat; Thahira B S A Ravoof; Alister J Page; Abhi Veerakumarasivam; Thiruventhan Karunakaran; Mohd Rizal Razali

doi:10.1155/2022/2004052

Dithiocarbazate Ligand-Based Cu(II), Ni(II), and Zn(II) Complexes: Synthesis, Structural Investigations, Cytotoxicity, DNA Binding, and Molecular Docking Studies

Bioinorg Chem Appl. 2022 Jul 31:2022:2004052. doi: 10.1155/2022/2004052. eCollection 2022.

Authors

Enis Nadia Md Yusof¹, Mohammad Azam², Siti Syaida Sirat³, Thahira B S A Ravoof⁴, Alister J Page⁵, Abhi Veerakumarasivam^{6

7}, Thiruventhan Karunakaran^{8

9}, Mohd Rizal Razali⁹

Affiliations

¹ Chemistry Section, School of Distance Education, Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, Malaysia.
² Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
³ Faculty of Applied Sciences, Universiti Teknologi MARA, Cawangan Negeri Sembilan, Kampus Kuala Pilah, Kuala Pilah 72000, Negeri Sembilan, Malaysia.
⁴ Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Seri Kembangan, Selangor, Malaysia.
⁵ Discipline of Chemistry, School of Environmental and Life Sciences, University of Newcastle, University Drive, Callaghan, Newcastle, NSW 2308, Australia.
⁶ Department of Biological Sciences, School of Medical and Life Sciences, Sunway University, No. 5 Jalan Universiti, 47500 Bandar Sunway, Petaling Jaya, Selangor Darul Ehsan, Malaysia.
⁷ Medical Genetics Laboratory, Faculty of Medicine and Health Sciences, Universiti Putra Malaysia, 43400 UPM Serdang, Seri Kembangan, Selangor Darul Ehsan, Malaysia.
⁸ Centre for Drug Research, Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, Malaysia.
⁹ School of Chemical Sciences, Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, Malaysia.

Abstract

S-4-methylbenzyl-β-N-(2-methoxybenzylmethylene)dithiocarbazate ligand, 1, prepared from S-(4-methylbenzyl)dithiocarbazate, was used to produce a novel series of transition metal complexes of the type, [M (L)₂] [M = Cu(II) (2), Ni(II) (3), and Zn(II) (4), L = 1]. The ligand and its complexes were investigated by elemental analysis, FTIR, ¹H and ¹³C-NMR, MS spectrometry, and molar conductivity. In addition, single X-ray crystallography was also performed for ligand, 1, and complex 3. The Hirshfeld surface analyses were also performed to know about various bonding interactions in the ligand, 1, and complex 3. The investigated compounds were also tested to evaluate their cytotoxic behaviour. However, complex 2 showed promising results against MCF-7 and MDA-MB-213 cancer cell lines. Furthermore, the interaction of CT-DNA with ligand, 1, and complex 2 was also studied using the electronic absorption method, revealing that the compounds have potential DNA-binding ability via hydrogen bonding and hydrophobic and van der Waals interactions. A molecular docking study of complex 2 was also carried out, which revealed that free binding free energy value was -7.39 kcal mol^-1.